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Autumn Walks With A Purpose: Heritage Walks Weekends

By Shawn Hartley Hancock

becketWhat could be better than a leisurely walk on a crisp autumn day? Not much. Unless it’s dozens of walks, each with a different flavor and distinct point of view, led by an expert. That’s what Housatonic Heritage has planned for its impressive 12th annual Heritage Walks Weekends, which kick off this Saturday and Sunday, September 21 and 22. The walks weekend will be repeated on October 5 and 6 (when there’s likely to be more colorful foliage).

The walks, impressive for their number (60 in all) and their diversity, are free guided tours held throughout Berkshire and Litchfield Counties at historic estate gardens, in notable town districts, along nature and hiking trails, and even at industrial-site ruins, all sponsored by Housatonic Heritage, a local nonprofit with a goal to preserve and celebrate the region’s heritage. (It’s also the nonprofit officially designated by the National Park Service to administer the region as a National Heritage Area.) 

“The communities along the Housatonic River have a shared history of pioneering industries, including iron, paper, and electrical generation,” says Housatonic Heritage Executive Director Dan Bolognani. “They’ve also welcomed writers and artists, and are committed to preserving the scenic landscape and natural resources that comprise this special area,” he says.

This weekend in particular, Housatonic Heritage presents the walks in collaboration with The Cultural Landscape Foundation (TCLF), a national group dedicated to increasing the public’s awareness and understanding of its cultural landscapes, especially those they may pass every day, as part of “What’s Out There Weekend in The Berkshires.” 

golfIf this is all sounding like a spoonful of medicine masquerading as recreation, never fear. TCLF brings golf into the mix (and what is golf if not, as Winston Churchill described, “a good walk spoiled?”),  making tee times available at the Berkshire Hills Country Club, the Country Club of Pittsfield, Cranwell, Greenock Country Club, Stockbridge Golf Club, and Wahconah Country Club. TCLF is also the chief host of a party at Shakespeare & Company on Friday, Sept. 20, to kick off the weekend of walks, beginning with a backstage tour at 5 p.m. 

pumpkinsThe walks themselves, which start on Saturday morning, are designed to appeal to the widest possible audience. “Nature lovers, history enthusiasts, and even those with different levels of physical ability can enjoy them,” Bolognani says. “Some of the walks are hikes, which are pretty strenuous, while others are wheelchair accessible.” To that end, many aren’t actually walks at all. All “events,” whether it’s a canoe trip, mountain hike, or bike ride, are what Bolognani calls, “Gee Whiz Qualified,” meaning folks come away impressed, energized, and educated about an aspect of their community they didn’t know about before.   

“We have historians, educators, authors, environmentalists, and other experts as guides for the walks,” Bolognani says, which include interpretive visits to significant sites along the African American Heritage Trail, as well as an amble through a Native American village in Washington, CT, to the site of a former Algonkian village and discussion of the Pootatuck people.

Participants can join Michael White in a bee-hunt at the Bidwell House Museum to learn how farmers in centuries past searched for and captured honey bees, or bike 14 miles (about 2 hours) with guide Dan McGuiness along the Housatonic River from Falls Village to West Cornwall and back. (Don’t worry, it’s mostly flat and the roads are lightly traveled). 

hancockThe less outdoorsy can take “backstage” tours of The Colonial Theatre and Wahconah Park in Pittsfield, Chesterwood in Stockbridge, and Tanglewood. History buffs can explore the historic hamlets of Cornwall Village, Stockbridge, West Stockbridge, and Lee in tours that illuminate little-known aspects of their pasts. (Hancock Shaker Village at right.) Local historian Bernard Drew will guide visitors to the dark side of Monument Mountain in a 2-1/2-hour hike, while naturalists can learn about the return of the American Chestnut tree through a preserve in Falls Village or join Mass DCR expert Alec Gillman as he puts Bascom Lodge and Mount Greylock into historical context. 

According to Rachel Fletcher, a conservationist whose commitment to cleaning up the Housatonic River goes back decades, “We are in a unique position to show the public how central the river is to our community.” Fletcher will lead sessions at Great Barrington’s two Riverwalk parks on Saturday. “It’s the only reclaimed landscape among all the walks,” she says, “and allows us to tell two different and distinct stories.” 

housatonicAlong the upstream area, inventor and entrepreneur William Stanley developed alternating current, forever imprinting the river as significant as an industrial site. Downstream, the W.E.B. Du Bois Park, just a few feet from the abolitionist’s birthplace, reminds visitors of the region’s cultural diversity. According to Fletcher, Du Bois “writes about being ‘born by a golden river’ and was a fierce and longtime river advocate who urged its care and clean-up throughout his lifetime, well into the 1930s.”

mary flynnDu Bois would be happy to know that, in fact, the river was the object of a voluntary effort that removed 400 tons of debris from its shores and its bed over the last 25 years. Today, the half-mile trail through downtown Great Barrington respects nature and reveals the river’s beauty. Other walks that explore the Housatonic will be held at the mile-long Mary Flynn Trail in Stockbridge, and the three-mile-long Old Mill Trail in Dalton. 

The Upper Housatonic Valley National Heritage Area, the local management entity that has partnered with the National Park Service to help educate the public about the Heritage Area, runs from Kent, CT to Lanesborough, MA, and encompasses 29 towns and cities through the hilly terrain of western Massachusetts and northwestern Connecticut.

Many of the walks require pre-registration. For more information, a schedule and description, visit

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