If there is one time of year to bolt out of Gotham to explore happenings among the artsy towns throughout western Massachusetts, it is during the fall season. Once all glitz and glamour, the Berkshires played host to the east coast elite during the Gilded Age and simultaneously became a hub for various industries, from paper (Crane & Co. is still located in Dalton, MA) to energy and textiles. Anchored by the arrival of Berkshire Theatre Festival (1928) Jacob’s Pillow, (1931) and Tanglewood (1937), the area has become known for its cultural impact, and more recently, its leading role in the farm-to-table movement.
Where to Sleep
The Topia Inn($150-$260/night) is possibly the greenest and quaintest bed & breakfast you can find in the Berkshires—featuring organic beds and linens, American clay earth plaster, IceStone recycled glass countertops and renewables such as solar panels, biodiesel fuel and sustainable wood. Conceived by co-owners Nana Simopoulos and Caryn Heilman with contributions from an array of artists and builders, this eco-friendly sanctuary is nestled in the sleepy town of Adams with easy access to the Ashuwillticook Trail. The inn offers bike rentals for $20/day, so consider riding off on the historic 11-mile path, which showcases several Berkshire County communities and beautiful scenic vistas. Once settled in, take advantage of an aromatherapy rain shower or chromatherapy bath and array of complimentary organic bath products.
Where to See Art + Culture
There are a wide range of activities that capture the locavore culture and rich historical traditions of the Berkshires. Hancock Shaker Village ($17 admission) is a historical landmark, comprised of 18 buildings and more than 22,000 objects exemplifying the original “green” movement. In nearby Stockbridge is the Norman Rockwell Museum ($15 admission), celebrating the iconic work of a master illustrator and portrait artist.
Local Intel:
Castle Street Cafe: Featuring live music on the weekends and a surprising wine list. Mass MoCA: Currently showcasing the work of Sol LeWitt. Check out our guide to North Adams, home of the museum. Rubiner’s Cheesemongers & Grocers: So good they don’t even have a website. Bascom Lodge: Rustic accommodations at the top of Mount Greylock. |
For contemporary inspiration, head to Pittsfield, the epicenter of the Berkshires. The city’s Office of Cultural Development is steadily cultivating its pool of visual, performing and literary artists. Visit the Berkshire Museum ($15 admission), the Ferrin Gallery, or for a taste of something truly dramatic, Barrington Stage Company ($15-$35 tickets).
Where to Eat
If you’re craving something meatier than onstage drama, the Berkshires food culture does not disappoint. Berkshire Grown is a community-driven organization that promotes local food, farming and culture, and has created a database of more than sixty member restaurants. Must-eats include Route 7 Grill—restaurateur Lester Blumenthal’s homage to barbecue—featuring an array of smoked meats, local produce and delicious local libations from Berkshire Mountain Distillers including a New England corn whiskey. Also not to be missed is Mezze Bistro + Bar, a special occasion restaurant that sits just outside of Williamstown overlooking Sheep Hill. Future plans include edible gardens, sustainable landscaping, and architecture, but for the time being guests will have to be satisfied with the impeccable locally sourced creations of Chef Joji Sumi, including Boston mackerel escabèche, heirloom bean and vegetable ragout, or house-made tagliatelle with braised Cricket Creek Farm veal.
Where to Enjoy the Great Outdoors
No fall trip to the Berkshires would be complete without an outdoor adventure. The Berkshire Scenic Railway offers a 90-minute roundtrip excursion between Lenox and Stockbridge, capturing the region’s rich industrial traditions and natural scenic beauty along the Housatonic River. And for a final stop before heading back to the concrete jungle, be sure to visit Hilltop Orchards, a family-run 200-acre property offering apple picking, guided bike rides, hay rides, and a new hiking trail designed by seven-time Olympian John Morton ($5 entrance fee with a portion of proceeds donated to land preservation).
Whether you are a leaf peeper, art enthusiast, foodie fanatic or outdoor adventurer, the Berkshires offers city-dwellers one of the most diverse range of activities in the Northeast.
How to get there: From Port Authority in midtown Manhattan, hop on the Peter Pan bus to the Great Barrington stop in Massachusetts. The trip will take under 4 hours and depending on the days of travel, cost $85 roundtrip. Use the Berkshire Regional Transport Authority bus system to get around town once you’re there , or consult oM’s Guide to Renting Hybrids in NYC. For those interested in covering a lot of ground on a weekend getaway, renting a car (preferably a hybrid!) is advised.
Photos in order: Courtesy of the author, Hancock Shaker Village, Jennifer Mardus, and Ovondrak
Map of Things to Do in the Berkshires
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Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram