Heritage Walks are FREE, guided interpretive walks to the most interesting historic, cultural, industrial, natural and scenic sites in Berkshire County, MA, & Litchfield County, CT.

2025 – THE 23RD ANNUAL
“HOUSATONIC HERITAGE WALKS”
Free, guided walks throughout Berkshire County, Massachusetts and Litchfield County, Connecticut.
Saturdays & Sundays on…Sept. 6 & 7, 13 & 14, 20 & 21, 27 & 28, and Oct. 4 & 5
*** Download the 2025 Heritage Walks Brochure here! (coming soon)***
We’re extremely grateful for our ‘HERITAGE WALKS’ sponsors!
SATURDAY – SEPT 6, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
1 – Salisbury, CT 9 AM to 10 AM
THE SECRETS OF DARK HOLLOW PRESERVE HIKE
Nobody knows the Salisbury Association’s Dark Hollow Preserve like Tom Key, from the Salisbury Association Land Trust, who has stewarded the land since it was acquired in 2008. The area was formerly called Spooky Hollow. This easy hike will explore the dark, spooky interior of this mysterious place. Hikers will follow the preserve’s three major trails, which wander through mixed hardwoods and pine/hemlock forest, skirting large rock outcroppings, and descending along fields and wetlands. A pleasant walk, with a few spine tingles! 1 hour–2.5 miles
Meet at the first pull off on Dark Hollow Road, coming from Farnam Road (at the south end of the trail). At the intersection of Rt 44 and Rt 41 in Lakeville, take Rt 41 heading southeast and almost immediately take a left on Farnam Road and drive 2 miles to the trailhead. To download the trail map, https://salisburyassociation.org/land-trust/hiking-trails-preserves/ GPS 41.964148, -73.417601
2 – Becket, MA 9:30 AM to 1 PM
HISTORY HIKE TO THE KEYSTONE ARCHES BRIDGES–A MOST MAGNIFICENT ENGINEERING FEAT BUILT IN THE 1840’S !
Join Dave Pierce, from the Friends of the Keystone Arches, for a hike to the first cluster of stone arch railway bridges built in America, in the 1830’s. They are impressive, breath-taking stone structures, up to 70 feet high, brilliantly revealing their ancestry in the great cathedrals of ancient Rome! NOTE–An inside tour of the Chester Railway Station Museum can be arranged after the free Heritage Walk. Donations are accepted. The Arches and the Railway Station were designated as National Historic Landmarks in 2021. 3.5 hours – 5 miles
To register- dpiercedlp@aol.com or 413-961-9166
From junction of Rts 20 & 102 in Lee, take Rt 20 east and drive 18 miles to Chester center. Meet at the Chester Railway Museum, 10 Prospect St. We will carpool 2 miles to the trailhead. GPS 42.28054, -72.97860 GOOGLE MAP
3 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
4 – New Marlborough, MA 10 AM to 12 NOON
HIKE AROUND THE BERKSHIRE NATIONAL FISH HATCHERY
The Berkshire National Fish Hatchery supports the restoration of lake trout populations in the Lower Great Lakes by supplying lake trout eggs to other federal hatcheries and rearing native brook trout for stocking in local waterways to support recreational fishing and education programs. Our walk will take us on a journey around a unique geological feature, the Kettle Loop Trail, before heading up the Pinnacle Loop Trail, which includes a 500-foot elevation climb. Along the way, we’ll pass a historic Monterey-New Marlborough town pillar, placed in 1913, and an old charcoal pit before reaching the Pinnacle summit, where you’ll enjoy fantastic views! Then we’ll take the Cellar Hole Trail, where you can see how early settlers strategically positioned their structures. We’ll then continue onto the Nature Trail, which features signs about the local wildlife and plants. For those looking for a shorter and less strenuous option, alternative hikes will be available with little elevation change. After the hike, we’ll have hotdogs and refreshments and you can take a tour of the hatchery. Hats and shirts will be available for purchase. 2 hours–3 miles
To register– info@hatcheryfriends.org or (413) 591-9295, https://hatcheryfriends.org
Meet at 240 Hatchery Road, New Marlborough. From the north in Monterey, take Rt 23 and just east of Lake Buel, take River Road to the Hatchery. If coming from the south, New Marlborough, take Rt 57/Rt 183 (Hartsville-New Marlborough Road) to the center of Hartsville, and turn right onto Hatchery Road.
5 – Gt. Barrington, MA 11 AM to 1 PM
GREAT BARRINGTON’S ARCHITECTURE & HISTORY – THE STORY OF GREAT BUILDINGS IN A GREAT TOWN
This walking tour with Nicholas Greene, from Clark, Green & BEK, will lead participants on a stroll through historic downtown Great Barrington as they discover the rich history of the town’s former and current inhabitants, their lives and the beautiful building architecture they called home. 2 hours–1 mile
To register- greenen23@gmail.com (indicate “GB Architecture Tour & Date” in the subject line). Sign up closes for the tour at 8 PM the night before the Walk
Meet at the engraved stone monument at the corner of Main and Castle Street, Great Barrington, MA. GPS 42.19378, -73.36382 GOOGLE MAP
6 – East Canaan, CT Anytime from 10 AM to 2 PM
1 HOUR TOURS OF THE BECKLEY BLAST FURNACE–CT’S DEDICATED IRON INDUSTRIAL MONUMENT
Learn about the historic iron industry of the Upper Housatonic Valley, by the Friends of Beckley Furnace. Built in 1847, the Beckley Furnace produced high quality iron until 1918, and is one of the last surviving examples of the 19th and early 20th century blast furnaces that were once commonplace sights in CT, and is listed on the National Register of Historic Places. There once were 21 furnaces in northwestern CT, as rich veins of iron ore were discovered in the hills near the town of Salisbury. During the American Revolution, CT-forged iron helped fuel the manufacture of American weaponry, most notably the cannons used by the Continental Army, Union weapons for the Civil War, and railroad car wheels. Tour begins when you arrive. 1 hour long tours–0.4 mile
140 Lower Road, East Canaan, just off US Rts 44 & 7. If coming from the East, North, or West, take Route 44 to East Canaan, CT. At the Congregational church, turn south onto Lower Road, passing alongside the Church building, and continue for approximately 1/2 mile, turning to the right and down the hill. The former furnace office and the furnace stack are visible on your left. If coming from the south, take Rte 7 to Canaan, CT. Pass a railroad yard on your left, and just before you cross a bridge across the Blackberry River, turn right into Lower Road, heading East. The Furnace is about 3 miles east of the intersection of Lower Road and East Canaan. GPS 42.0110 N, -73.2925 W
7 – New Marlborough, MA 12 NOON to 2 PM
HIKE TO CAMPBELL FALLS – WATERFALLS, WATERSHEDS AND NATURAL HISTORY OF THE BERKSHIRES
Join Erik Reardon, from the Housatonic Valley Association, for a visit to one of the most stunning scenic attractions in the Berkshires! Straddling the border between Mass. and Conn., Campbell Falls is a 50-foot high waterfall on the Whiting River, which flows south to CT, where it meets the Blackberry River, a tributary of the Housatonic watershed. This hike will include a discussion of forest and land use history and connections to river and stream health in the Berkshires. The walk down to the falls follows a switchback trail that is at times steep and then continues on the 1-mile trail to Campbell Falls State Park in CT. Bring hiking poles if needed. 2 hours–2 miles
To register, email— ereardon@hvatoday.org
Meet at the Campbell Falls Road trailhead in New Marlborough, MA (NOT the CT trailhead). From the center of New Marlborough, drive south on New Marlboro-Southfield Rd., which becomes Norfolk Road. After 6 miles, take a right onto Campbell Falls Road OR, From Norfolk, drive north on Rt 272-North St. *Pass the CT trailhead* and drive a bit further to the MA trailhead, to Campbell Falls Road on the left off of what is now Norfolk Road. GPS 42.045503, -73.232159
8 – Sharon, CT 2 PM to 3:30 PM
A BIOGRAPHICAL CEMETERY TOUR OF SHARON, CT
The Sharon Burial Grounds are rife with the stories of the ill-fated and the almost forgotten. On this walk, the Sharon Historical Society will cover the histories of a few of the less-known members of the community and try to bring their stories to the surface. 1.5 hours–1 mile
To register, email – curator@sharonhist.org
In Sharon, at the intersection of the clocktower and Veterans Memorial, head north on Main Street. Turn at Cemetery Road. We will meet at the Sharon Burial Grounds entrance. GPS 41.881654, -73.476641
SUNDAY – SEPT. 7, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
9 – Lenox, MA 10 AM to 12 NOON
LEARN TREE IDENTIFICATION AT KENNEDY PARK
Join naturalist Chelsey Simmons of Berkshire Environmental Action Team (BEAT) for this informative and engaging slow walk, where we will learn key characteristics of commonly encountered trees in Western Massachusetts. The walk will include tips and tricks for recognizing tree species throughout the year, regardless of whether leaves are present. 2 hours–1.5 miles
Limited to 15 participants. To register, email- chelsey@thebeatnews.org
The walk will start at the Kennedy Park Trailhead at the Lenox Commons stores on Rt 7. The trailhead is located at the end of the “Evergreen Trail”, which is a paved road leading to private homes. Please do not drive down the Evergreen Trail road, as there is no parking. Upon entering the Lenox Commons from Rt 7, park in the main parking lot after passing Chocolate Springs Cafe on the right. Walk down Evergreen Trail Road to the end, to the trailhead.
10 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
11 – Lenox, MA 10 AM to 11:30 AM
BEHIND THE SCENES TOUR OF TANGLEWOOD–BOSTON SYMPHONY ORCHESTRA’S SUMMER HOME
Enjoy a tour of the Boston Symphony Orchestra’s summer Tanglewood campus, the Koussevitzky Music Shed, Ozawa Hall, and the Linde Center for Music and Learning. Learn of the interesting historic background of Tanglewood, the BSO and the Tanglewood Music Center. 1.5 hours– <1/2 mile
Starts at the Tanglewood Main Gate. From the Rt 102 & Rt 183 flashing light intersection at the Berkshire Botanical Gardens, drive north on Rt 183 for 4 miles to the Main Gate. OR From Rt 41 in Richmond, across from the fire station, drive 4.5 miles east up Lenox Rd., and over then down Richmond Mt. Rd. Tanglewood is at the bottom of the mountain. Turn left and you will shortly see the Main Gate. OR From Lenox center, drive a couple of miles on West St./Rt 183 to the Main Gate. GPS 42.34924, -73.31084
12 – Salisbury, CT 12 NOON to 1 PM
CANNON AT 20 PACES! THE RISE AND FALL OF THE AMES IRON WORKS
Contrast a shaded walk along a flat trail beside the Housatonic River with the smoky history of the same land. Lou Bucceri, from the Salisbury Association Historical Society, will share the history about the factory and the people that produced the most powerful cannon of the Civil War. Learn how the cannon destroyed no Confederate targets, but only the man and company who created it. 1 hour–0.25 mile
From the Rt 7 & Rt 112 junction in Falls Village–Drive west on Rt 112 to Dugway Road (opposite the Outfield Entrance to Lime Rock Park), turn right and follow Dugway Rd. for 2 miles. At iron bridge, turn left, then immediately turn right onto Housatonic River Rd. Drive 0.5 mile to parking lot for Falls Village Dam boat launch. OR from Rt 44 or Rt 41–Drive east on Rt 112 until you reach the Outfield Entrance to Lime Rock Park, then turn left onto Dugway Road and follow the above highlighted directions. GPS 41.96389, -73.37200 GOOGLE MAP
13 – Great Barrington, MA 1 PM to 2 PM & 2 PM to 3 PM
ENCOUNTERING W.E.B. DU BOIS–NATIONAL HISTORIC LANDMARK TOUR
W.E.B. Du Bois, the great African-American author and civil rights leader, was born and raised in Great Barrington and returned frequently. Join David Glassberg, UMASS History Professor, for an interpretive tour on a level woods trail leading to the foundation of Du Bois’s boyhood home–a National Historic Landmark and the first destination in the U.S. to tell the story of his life and legacy. 1 hour–0.5 mile.
Meet at the Homesite (at 612 So. Egremont Rd), located 2 miles south of Gt. Barrington center. At junction where Rt 7 & Rt 23 split off, take Rt 23 and drive west for ~ 1 mile. GPS 42.17702, -73.39430 GOOGLE MAP
14 – Chester/Becket, MA 1 PM to 3:30 PM
CHESTER AND BECKET RAILROAD – THE GRANITE LINE
Join the Western Mass Hilltown Hikers Group for a walk on mostly flat terrain on a section of the Chester and Becket Railroad. Built in 1896 as a 5.25-mile spur off the Boston & Albany Railroad to deliver granite from the Becket Quarries to the Chester finishing works. Both Chester and Becket issued bond stock in the quarry company to help in building this line because there was money to be made from the “Chester Blue Granite” for monuments and gravestones. This railroad was blasted out of the steep and winding side of the Walker Brook Valley. The first locomotive to run on this line was a wood burner, and eventually was upgraded to a coal burning locomotive. We will see the remains of a wooden trestle still standing on the trail and also learn how this route was used in Chester’s Emery and Granite industry. Optional continuation on the railbed to the Boston and Albany Connector. Donations for the newly conserved Chester Granite Company Finishing Works property are greatly appreciated. Maps and bottled water provided. Well behaved dogs allowed. Wear sturdy footwear. 2.5 hours–1.25 miles
To register per car load, on- https://westernmasshilltownhikers.ticketleap.com or on our website www.hilltownhikers.com
Meet on Hampden Street at the Chester and Becket Trailhead in Chester. From the junction of Rts 20 & 102 in Lee, take Rt. 20 east and drive 18 miles to the Chester/Becket town line, turn right onto Hampden Street to the trailhead. GPS 42.279567, -72.988070
15 – New Marlborough, MA 2 PM to 4 PM
EXPLORING AN ENCHANTED FOREST – THE NEW MARLBORO PRESERVE
Join Tes Reed, naturalist and New Marlborough Land Trust board member, on an interpretive loop through an enchanted forest. Part of the Land Trust’s larger 114-acre New Marlboro Preserve, the loop trail is primarily shaded in a mixed forest and follows Willow Creek and the Umpachenee River with all its twists and turns. Views of the gorge are spectacular! We will share observations about the forest habitat and consider what natural forces have shaped the landscape. 2 hours–1.3 miles
To register, email- nmlandtrust@gmail.com
From the Old Inn on the Green in New Marlborough village, proceed 0.2 miles east on Route 57 and take the right fork onto Route 183, The parking area and trailhead for the preserve are to the right there 100 yards beyond the fork.
SATURDAY – SEPT. 13, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
16 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
17 – Warren, CT 10 AM to 11:30 AM
A WALK THROUGH THE WEST DISTRICT’S MOUNTAIN LAKE PRESERVE AREA
In addition to its historical significance, the Mountain Lake Preserve, also known as the Bible Camp, contains diverse and sensitive natural resources, and is part of a larger system of undeveloped and protected land. The Preserve, combined with the Wyantenock State Forest, Warren Land Trust’s recently acquired Cunningham Nature Preserve, the Kent Land Trust’s East Kent Hamlet Nature Preserve and other adjacent conservation easements, create a contiguous protected block of approximately 1200 acres with an extensive trail system. The property is also home to high quality water resources, including Straits Pond and Glacier Brook, that are vital to protecting the Lake Waramaug watershed and public water supply in the area. This hike with the Warren Land Trust and the Warren Historical Society folks will feature two trails. The Pond Hike (easy difficulty of 0.75 miles) meanders through a meadow to and along the Pond’s edge and over a dam. Hikers may view beaver and waterfowl activity in the swamp, below the dam, and the serene Straits Pond above. The Lookout Hike (moderate difficulty of 1.25 miles) heads into the woods and up to a highpoint on the property with an expansive western view of distant hills. From there, the trail travels down, through an outcropping of massive boulders to arrive at an extraordinary natural amphitheater where campers once gathered for both prayer and entertainment. 1.5 hours–2 miles
To register – www.WarrenCtHistoricalSociety.org/Events
Meet at 64 Mountain Lake Road, Bible Camps. From the center of Warren, drive south on Lake Road and eventually take a right turn onto Curtiss Road. Drive down Curtiss Road until reaching and making a left turn onto Mountain Lake Road, and drive to the end. OR From New Preston, drive north on East Shore Road, passing Lake Waramaug on the left. East Shore Road then becomes Lake Road. After a bit, take a left onto Curtiss Road. Drive down Curtiss Road until reaching and making a left turn onto Mountain Lake Road, and drive to the end.
18 – Sharon, CT 10 AM to 12 NOON
GOODBODY PRESERVE–HIKE INDIAN MOUNTAIN
Join Tim Hunter and the Sharon Land Trust, for a hike on this 188-acre preserve, which offers spectacular views of the Sharon Valley and Indian Lake! Take a deep breath and enjoy the view, as the lands that are seen from this lookout are almost all preserved, either by the Sharon Land Trust or by other regional conservation organizations. Parts of this hike are steep, as the trail gains elevation of 600 feet. For intermediate to advanced hikers. NOTE: Because of the group size, we are asking hikers not to bring their dogs along. 2 hours-–2.5 miles
To register – visit our registration page online, email timhunter@sharonlandtrust.org or call (860) 499-0763
Meet at the trailhead, at 140 Millerton Road (Rt 361), in Sharon (0.6 mile south of Dakin Road). Parking is at the top of a short, but steep, drive up to a farm field parking area. GPS 41.904849, -73.491425
19 – Pittsfield, MA 11 AM to 12 NOON
HISTORY TOUR OF THE GILDED AGE COLONIAL THEATRE
Enjoy a journey through the history of the Colonial Theatre, owned by Berkshire Theatre Group, as you hear the story of the 1903 world-class theatre, movie house, National Historic Treasure appointment by Hillary Clinton, restoration, and 2006 grand re-opening. 1 hour
To register, email- volunteer@berkshiretheatre.org or 413-448-8084 ext 31
Located at 111 South St., in the center of Pittsfield–just north of the junction of Rts 7 & 20 and Ben & Jerry’s. GPS 42.44622, -73.25402
20 – Great Barrington, MA 11 AM to 1 PM
GREAT BARRINGTON’S ARCHITECTURE & HISTORY – THE STORY OF GREAT BUILDINGS IN A GREAT TOWN
This walking tour with Nicholas Greene, from Clark, Green & BEK, will lead participants on a stroll through historic downtown Great Barrington as they discover the rich history of the town’s former and current inhabitants, their lives and the beautiful building architecture they called home. 2 hours–1 mile
To register- greenen23@gmail.com (indicate “GB Architecture Tour & Date” in the subject line). Sign up closes for the tour at 8 PM the night before the Walk
Meet at the engraved stone monument at the corner of Main and Castle Street, Great Barrington, MA. GPS 42.19378, -73.36382 GOOGLE MAP
21 – Stockbridge, MA 11 AM to 12:30 PM
HIKE TO HERMAN MELVILLE’S “ICE GLEN”
Join volunteers from the Berkshire County Historical Society for a leisurely hike to the Ice Glen glacial ravine in Stockbridge, where Melville and Nathaniel Hawthorne walked the same day as they hiked up Monument Mountain. We start at the Stockbridge Town Hall parking lot, walk through Laurel Park, cross the Housatonic River, and then head up into the hills in search of Ice Glen, walking through giant boulder fields and cool ravine scenery! The more adventurous can venture into the boulders and crevices, while others can return for a leisurely walk along the river. Wear good hiking footwear. 1.5 hours–1.5 miles. Raindate Sept. 14 at 11 AM
Meet at the Stockbridge Town Hall parking lot on Main Street/Route 102 which is 0.25 mile to the east of the Red Lion Inn. GPS 51.1142 N, 1.4942 W
22 – Monterey, MA 1 PM to 3 PM
KNOX’S NOBLE TRAIN OF ARTILLERY THROUGH MONTEREY
Join Rob Hoogs, from the Bidwell House Museum and Monterey Historical Society, on a walk in the footsteps of Col. Henry Knox’s Noble Train of Artillery. Pulled by oxen and ice sledges, their winter caravan took 56 days to move 60 tons of artillery consisting of 43 cannons and 16 mortars captured from the British at Fort Ticonderoga and Crown Point on Lake Champlain. They passed through Monterey on Jan. 10, 1776, on their 300-mile trek to Boston to present the cannons to Gen. Washington. The cannons were emplaced on Dorchester Heights and resulted in the British Army evacuating the city on March 17, 1776. We will walk on a section of the old “Great Road” through Monterey, starting at the remains of Chadwick’s Tavern and proceeding westerly along Brett Road. There are several sections of this old road that are relatively unchanged since the 1800s, making it easier to imagine the challenges faced by Col. Knox’s group. NOTE–Does not include a tour of the museum interior. An inside tour, for a fee, can be arranged before or after the free Heritage Walk. Wear sturdy footwear, bring tick repellant & trekking poles if needed. 2 hours–1.5 miles
To register, email – bidwellhouse@gmail.com OR go to the Museum website – Bidwell House Museum
Meet at the Bidwell House Museum and then carpool 2 miles to the start of Walk. From Monterey center–take Tyringham Rd. for 1.5 miles, and take a left onto Art School Rd. and drive 1 mile to the end; OR From the traffic light at Big Y in Lee–take Tyringham Rd and drive 5.5 miles, take a right onto Monterey Rd and drive for 2.3 miles, then take a right on Art School Rd. and drive 1 mile to the end at the Bidwell House Museum. GPS 42.20888, -73.21830
23 – Pittsfield, MA 1 PM to 3 PM
REDISCOVERING THE LOST MILL VILLAGES OF WEST PITTSFIELD – STEARNSVILLE, BARKERVILLE AND THE TILLOTSON OSCEOLA MILL
In the 19th century, virtually the entire economic and social life of the west side of Pittsfield was centered around the Stearns, Barker and Tillotson Mill Villages on the southwest branch of the Housatonic River. The villages provided employment for hundreds of men, women and children and had their own housing, stores, schools, and churches. However, by 1890, most of the mills were closed and today are little known in the Pittsfield community. The tour will begin with a slide presentation at the Berkshire Environmental Action Team (BEAT) Center and will be followed by a level walk to the site of the former Barkerville Mill and also a Shaker building. Participants will receive a copy of an illustrated history of the Mill Villages. 2 hours–1.5 miles
To register, email- gallagherfamily4@myfairpoint.net or call 603-562-5863
Meet at the Berkshire Environmental Action Team (BEAT) Center, 20 Chapel St. From Pittsfield, take West Housatonic St./Rt 20 to a left turn on Lebanon Ave., and after one mile take a left turn on Melbourne Rd., crossing a bridge, then immediate turn right on Chapel St. and the BEAT building is right here. OR From Richmond, driving north on Swamp Road/Barker Road, just past the airport, at the curve right in the road, take a left turn onto Melbourne Rd. Just before the bridge, turn left onto Chapel St., and the BEAT building is right here.
24 – Lenox, MA 1 PM to 2:30 PM
DISCOVERING SOME SECRETS OF KENNEDY PARK
Participants will discover the glorious aspects of the Hotel Aspinwall located, within Kennedy Park, and explore the ruins that were left behind. A quote from one of the early Berkshires brochures stated that “The Hotel Aspinwall is located in Lenox, Massachusetts, a resort renowned the world over as one of the most delightful spots in America. It is in the heart of the famous Berkshire Hills, frequently alluded to as the ‘Alps of America’ and richly deserving of the title. Nature here bestowed her gifts with lavish hands. Man has supplemented her works and turned the place into the most fashionable, exclusive and attractive resort in this country”. Rain will cancel this walk. 1.5 hours–1.5 miles
To Register, email- j4chague@gmail.com or 413.441.9971
Park at the Church On the Hill parking lot or at the entrance to Kennedy Park on Aspinwall Rd in Lenox. Both are on Rt 7A/Main St. in the center of Lenox.
SUNDAY – SEPT. 14, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
25 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
26 – Savoy/Windsor, MA 10 AM to 12:30 PM
BOREAL SPRUCE-FIR FOREST & WATERFALL HIKE – PLANTS, TREES AND WILD EDIBLES AT THE TAMARACK HOLLOW NATURE & CULTURAL CENTER
Experience early fall in the Boreal Forest! Led by Aimee Gelinas, naturalist and director of the Tamarack Hollow Nature and Cultural Center, this hike will feature the unique high elevation flora of the boreal forest, watershed and a waterfall, including tips for tree, plant and wild edible identification and signs of wildlife. Program is free (donations accepted for Tamarack Hollow). This walk has been supported by a grant from the Berkshire Environmental Endowment Fund, a fund of the Berkshire Taconic Community Foundation. 2.5 hours–2+ miles
Registration is Required, email- full_circle_o@yahoo.com
Meet at Tamarack Hollow Nature & Cultural Center, 1515 & 1516 Savoy Hollow Rd, Windsor, MA. Directions can be found at www.tamarackhollow.org on the Donate & Directions page. *Please DO NOT USE a GPS to locate us on Savoy Hollow Road–Only enter Savoy Hollow Road via Griffin Hill Rd off Route 116 in Savoy, MA (you can use a GPS to find Griffin Hill Rd). From Rt 9, in Windsor center, take 8A north to Rt 116 in Savoy. At end of Rt 8A take a right onto Route 116, heading towards Savoy Center and Plainfield. Drive about 1.1 miles through the center of Savoy and take your first right after the center of town onto River Rd (there is a small light brown house with cream trim on the corner, this is #4 River Road). After the small house, cross the bridge over the river and go immediately to your right up the hill – this is Griffin Hill Rd (there is a sign saying “Tamarack Hollow-1 mile”). Continue up Griffin Hill Road (which will become Savoy Hollow Rd) for approx. 1 mile until you reach Tamarack Hollow.
27 – Pittsfield/Hancock, MA 10 AM to 11:30 AM
SHAKERS, NATURE, AND THE CHANGING LANDSCAPE AT HANCOCK SHAKER VILLAGE
Join John Parker at the Hancock Shaker Village for a leisurely walk on the accessible Farm and Forest Trail as we explore the Shakers’ attitudes towards nature and their role in our ever-changing landscape. The walk will touch on geological & glacial history, native plants, birds and other wildlife, Shaker use of natural resources, invasive plants and other human impacts. Participants will learn to interpret clues to “read” changes in the landscape. NOTE: This walk does not include general admission to the Village. For a fee, admission to the Village can be arranged before or after the free Heritage Walk. Wear sturdy footwear. 1.5 hours–1 mile
To register, 413-443-0188 x-213 or cdickinson@hancockshakervillage.org
Meet at the HSV Visitor Center/ticket desk, main entrance, on Rt 20 (34 Lebanon Mt. Road), Pittsfield/Hancock. From the junction of Rt 41 & Rt 20 junction- drive west on Rt 20 for 1/2 mile to the HSV entrance. GPS 42.43091, -73.34049
28 – Stockbridge, MA 10 AM to 11:30 AM and 1 PM to 2:30 PM
A GUIDED WALK OF THE NORMAN ROCKWELL MUSEUM CAMPUS
Join Rich Bradway for a guided walk of the campus of the Norman Rockwell Museum. Explore the culturally and ecologically rich landscape that is now home to the present-day Museum. Walk along the riverbank of the Housatonic and learn about the unique geology and topography of the river and the nearby Oxbow. The walk will also address the site’s beginnings as the ancestral homelands of the Stockbridge Munsee tribe of Mohicans and will trace that history forward from the 18th century farmland era and the 19th century when the Butler family acquired the land and built a grand estate on the property, to the present day as the home of the Norman Rockwell Museum. Rich will also touch on the ongoing efforts of the Stockbridge-Munsee to maintain a connection to their eastern homelands by returning continuously ever since their removal to protect burial sites and other cultural areas and to preserve their connections and heritage. 1.5 hours–0.5 mile
Advance registration required- https://www.nrm.org/events/housatonic-heritage-walk/
From the intersection of Rt 183 and Rt 102 in Stockbridge (at the Berkshire Botanical Garden), drive south on Rt 183/Glendale Rd for 1 mile to the Norman Rockwell Museum. OR driving on Rt 183 from Great Barrington, the Museum is 1 mile before the intersection of Rt 183 and Rt 102 in Stockbridge.
29 – Lee, MA 10 AM to 1 PM
NATURAL HISTORY HIKE ON DONATO’S TRAIL AT GOOSE POND RESERVATION
Bring your walking stick, as Donato’s Trail, a Lee Land Trust property, climbs sharply up a north-facing hillside through a cool hemlock forest. At the top of the ridge, the trail splits into a loop allowing us to explore the ridgeline in Goose Pond Reservation, a parcel held by The Trustees of Reservations. This hike will give you a workout, rising 300 feet, but we’ll make frequent stops, taking time to explore this special place and allow for natural history interpretation. Suggest bringing lunch/snack/drink. Wear sturdy hiking footwear. 3 hours–2.2 miles
Please pre-register, as we need to carpool a bit off site due to limited parking. email- tomnancycondon@gmail.com or phone: 413-454-2331
From the Mass Turnpike/Rt 102/Rt 20 intersection in Lee, drive east on Route 20 (past the Lee Outlets Mall) for 2.5 miles. Look for the sign. The 4 car parking lot is on the right, up a steep incline. Alternative parking instructions will be provided upon pre-registering.
29.b – Norfolk, CT 10 AM to 11:30 AM
A WALKING TOUR OF BARBOUR WOODS
Join forester, Star Childs, on a walk through the Norfolk Land Trust‘s Barbour Woods. No ordinary walk in the woods, Star will talk about the natural surroundings and help identify what sort of activities occurred to shape the forest. 1.5 hours – 1.5 miles
From Rt 44 in Norfolk, turn onto Maple Ave. and continue straight until it turns into Lovers Lane and a dirt road. The trailhead is here. GPS 42.004724, -73.18853
30 – Great Barrington, MA 1 PM to 2:30 PM
THE SEVEN MAUSOLEUMS OF THE MAHAIWE CEMETERY IN GREAT BARRINGTON
This guided tour will feature the history of Great Barrington’s early burial ground and its transformation in the early 1900s into a park-like setting, through the efforts of landscape architect C.T. Barrett of Staten Island. Bernard Drew, from the Great Barrington Historical Society will highlight occupants of carefully placed stone mausoleums (several designed and built by Mathias Lux) and other graves, such as those of civil rights activist W.E.B. DuBois’s family, inventor William Stanley’s family, Civil War Medal of Honor recipient Frederick Deland and others. 1.5 hours–0.25 mile
Meet at the Mahaiwe Cemetery, at the Silver St. entrance, which is off of Rt 7, just south of Ward’s Nursery. The roadway through the cemetery will accommodate autos.
31 – Lanesborough, MA 1 PM to 3 PM
THE HISTORY AND NATURE OF MOUNT GREYLOCK’S SUMMIT – A HISTORIC MOUNTAINTOP WALK
Join Mike Whalen, from the Mass. Dept. of Conservation and Recreation (DCR), and Peter Dudek, from Bascom Lodge, atop Mount Greylock, the most scenic, highest elevation (3,491′) and oldest wilderness state park in Massachusetts. Discover the 1930’s period of great park building when government work programs like the Civilian Conservation Corps (CCC), created special places for recreation. The rustic, yet elegant, “parkitecture” of Bascom Lodge became a distinctive style that defined America’s parks. This is an interpretive walk around the summit of Mount Greylock, with an emphasis on its unique ecology and historic structures as they comprise a fully realized historic landscape; and take an insider’s tour of Bascom Lodge. NOTE–summit parking fee may apply. 2 hours–0.3 mile
To register-413-499-4262 OR email- michael.w.whalen@mass.gov
Meet at the summit of Mt. Greylock in front of Bascom Lodge. Access to the reservation is from Rockwell Rd., off Rt 7 in Lanesborough or from Notch Rd. in No. Adams. GPS 42.636875, -73.16692
32 – Stockbridge, MA 1 PM to 2:30 PM
A PLEASANT STROLL OVER LAUREL HILL PARK AND THE MARY FLYNN TRAIL
Join Patricia Flinn for a leisurely history walk of the Laurel Hill Association‘s signature property, and continuing on to the Mary Flynn Trail. The Association was founded in 1853, and is the oldest existing village improvement society in the U.S. NOTE: Laurel Park is not handicap accessible. However, the second part of the walk on the Mary Flynn Trail is accessible. To join only the handicap accessible Mary Flynn Trail section of this walk, just wait for the group at the end of Park St., which is 2 streets south of the Red Lion Inn, off of Rt 7. 1.5 hours–1.5 miles
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn. GPS 42.28164, -73.30583 GOOGLE MAP
33 – Falls Village, CT 1:30 PM to 2:30 PM
AMERICAN CHESTNUTS – LOST & FOUND
Join Woods Sinclair and friends for a walk and talk in a 2-acre planting American chestnut orchard. Learn of the dramatic sudden loss of this major tree and the ecological impact. Hear of The American Chestnut Foundation‘s efforts to restore this iconic tree to our landscapes. Rain cancels. 1 hour–<0.25 mile
To register–860-824-7454 or fayaway7@gmail.com
From Falls Village, drive north on Route 7. At intersection of Rts 7 and 63, take Barnes Road to its end. Turn right on Under Mountain Road. The orchard is approximately 3 miles on the left, across from 392 Under Mountain Rd. Park on road. GPS 41.94321, -73.28306
34 – Lanesborough, MA 5 PM to 6:30 PM
BOREAL FOREST ECOLOGY SLIDESHOW & SUMMIT WALK AT BASCOM LODGE & MT. GREYLOCK SUMMIT
Learn about the ecology and unique fauna and flora of high elevation Boreal Spruce-Fir forests on a short and easy plant/tree ID summit walk at Mount Greylock, Massachusetts’ highest mountain, and a narrated slideshow in Bascom Lodge with naturalist Aimee Gelinas, director of the Tamarack Hollow Nature & Cultural Center. Program is free (donations accepted). This project has been supported by a grant from the William J. and Margery S. Barrett Fund, a fund of the Berkshire Taconic Community Foundation and supported in part by a grant from the Cultural Council of Northern Berkshire, a local agency which is supported by the Mass Cultural Council, a state agency. For info about Bascom Lodge, visit www.bascomlodge.net. 1.25 hours–minimal walking
Registration is Required, email- full_circle_o@yahoo.com
Meet at Bascom Lodge at the summit of Mount Greylock – the address is 3 Summit Road, Adams. The summit can be reached by taking Rockwell Rd from Lanesborough or Notch Road from North Adams. For more info visit: www.bascomlodge.net and www.mass.gov/locations/mount-greylock-state-reservation GPS 42.636875, -73.16692
SATURDAY – SEPT. 20, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
34-b –bike ride on WNEG in Sheffield ****
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35 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
36 – Otis, MA 10 AM to 2 PM
GUIDED HIKE ON THE KNOX TRAIL IN OTIS
Join the Western Mass Hilltown Hikers on a journey on the original “Ye Trodden Path” to follow the footsteps of the men who saved our country from the British. Narrated by local historian Tom Ragusa, our journey will take us through a section in Otis, stopping at each historical location along the way to hear Tom’s amazing stories. During the winter of 1775-1776 General George Washington held the high ground around Boston while the British were firmly in control of the city. If Washington had artillery, he could dislodge the British and retake Boston. The nearest available artillery was 300 miles away where it had been captured at Fort Ticonderoga, in up-state NY under Continental Army control. General Henry Knox was then commissioned in December 1775, by Washington to secure these 59 cannon and artillery pieces and transport them by way of oxen and sled from NY, through Massachusetts to Dorchester Heights outside Boston. To do this, Knox successfully crossed the Berkshire Mountains and rivers in winter. When the artillery arrived in Boston, 3 months later in March 1776, General Howe realized the hopelessness of his position and the British evacuated the city. Well behaved dogs allowed. More details are on www.hilltownhikers.com 4 hours–3 miles moderate walk, rain or shine
Registration is required. To register per car load, go to https://www.ticketleap.events/events/westernmasshilltownhikers
Park on Norton Street Extension in Otis, near house #92. Take Route 23 to the Center of Otis, then take Norton Road, which is the second road west of the post office. Then bear right onto Norton Road Extension, to the end of the road.
37 – Sharon, CT 10 AM to 12 NOON
HAMLIN PRESERVE – HIKE RED MOUNTAIN
Join Carolyn Klocker, from the Sharon Land Trust, Inc., for a moderate walk along the forest edge to the beautiful upper reaches of Red Mountain. The Hamlin Preserve, protected in 2002, is part of the Red Mountain Trail System, which connects Hamlin Preserve to the Mary Moore Preserve via the Wike Connector Trail. This walk will traverse along ledges and rock outcrops, over streams, and beside vernal pools. NOTE: While leashed dogs are normally allowed on our land trust trails, because of the group size we are asking hikers to keep their pets at home. 2 hours–-2.5 miles
To register – visit our registration page online, or email carolyn@sharonlandtrust.org or call (860) 364-5137
Meet at the trailhead, at 19 Stonehouse Road, Sharon. Stone House Road intersects with Route 41 (Gay Street) approximately 3 miles north of the Town of Sharon. GPS 41.909854, -73.439770
38 – Pittsfield/Hancock, MA 10 AM to 1 PM
SHAKER MOUNTAIN HIKE AT HANCOCK SHAKER VILLAGE
Hike the moderate to strenuous Shaker Trail, located across Rt 20 from Hancock Shaker Village, to the HSV North Family Site and to Mount Sinai, a spiritual “feast ground” for the Shaker community. HSV interpreter Bill Bernbeck will lead this hike, which will include stops at remains of mill sites, the North Family dwelling site (active from 1821-1867), and the summit of the mountain, where the Shakers held special celebratory services twice a year in the mid-19th century. NOTE: This walk does not include general admission to the Village. For a fee, admission to the Village can be arranged after the free Heritage Walk. 3 hours–2.5 mile
To register–413-443-0188 x-213 or cdickinson@hancockshakervillage.org
Meet at the HSV Visitor Center/ticket desk, main entrance, on Rt 20 (34 Lebanon Mt. Road), Pittsfield/Hancock. From the junction of Rt 41 & Rt 20 junction- drive west on Rt 20 for 1/2 mile to the HSV entrance. GPS 42.43091, -73.34049
39 – Becket, MA 11 AM to 1 PM
HIKE TO BASIN POND – A LOOK INTO THE PAST
Join Joe Durwin, from the Berkshire Natural Resources Council, on this hike through BNRC’s beautiful Basin Pond reserve, where he will tell you the story of the natural, human, and social history of this site. Enjoy this hike that traverses streams, big boulders, beautiful wetlands, and a wildlife viewing deck overlooking the pond and former dam, all while learning a story of the folly of man vs. nature. 2 hours–2.5 miles
From Lee–Take Route 20 east past the Outlets Mall and drive 4 miles, then turn left onto Becket Road and drive 1/3 mile to parking area.
40 – Becket, MA 2 PM to 3 PM
93 SEASONS OF JACOB’S PILLOW DANCE FESTIVAL
The buildings and grounds of Jacob’s Pillow have many interesting stories to tell, including Indigenous roots, history as a stop on the Underground Railroad, and championing men dancers in the 1930s. Now recognized as a National Historic Landmark, the site maintains its rustic character while serving as a home for dance artists from throughout the world since 1933. This tour offers an opportunity to gain a behind-the-scenes understanding of why Time Magazine called this secluded spot “the hub and mecca of dancing in North America.” Walk on gravel walkways and dirt paths, rain or shine. 1 hour–0.25 mile
To register online at- jacobspillow.org
Jacob’s Pillow is located at 358 George Carter Road. From Lee, follow Route 20 East for 9 miles into Becket, and then turn left onto George Carter Road. The main entrance to the parking lot will be on your right after 0.75 mile. Meet at the Welcome Center, adjacent to the Ted Shawn Theatre. GPS 42.264087,-73.117888
41 – Sharon, CT 2 PM to 3:30 PM
A BIOGRAPHICAL CEMETERY TOUR OF SHARON
The Sharon Burial Grounds are rife with the stories of the ill-fated and the almost forgotten. On this walk, the Sharon Historical Society will cover the histories of a few of the less-known members of the community and try to bring their stories to the surface. 1.5 hours – 1 mile
To register, email – curator@sharonhist.org
In Sharon, at the intersection of the clocktower and Veterans Memorial, head north on Main Street. Turn at Cemetery Road. We will meet at the Sharon Burial Grounds entrance. GPS 41.881654, -73.476641
42 – West Stockbridge, MA 2 PM to 3 PM
NEIGHBORHOODS OF WEST STOCKBRIDGE – WEST CENTER CHAPEL AND ORIGINAL TOWN CEMETERY
Join Bob Salerno and John Parker, from the West Stockbridge Historical Society, on a tour of the original settlement area of West Stockbridge – site of the first town meeting house and church, then visit the West Center Cemetery where many of our first settlers and Revolutionary war veterans reside. An open air reception will follow at the west Center Chapel. 1 hour–0.5 mile
To register–info@weststockbridgehistory.org
Meet at the West Center Chapel on West Center Road. From Rt 102 / State Line Road, heading west out of the center of West Stockbridge, just after passing Baker St. on the right, take a left turn onto West Center Road, driving around the next bend and continuing left and uphill. Pass Maple Hill Rd. on the left and then pass West Alford Rd on the right. GPS 42.30560, -73.40420
SUNDAY – SEPT. 21, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
43 – Washington, MA Tour any time from 10 AM thru 4 PM
REVISITING CAMP EAGLE (1946 TO 1969) – A BERKSHIRE BOY SCOUT CAMP
Take a walk down memory lane. Visit former Boy Scout Camp Eagle in October Mountain State Forest on Felton Pond, once part of the Berkshire’s vibrant Scouting heritage from 1946 to 1969. Drop-in anytime and discover or reacquaint yourself with various former camp sites. Participants may explore on their own or take a Scout/volunteer-guided tour. View displays on the Scout camp’s history. Participate at an oral history station to record personal memories of camp. Former campers and family are encouraged to bring their own mementoes, photographs, patches, and other ephemera, to be scanned or photographed, to help build a historical archive of former Berkshire Council’s Camp Eagle. Note, restrooms are not available on-site. Wear sturdy footwear, hiking poles, appropriate clothing for the weather, snack/drink. So in fine Scout tradition – Be Prepared! 1.5 hours–less than 1 mile
Parking in October Mountain State Forest is located on Schermerhorn/Lower Tower Road, Washington, MA. FROM Washington: Take Washington Mountain Road to West Branch Road. Take a right on Lenox-Whitney Place Road and then a left on Lower Tower Road. OR FROM Becket, from Route 8, take County Road to Lenox-Whitney Place Road and then a left on Lower Tower Road. OR FROM Lee, GPS: 42°21’36.2″N 73°13’19.4″W
44 – Pittsfield/Dalton, MA 10 AM to 12 NOON
EXPLORE THE FAUNA AND FLORA OF THE BOULDERS PRESERVE
Learn about the plants, trees, wild edibles, tracks and signs of wildlife at The Boulders Preserve with naturalist Aimee Gelinas, director of the Tamarack Hollow Nature and Cultural Center. Program is free (donations accepted). This project is co-sponsored by the Berkshire Natural Resources Council (owners of this preserve) and has been supported in part by a grant from the Dalton Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency. 2 hours–1 to 2 miles
Registration is Required, email- full_circle_o@yahoo.com
The hike will begin at The Boulders’ southern trailhead in Pittsfield. The parking area is at the intersection of Hubbard Ave. and Dalton Ave. (Rt 8/9) at the traffic lights. This is a busy intersection, so please take caution when entering the parking area. Dalton Avenue Trailhead Parking: GPS 42.4701, -73.1961
45 – Lenox, MA 10 AM to 11:30 AM
BEHIND THE SCENES TOUR OF TANGLEWOOD–BOSTON SYMPHONY ORCHESTRA’S SUMMER HOME
Enjoy a tour of the Boston Symphony Orchestra’s summer Tanglewood campus, the Koussevitzky Music Shed, Ozawa Hall, and the Linde Center for Music and Learning. Learn of the interesting historic background of Tanglewood, the BSO and the Tanglewood Music Center. 1.5 hours– <1/2 mile
Starts at the Tanglewood Main Gate. From the Rt 102 & Rt 183 flashing light intersection at the Berkshire Botanical Gardens, drive on Rt 183 north for 4 miles to the Main Gate. OR FROM Rt 41 IN RICHMOND, across from the fire station, drive 4.5 miles east up Lenox Rd., and over then down Richmond Mt. Rd. Tanglewood is at the bottom of the mountain. Turn left and you will shortly see the Main Gate. OR FROM LENOX CENTER, drive a couple of miles on West St./Rt 183 to the Main Gate. GPS 42.34924, -73.31084
46 – Salisbury, CT 12 Noon to 1 PM
CANNON AT 20 PACES! THE RISE AND FALL OF THE AMES IRON WORKS
Contrast a shaded walk along a flat trail beside the Housatonic River with the smoky history of the same land. Lou Bucceri, from the Salisbury Association Historical Society, will share the history about the factory and the people that produced the most powerful cannon of the Civil War. Learn how the cannon destroyed no Confederate targets, but only the man and company who created it. 1 hour–0.25 mile
From the Rt 7 & Rt 112 junction in Falls Village–Drive west on Rt 112 to Dugway Road (opposite the Outfield Entrance to Lime Rock Park), turn right and follow Dugway Rd. for 2 miles. At iron bridge, turn left, then immediately turn right onto Housatonic River Rd. Drive 0.5 mile to parking lot for Falls Village Dam boat launch. OR from Rt 44 or Rt 41–Drive east on Rt 112 until you reach the Outfield Entrance to Lime Rock Park, then turn left onto Dugway Road and follow the above highlighted directions. GPS 41.96389, -73.37200
47 – Stockbridge, MA 1 PM to 2:30 PM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
48 – Washington, CT 1 PM to 2 PM
A STEP BACK IN TIME – TRADITIONAL INDIGENOUS LIFEWAYS IN THE LOWER HOUSATONIC RIVER VALLEY
Join an Institute for American Indian Studies educator as we lead a walk along our museum’s trails and end at our replicated 16th Century Algonkian Village. Get a glimpse into the history and culture of local Weantinock and Pootatuck Tribal people, learn about traditional plant uses, and hear of their community life. Wear sturdy footwear and meet at the front of the museum. NOTE–Does not include a tour of the museum interior. An inside tour, for a fee, can be arranged before or after the free Heritage Walk. 1 hour–0.25 mile
To register–email events@iaismuseum.org or call (860) 868 0518, ext 453
Drive on Rt 67 North through Roxbury and turn right onto Rt 199. Follow Rt 199 North for 2 miles to Curtis Road on left and drive to the end. OR From North Western CT, take Rt 7 South to New Milford and Rt 67. Follow Rt 67 South to Roxbury and turn left onto Rt 199. Follow Rt 199 North for 2 miles to Curtis Road on left and drive to the end. OR From Torrington and Litchfield, Take Rt 202 West towards New Milford. Turn left onto Rt 47. Follow Rt 47 through Washington Depot. Turn right onto Rt 199. Follow for 1-2 miles to Curtis Road on right and drive to the end. Meet at the front of the museum, the last building on the right. GPS 41.61069, -73.32521 GOOGLE MAP
49 – Chester, MA 1 PM to 2:30 PM
THE CHESTER GRANITE AND POLISHING WORKS
The Chester Granite Company was one of two granite finishing works in Chester for cutting and polishing stone brought down to the Historic Factory Village on the Chester and Becket Railroad which was built for this purpose in 1896. “Chester Blue Granite” was brought down the steep mountain railroad from the Hudson and Chester quarry, known today as the Becket Quarry in Becket. The finishing works burned down after many prosperous years in business making monuments and gravestones and has been private property since, until now. In September of 2023, the Hilltown Hikers purchased this lot, including a ten-foot shot saw and all the remains of its buildings and equipment. Join the Western Mass Hilltown Hikers Group for a tour of the property on our newly created walking path and learn about the Granite Industry in Chester and Becket. Several Tours are offered throughout the afternoon. Donations for the conserved Chester Granite and Polishing Works property are greatly appreciated. Maps and bottled water provided. Well behaved dogs allowed. Please wear appropriate footwear. 1.5 hours–1 mile
To register per carload on https://westernmasshilltownhikers.ticketleap.com or under events on our website www.hilltownhikers.comnhikers.com
Meet at the Granite Saw Parking Lot on Emery Street, across from the ballfield. From the junction of Rts 20 & 102 in Lee, take Rt. 20 east and drive 18 miles to Chester center, turn left onto Main Street and bear right onto Prospect Street under the railroad and turn right to continue on Emery Street to the parking lot across from the ballfield. GPS 42.279570, -72.975155
50 – Lenox, MA 2 PM to 3:30 PM
EXPLORE THE FAUNA AND FLORA OF THE PARSONS MARSH RESERVE
On this short, accessible walk, learn about the plants, trees, wild edibles, and signs of wildlife at the Parsons Marsh Reserve with naturalist Aimee Gelinas, director of the Tamarack Hollow Nature and Cultural Center. Program is free (donations accepted for the Cultural Center). This project is co-sponsored by the Berkshire Natural Resources Council, owners of this preserve, and has been supported in part by a grant from the Lenox Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency. 1.5 hours–1.2 miles
Registration is required, email- full_circle_o@yahoo.com
Parsons Marsh Reserve is located at 170 Under Mountain Road. From the center of Lenox, head south on Main St. Turn right at the monument onto Rt 183 south/West St. and follow for 1.4 miles. Turn right onto Under Mountain Rd. The trailhead is 0.9 mile down the road on the right. OR if coming from Stockbridge, from the Rt 102 & Rt 183 flashing light intersection at the Berkshire Botanical Garden, turn right on Rt 183 north and drive for 4 miles to the Tanglewood Main Gate, then turn left onto Under Mountain Rd. The trailhead is 0.9 mile down the road on the right. GPS 42.3644, -73.3049
51 – Lenox, MA 3 PM to 4:30 PM
EXPLORE THE IMPRESSIVE GARDENS & LANDSCAPE OF THE MOUNT – HOME OF EDITH WHARTON
Anne Schuyler will guide you on an exploration of the impressive gardens and woodland trails of The Mount-Edith Wharton’s Estate, a 1902 home (a National Historic Landmark) of Pulitzer Prize-winning author Edith Wharton. NOTE: Does not include an interior house tour, which, for a fee, can be arranged before the free Heritage Walk. 1.5 hours – < 1 mile
From the traffic light junction of Rt 20 & Rt 7 in Lenox, head south on Rt 7, and drive 1 mile, and take a left turn onto Plunkett St. The Mount is right after making the turn. OR if coming from Stockbridge, drive on East St./Rt 7 north, passing Fox Hollow on the right and shortly reach and turn right onto Plunkett St. The Mount is right after making the turn. Meet at the ticket booth. www.EdithWharton.org GPS 42.33558, -73.2829 GOOGLE MAP
SATURDAY – SEPT. 27, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
52 – Stockbridge, MA 10 AM to 11 AM & 1 PM to 2 PM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
53 – Ashley Falls, MA 10 AM to 12 NOON
A GUIDED WALK AROUND HISTORIC ASHLEY FALLS
**photo**
Catherine Miller, from the Sheffield Historical Society, will lead this tour around the Ashley Falls Village Green. Named for the Ashley family who were one of its first settlers, the village has played an important role in the history of Sheffield from its founding. It is the location where the Sheffield Resolves, the precursor to the Declaration of Independence, was written and where Mum Bett lived as a slave. 2 hours – 1 mile
To register- sheffieldhistoricalsociety@gmail.com or 413-229-2694
Meet in front of the Ashley Falls Post Office, at 1180 Ashley Falls Rd./Rt. 7A . From points north and south, take Rt. 7 until you reach Rt. 7A/Ashley Falls Rd. Follow 7A until you reach the Post Office, behind which is a parking lot GPS 42.0563, -73.33561
54 – Great Barrington, MA 11 AM to 1 PM
GREAT BARRINGTON’S ARCHITECTURE & HISTORY – THE STORY OF GREAT BUILDINGS IN A GREAT TOWN
This walking tour with Nicholas Greene, from Clark, Green & BEK, will lead participants on a stroll through historic downtown Great Barrington as they discover the rich history of the town’s former and current inhabitants, their lives and the beautiful building architecture they called home. 2 hours–1 mile
To register- greenen23@gmail.com (indicate “GB Architecture Tour & Date” in the subject line). Sign up closes for the tour at 8 PM the night before the Walk
Meet at the engraved stone monument at the corner of Main and Castle Street, Great Barrington, MA. GPS 42.19378, -73.36382 GOOGLE MAP
55 – Pittsfield, MA 1 PM to 2:30 PM
PLAY BALL ! FIRST INNING – BUT NOT NEAR MY WINDOWS
Join Larry Moore, director of Baseball in the Berkshires and Jim McGrath, Pittsfield’s Natural Resource Program Manager, as they start at “home” at the First Church of Christ on Park Square (23 East St.) where the famous Broken Window by-law was conceived. This tour will follow the “basepaths” around Pittsfield and its historic baseball lore. The walk will take our “players” by the Common – the site of many “All-Star” teams – the Old Elms, the Philadelphia and New York Bloomer Girls and the Brooklyn Royal Giants, then “stealing” up onto Maplewood Ave., where Amherst and Williams College “nines” made history. We will “wind-up” moving back down North St., enjoying some of the architecture of this historic city. 1.5 hours – 1.25 miles
To register – baseballinberkshires@gmail.com or 413-822-6738
Park Square is located at the intersection of North & South Streets and East & West Streets. Meet at The First Church of Christ on the northeast side of Park Square, at 23 East St. Don’t worry about parking meters on Saturdays.
57 – Richmond, MA 1:30 PM to 3:30 PM
TOUR THE NORTHEAST SCHOOLHOUSE AND PART OF THE NORTHEAST DISTRICT
Join Gloria Morse and Bill Edwards, from the Richmond Historical Commission, for an interior view of the historic one room Northeast Schoolhouse, 1791-1937. This is Richmond’s last remaining one room schoolhouse not converted into a home. See the classroom, and photo display of Richmond from the 1930’s. Outside, from the lawn, view part of the Northeast District, remains of the Branch Tavern, and the Cyprian Branch and Linius Hall store and funeral parlor. 2 hours–minimal walking
To register, email- gloriamorse1@gmail.com
Meet at 981 Summit Road which is at the corner of Summit and Swamp Roads. Parking is behind the school, off Osceola Ext. Road. From Richmond – take Rt. 41 to Summit Road. OR From Pittsfield, take Barker Road/ Swamp Rd., just past Bartlett’s Orchard. OR From West Stockbridge, take Swamp Road north to Summit Road.
58 – Pittsfield, MA 3 PM to 4 PM
PLAY BALL! LAST INNING– A TOUR OF WAHCONAH BASEBALL PARK
Join Larry Moore, director of Baseball in the Berkshires and Jim McGrath, Pittsfield’s Natural Resource Program Manager, for “peanuts, popcorn and Cracker Jacks” – a tour of Wahconah Park. Inning 1 participants are encouraged to meet at the Park, where a historic overview of the baseball park will be presented. 1 hour – minimal walking
To register – baseballinberkshires@gmail.com or 413-822-6738
Driving north on North St. from Park Square/the center of Pittsfield, turn left at the Berkshire Medical Center, onto Wahconah Street and then to the park, about 0.25 mile on the left.
SUNDAY – SEPT. 28, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
59 – Stockbridge, MA 9:30 AM to 12 NOON
BULLARD WOODS – A WALK AMONG THE ANCIENTS & SHADOWBROOK ESTATE RUINS AT KRIPALU
Enjoy a hike on a historic gilded age landscape formerly known as the Shadowbrook Estate. The mansion contained 100 rooms and was completed in 1893 for Anson Phelps Stokes, purchased by Andrew Carnegie in 1916, and presently owned by Kripalu Center. Kevin Foran, from the Stockbridge Bowl Association, will take you on a walk through Bullard Woods, an old growth forest, traverse along the north shore of Lake Mahkeenac (Stockbridge Bowl) through Gould Meadows, and loop through the Kripalu/Shadowbrook estate landscape, visiting the remains of the former Shadowbrook/Carnegie home, viewing it’s outstanding stone foundation that is the only thing remaining of the estate. 2.5 hours–2.25 miles
To register, email – moose4an@verizon.net
Meet at the yellow/brown Bullard Woods trailhead sign at the northeast end of Stockbridge Bowl at the junction of West Hawthorne Road & Hawthorne Street. From Lenox center–from the tall marble monument junction, take Old Stockbridge Rd. and take a right onto Hawthorne Street and drive to the intersection with West Hawthorne Road. Or from Rts 102/183 junction in Stockbridge — drive north on Rt 183 for 4 miles to West Hawthorne Rd., take right and drive for 0.6 mile to intersection with Hawthorne St. GPS 42.34446, -73.30601
60 – Becket, MA 10 AM to 12 NOON
EXPLORING THE HISTORIC BECKET QUARRY AND FOREST
Explore The Trustees of Reservations’ historic Becket quarry, with Becket Land Trust founders, Ken and Ann Smith. See industrial archeological remains of this important industry in the area, and how the forest grew up around the site. Learn how the Becket Land Trust saved the property and very nice scenery for nature lovers and historians for generations to come. 2 hours–2.5 miles
From junction of Rts 20 & 102 in Lee, take Rt 20 east and drive about 14 miles, to the junction where Rt 8 turns left off Rt 20–here, you will turn right on Bonny Rigg Hill Rd. Drive about 2 miles and turn left on Quarry Rd. and drive for 1 mile, parking is on the right. GPS 42.25116, -73.02014 GOOGLE MAP
61 – Great Barrington, MA 10 AM to 1 PM
MONUMENT MOUNTAIN HIKE
Join Tony Veilleux, a ranger with The Trustees of Reservations, for a guided hike through Monument Mountain, exploring it’s rich history, diverse wildlife and unique ecological features. This guided hike offers a journey through Monument Mountain’s striking pale quartzite formations and sweeping views of Mount Greylock and the Catskill Mountains. As you explore, you’ll encounter remnants of ancient Native American trails, stone walls from former sheep pastures, historic woods roads, and cart paths once used to transport hemlock bark to tanneries. The Peeskawso Peak Trail, which links the Mohican Monument and Hickey trails, leads to one of the most breathtaking viewpoints in the Berkshires, where you may spot soaring red-tailed hawks and even a nesting peregrine falcon. *Note: Sections of the trail can be strenuous. Wear sturdy hiking footwear. 3 hours–2.5 miles
Pre-registration required, limited capacity. Email- aduquette@thetrustees.org
Meet at Monument Mountain parking lot located off Route 7 in Great Barrington, which is 3 miles south of the Red Lion Inn in Stockbridge or 3 miles north of the intersection of Rts 23 & 7 in Gt. Barrington
62 – Monterey, MA 12 NOON to 2 PM
NATIVE TREE AND SHRUB IDENTIFICATION AND ECOLOGICAL FORESTRY CONCEPTS WITH A LOCAL STATE FORESTER
Explore the woodland trails of the Bidwell House Museum with forester Tom Ryan, from the Mass. Dept. of Conservation & Recreation. Participants are encouraged to ask questions and will learn about tree and shrub identification and ecological forestry concepts such as, carbon sequestration, climate and wildlife habitat adaptive forestry. *NOTE–Does not include a tour of the museum interior, which, for a fee, can be arranged before or after the free Heritage Walk. 2 hours–1.5 miles
To register, email – bidwellhouse@gmail.com or go to website – Bidwell House Museum
Meet at the Bidwell House Museum. From Monterey center–take Tyringham Rd. for 1.5 miles, and take a left onto Art School Rd. and drive 1 mile to the end; OR From the traffic light at Big Y in Lee–take Tyringham Rd and drive 5.5 miles, take a right onto Monterey Rd and drive for 2.3 miles, then take a right on Art School Rd. and drive 1 mile to the end at the Bidwell House Museum. GPS 42.20888, -73.21830 GOOGLE MAP
63 – Sheffield, MA 1 PM to 3 PM
SHEFFIELD AND THE REVOLUTIONARY WAR – A TOUR OF THE BARNARD CEMETERY AND IT’S REVOLUTIONARY WAR SOLDIERS
Listen to the stories of Sheffield’s contribution to the Revolutionary War, as told by their spirits. Participants will engage with actors portraying several Revolutionary soldiers who are buried in the historic Barnard cemetery. Rain or shine.
Pre-register by email- Sheffieldhistoricalsociety@gmail.com
Meet at the Dan Raymond house at 159 Main Street. After a short presentation, participants will then journey to the cemetery on Rt 7 just south of the town.
SATURDAY – OCTOBER 4, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
64 – Lenox, MA 10 AM to 11 AM
NEW ENGLAND MEETING HOUSES, PAST AND PRESENT
Join Lucy Kennedy, from the Friends of the Lenox Meetinghouse and the Lenox Historical Society for a tour of the iconic federalist style meetinghouse, also known as The Church on the Hill in Lenox. Dedicated in 1806, worshippers at the national register property have included early Lenox settlers and Revolutionary War veterans and famous preachers such as Henry Ward Beecher. 1 hour–limited walking
Meet at the Church On the Hill parking lot. Additional parking at the entrance to Kennedy Park on Aspinwall Rd in Lenox. Both are on Rt 7A/Main St. in the center of Lenox.
65 – Stockbridge, MA 10 AM to 11:30 AM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
66 – Washington, MA 10 AM to 12 NOON
THE SECRETS OF MUDDY POND & THE BUILDING OF THE 1ST U.S. RAILROAD MOUNTAIN CROSSING
Dave Pierce, from the Chester Railway Station Museum, offers this hike to Muddy Pond, on the watershed divide of the Berkshires. You will learn of it’s interesting history, as this area presented unique challenges to Whistler’s father as he engineered the world’s first mountain railroad up and over the Berkshire plateau. Hinsdale, MA, is the highest point between Boston and Chicago along the rail line. This area is wonderfully scenic, has abundant wildlife and has an amazing history. Learn why this 5-acre Housatonic River headwaters has earned the title of “most deceptive body of water in Massachusetts.” and the challenges it posed to the first railroad builders over the Berkshires Plateau. This is a level walk on the traprock on the side of the railroad tracks. A tour of the Chester Railway Station Museum, designated a National Historic Landmark in 2021, can be arranged after the free Heritage Walk. Donations for the Railway Station Museum is welcome. Heavy rain will cancel. 2 hours–4 miles
To register–dpiercedlp@aol.com or 413-961-9166
Meet at Summit Hill Rd., and Upper Valley Rd. in Washington. From the junction of Rt 102 & Rt 20 in Lee–Drive 7 miles east on Rt 20 to West Becket, to the junction where Rt 8 splits. Turn left onto Rt 20-east/Rt 8-north. Drive for 5 miles, and at the bottom of a long hill, take a left turn onto Rt 8-north. Drive 10 miles to the Washington Town Hall and take a right turn onto Summit Hill Rd. Shortly, you will reach a narrow bridge over the railroad tracks–park along here. OR FROM DALTON–follow Rt 8 south (approx. 9 miles) and turn left onto Summit Hill Rd. in Washington. Within a short distance, you will reach a narrow bridge over the railroad tracks-park along here. Please don’t park past the bridge on Summit Hill Rd. GPS 42.37490, -73.11129
67 – Colebrook, CT 10 AM to 11:00 AM
THE US ARMY CORPS OF ENGINEERS AND THE CT FLOOD OF 1955
In August of 1955, the eastern US was hit by successive hurricanes. An incredible 25 inches of rain fell in parts of CT, where streams and rivers were unprepared for the deluge. During this tour of the Colebrook River Lake dam, with James Jylkka, we will discuss the worst flood in CT history and the ongoing role of the US Army Corps of Engineers in flood risk management. 1 hour – 1 mile
To register – james.jylkka@usace.army.mil or phone # 860 379-8234
Driving northbound from Rt 44 in Winsted, take Rt 8 north. Approximately 4 miles north of the Shell station, look for the stone pillars on the right, and turn here. Driving southbound from Rt 57, take Rt 8 south. After crossing into CT, you will pass the boat launch. Proceed 1 mile south and look for the stone pillars on the left, and turn here. GPS 41°59’53.2″N 73°02’49.2″W
68 – Lenox, MA 11 AM to 12 NOON
FAMOUS FOREVER RESIDENTS AT THE LENOX HISTORIC CEMETERY
Join Lucy Kennedy, from the Friends of the Lenox Meetinghouse and the Lenox Historical Society for a tour of the Church on the Hill cemetery. The historic cemetery includes memorials to the town’s first settlers, the Walker Judges, and Serge Koussevitsky. 1 hour–0.2 mile
Meet at the Church On the Hill parking lot. Additional parking at the entrance to Kennedy Park on Aspinwall Rd in Lenox. Both are on Rt 7A/Main St. in the center of Lenox.
69 – Great Barrington, MA 11 AM to 1 PM
GREAT BARRINGTON’S ARCHITECTURE & HISTORY – THE STORY OF GREAT BUILDINGS IN A GREAT TOWN
This walking tour with Nicholas Greene, from Clark, Green & BEK, will lead participants on a stroll through historic downtown Great Barrington as they discover the rich history of the town’s former and current inhabitants, their lives and the beautiful building architecture they called home. 2 hours–1 mile
To register- greenen23@gmail.com (indicate “GB Architecture Tour & Date” in the subject line). Sign up closes for the tour at 8 PM the night before the Walk
Meet at the engraved stone monument at the corner of Main and Castle Street, Great Barrington, MA. GPS 42.19378, -73.36382 GOOGLE MAP
70 – South Egremont, MA 11 AM to 12 NOON
THE WORKING LANDSCAPE – EXPLORING APRIL HILL FARM FROM A 1744 FARMSTEAD TO PRESENT DAY EDUCATIONAL FARM AND CONSERVATION CENTER
Join Greenagers‘ executive director, Will Conklin, on a tour through 18th and 19th c. house and farm buildings and a discussion of life and work on the farm from 1744-2025. Also on the tour, the Greenagers educational garden–a 1 acre, hand-scale garden that teaches growing and feeds our community, a community firewood bank, and connections to the Appalachian Trail. 1 hour–0.5 mile
To register–director@greenagers.org or 413-644-9090
Meet at 62 Undermountain Rd., (Rt 41) So. Egremont, MA. From the north: while driving on Rt 23 through the the center of So. Egremont, MA, at the junction of Rt 23 & 41, turn onto Rt 41 and drive 1 mile south. From the south from Salisbury, CT, drive 12 miles north on Rt 41. GPS 42.15456, -73.42070
71 – Great Barrington, MA 1 PM to 3:30 PM
GREAT BARRINGTON AND W. E. B. DUBOIS BLACK HISTORY BIKE RIDE
Join the Du Bois Legacy Committee, Multicultural BRIDGE and the Berkshire Bike Path Council as we explore some of the Black history of Great Barrington. We will start at Mason Library, by the newly installed Du Bois sculpture. This will be a stop and go tour as we visit important sites downtown and further out, including Clinton A.M.E. Zion Church, Five Acres, the W.E.B. Du Bois National Historic Site and others. Please pre-register so that we can predict attendance and to receive a route map. Expect a slow-paced ride, with multiple stops for information and discussion. We will be on public roads. It is possible to follow in vehicles if cycling is not for you. Rain date will be Sunday, Oct. 5 at same time. 2.5 hours–11 miles
To register, email- marjorie.safran@gmail.com
Meet with your bike and helmet at the Mason Public Library, 231 Main St, in the center of Great Barrington.
72 – Falls Village, CT 1 PM to 2:30 PM
HISTORICAL WALK TO THE HOUSATONIC RIVER IN FALLS VILLAGE
Take a guided walk with Judy Jacobs and Bill Beebe, from the Falls Village center to the Falls Village hydro plant & canal system area where historical sites will be viewed and explained. NOTE–An inside tour of the Falls Village-Canaan Historical Society Museum, on Railroad St., is available, for a donation, before or after the free Heritage Walk. (Rain date will be on Sunday, Oct. 5 at 1 PM to 2:30 PM.) 1.5 hours–1.5 miles
Meet at the Falls Village-Canaan Historical Society at 44 Railroad St. GPS 41.953487, -73.364268
73 – Lee, MA 3 PM to 5 PM
WALKING TOUR OF HISTORIC LEE, “GATEWAY TO THE BERKSHIRES”
Join Tracie Etheredge, from the Lee Historical Society, for a walking tour of Main Street, including learning about the important buildings, people and historical events that occurred in town. In the 19th century, Lee was a small but prominent paper making and marble quarrying industrial town. At its peak, the town had 25+ paper mills and several marble quarries, and the town’s prosperity was reflected in its downtown area along Main Street. The town’s first marble quarry opened in 1852 and Lee marble was initially used on a local level; but as demand for the stone in bigger markets grew, larger-scale commercial operations were established. Lee marble found its way into the fabric of major edifices throughout the Northeast and Mid-Atlantic states, including the House and Senate wings of the U.S. Capital, the Boston Public Library, St. Patrick’s Cathedral, Grant’s Tomb, and Philadelphia’s City Hall. The quarries played a significant role in the region’s economy until 1929, when the Great Depression brought the construction industry to a grinding halt, when orders for marble ceased overnight. Another economic backbone for Lee for 200+ years was it’s paper making industry. By the mid-1800’s, Lee, located on the Housatonic River, was the largest paper making town in the U.S. with 25+ paper mills. 2 hours – 1 mile
To register, email – ethere@gmail.com
Meet at the town picnic gazebo next to the post office on Frank Consolati Way. GPS 42.305441, -73.251334
SUNDAY – OCTOBER 5, 2025
PLEASE NOTE–FOR ALL HIKES/OUTDOOR WALKS, PLEASE WEAR HIKING BOOTS/STURDY FOOTWEAR, SUGGEST BRINGING DRINK & SNACK, BUG REPELLENT AND BE PREPARED FOR INCLEMENT WEATHER
74 – Peru, MA 10 AM to 1 PM
EXPLORE THE FAUNA AND FLORA OF THE DOROTHY RICE SANCTUARY
Learn about the plants, trees, wild edibles, tracks and signs of wildlife with naturalist Aimee Gelinas, director of the Tamarack Hollow Nature and Cultural Center. Program is free (donations accepted for the cultural center). This project is co-sponsored by the New England Forestry Foundation and has been supported in part by a grant from the Hinsdale/Peru Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency. 3 hours–2 to 3 miles
Registration is Required, email- full_circle_o@yahoo.com – Visit: http://www.tamarackhollownatureandculturalcenter.org
From the center of Peru, drive south on South Road and meet at the corner of South Road and Rice Road (South Road takes a wide turn at this spot). Rice Road is a grassy lane that leads into the sanctuary. Park and meet at the corner of these two roads.
75 – Stockbridge, MA 10 AM to 12 NOON
SCULPTING THE LAND – DANIEL CHESTER FRENCH’S ARTIST-DESIGNED LANDSCAPE AT CHESTERWOOD HISTORIC SITE
Join Historic Artists’ Homes and Studios program of the National Trust for Historic Preservation, for this walk with Valerie Balint through the various designed landscapes, including the house environs, formal gardens, and woodland walks at Chesterwood. This was the summer home, studio, and gardens of America’s acclaimed sculptor of public monuments, Daniel Chester French, who created 100+ public sculptures. See the design features created by French while living here and place his efforts in the greater context of artist-designed landscapes throughout the country. Participants will go into the studio for a short introduction to this building and how both it and the house relate to the landscape. NOTE – this event does not include a formal tour of the studio or house interiors. An inside tour, for a fee, can be arranged for after the free Heritage Walk. 2 hours–2 miles
Space is limited and pre-registration is required. To register, email- vbalint@savingplaces.org
From Stockbridge center, drive west on Rt 102, turn left on Rt 183. Drive 1/4 mile past the Norman Rockwell Museum and turn right onto Mohawk Lake Road, then left onto Willow St., which becomes Williamsville Rd., just before reaching Chesterwood. Meet at the Barn Gallery. GPS 42.33915, -73.28927
76 – Lenox, MA 10 AM to 11:30 AM
BEHIND THE SCENES TOUR OF TANGLEWOOD – BOSTON SYMPHONY ORCHESTRA’S SUMMER HOME
Enjoy an insider tour of the Boston Symphony Orchestra’s summer Tanglewood campus, the Koussevitzky Music Shed, Ozawa Hall, and the Linde Center for Music and Learning. Learn of the historic background of Tanglewood, the BSO and the Tanglewood Music Center. 1.5 hours– <1/2 mile
Starts at the Tanglewood Main Gate. From the Rt 102 & Rt 183 flashing light, intersection at the Berkshire Botanical Gardens, drive on Rt 183 north for 4 miles to the Main Gate. OR FROM Rt 41 IN RICHMOND, across from the fire station, drive 4.5 miles east up Lenox Rd., and over then down Richmond Mt. Rd. Tanglewood is at the bottom of the mountain. Turn left and you will shortly see the Main Gate. OR FROM LENOX CENTER, drive a couple of miles on West St./Rt 183 to the Main Gate. GPS 42.34924, -73.31084
77 – Lee, MA 11 AM to 12:30 PM
A NATURE WALKING TOUR AT GOLDEN HILL TOWN FOREST
Join naturalist Linda Cysz, from the Lee Land Trust, for a meandering walk through this town forest with huge boulders and colorful fall mushrooms to get a sense of the natural setting and learn some of Lee’s town history. Golden Hill Town Forest’s 70-acre property was once owned by George Westinghouse as part of his estate known as Erskine Park. His house was in Lenox near Laurel Lake and his farmland extended across the road to the Golden Hill area. In 1939 George Westinghouse, Jr. donated this parcel to the Town of Lee. Here is where you’ll find the highest peaks in Lee at about 1220’ elevation. The Pinnacle has views to October Mt., Highlawn Farm and Laurel Lake. This is truly an enchanted geologic world. Easy loop trails guide you through the boulders, ledges, outcrops, wildflowers, mushrooms and old trees. In the early 1960’s this was a vibrant picnic spot with pavilion, stone fireplace and even electricity. Today, that area is an open field. 1.5 hours – 1 mile
Heading north on Rt 20 from the center of Lee, after crossing the railroad tracks and the river, drive for 0.8 mile to Golden Hill Road (across from the Retro Pop Shop). Turn right onto Golden Hill Road and drive uphill for 0.3 mile to a parking site on the right side of road, at Lee Town Forest sign. GPS 42.322441, -73.255433
78 – Great Barrington, MA 1 PM to 4 PM
A GUIDED HIKE TO RESERVOIR ROCKS ON EAST MOUNTAIN IN GREAT BARRINGTON
Join Western Mass Hilltown Hikers Group with special guest Christy Butler, author of Berkshire Destinations and Rockachusetts, for this moderate walking expedition to see an enormous field of boulders, some larger than buses and houses. Huge boulders are everywhere on East Mountain, with many propped up against each other. Footing will be uneven and there will be some elevation gain and walking in between boulders. This area is a mecca for climbers with many challenging and unique bouldering problems that adventurers flock to. The land was purchased from the George Goodrich estate in 1922 by the Great Barrington Fire District. Friendly dogs are welcome, but keep in mind porcupines love rocks too! We will hike rain or shine. Registration required. Please Register per car load on www.hilltownhikers.com Maps and bottled water provided. Wear sturdy footwear. 3 hours–3 miles
From Route 7 in Gt. Barrington, just to the east of the bridge crossing the Housatonic River, and across the road from Berkshire Bike and Board, take East Street, which eventually turns into Pine St. Where Pine St. and Quarry St. intersect, park on the side of the road–please do not block driveways.
79 – Stockbridge, MA 1 PM to 2:30 PM
THE HISTORY OF INDIAN TOWN – STOCKBRIDGE
Indian Town was chartered in 1737 as a mission to the Mohican tribe to teach them English, about Christianity and about English agricultural practices. Recently, the Stockbridge-Munsee community in Wisconsin worked with Housatonic Heritage and other local partners to create a tour of the most important Mohican sites along Main Street in Stockbridge. Trained by a creator of the walking tour, OLLI members will lead participants along to learn about the Mohicans, who lived in what is now Stockbridge for thousands of years, and aspects of their culture which are still present today. Stops include the Carriage Barn at the Mission House, the burial grounds and the site of the 2021 archeological dig for the Mohican meeting house. 1.5 hours–1.5 miles
For more information about the Stockbridge-Munsee Community, click here: https://www.nativeamericantrail.org/stockbridge-walking-tour/
To register with OLLI- https://berkshireolli.org/event-6133152 or call 413-236-2190 or email- olli@berkshirecc.edu
Park in the Stockbridge town offices parking lot at Rt 102/50 Main St., just east of The Red Lion Inn.
80 – Windsor, MA 4:30 PM to 6:30 PM
BOREAL SPRUCE FIR FOREST FULL “HUNTER’S MOON” HIKE AT NOTCHVIEW
Experience an early evening hike in the boreal forest and the full moon rising over Sawmill Field at Notchview Reservation (owned by The Trustees of Reservations). Led by naturalist and director of Tamarack Hollow Nature & Cultural Center, Aimee Gelinas, this hike will feature the unique high elevation flora of the boreal forest, including tips for tree, plant and wild edible identification and signs of wildlife. Program is free (donations accepted). This project has been supported in part by a grant from the Windsor Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency. 2 hours–2 miles
Registration is Required, email- full_circle_o@yahoo.com – Visit: http://www.tamarackhollownatureandculturalcenter.org
From Dalton, follow Rt. 9 east, and drive 1 mile past the Rt. 8A intersection in Windsor, to large parking lot on left. OR From the east (from Northampton area), follow Rt. 9 west for 3.5 miles beyond the Windsor–Cummington town line. Large parking lot on right. Meet at the Budd Visitor Center. For directions visit: www.thetrustees.org
================ THE END OF 2025 HERITAGE WALKS =========