So Much to Do in Berkshire County
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Massachusetts is famed for its colorful foliage — especially Berkshire County — but there’s more to do in this Western Mass. enclave than merely leaf-peep. From savoring seasonal goodies like apple-pie ice cream to navigating forest adventure trails or a corn maze, here’s how you can experience the treetops and not just admire them while driving by.
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Sip and savor
Before you hit the road for a day of hiking, there’s no better place to caffeinate than Fuel Cafe on Main Street in Great Barrington. Offering breakfast on the weekends, a selection of tasty gluten-free baked goods, and sandwiches like the fried-egg McGuido — a favorite among locals that also includes a Berkshires-roasted coffee — it’s good for grab ‘n’ go, unless you’re lucky enough to snag one of several small tables.
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Talk shop
Pop into boutiques on Railroad Street in downtown Great Barrington to amp up your fall wardrobe or browse home curios. Church Street Trading Company offers upscale labels for men and women; find fun toys and clothes at the Gifted Child; or get the newest home gadget at The Chef’s Shop. GB9 boutique is the latest addition to the street’s trend-setting lineup.
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Go ‘apple picking’
Mexicali Chocolate and Mission Fig are among the most popular in the year-round lineup, but fall has some of the tastiest limited-edition flavors at SoCo Creamery . The rotation includes pumpkin, and apple pie, each made in microbatches in the heart of Great Barrington for 25 years.
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Bookmark it
Need a good read? The Book Loft , an independent bookseller since 1974, has a recommendation. Featuring friendly service and themed tables geared toward various interests —travel, Berkshires landscapes, sports — each staff member keeps a regular blog so you can compare your favorites and outside-the-box picks.
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Fall on the Farm
There’s no better time than autumn to check out what’s fresh from the fields at Taft Farm, family owned for four generations. Featuring a corn maze, pick-your-own pumpkins, and hayrides through the end of October, there are also animals so kids can experience a working farm, and the store features farmhouse kitchen fare and local produce, all chemical- and pesticide-free.
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Feast for the eyes
For creative cocktails, or a fun afternoon peering at colorful swag as you try to figure out what’s in their secret “yuni’’ sauce, check out the extensive menu at Gypsy Joynt Cafe. The family-owned business on Main Street in Great Barrington has branched out into a clothing company, and Jive, an arcade. Pick up delectable baked goods, including massive cinnamon rolls, to win friends back at the office on Monday.
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View from the top
Enjoy views as far as Mount Greylock to the Catskills of New York and the Housatonic River Valley below from Monument Mountain trails. There are several loop options, each no longer than 3 miles total; the sweat you work up ascending them is worth it for the autumn panoramas.
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Zip drive
Ramblewild, a new “tree-to-tree’’ adventure outfit, takes one of the area’s most popular fall activities — zip-lining — up a notch by combining it with ropes courses through 900 acres of Berkshire woods in Lanesborough. Eight “trails’’ offer varying level of heart-thumping and laughter-inducing challenges, appropriate for children and adults.
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Raise a glass
Fall Sundays mean it’s time for football, and there’s no place better to watch than Moe’s Tavern — just don’t expect a watered-down draft. Here you’ll find only American craft brews. It’s BYOF (bring your own food), and locals can be seen siding up to the bar with takeout from Pho Saigon across the street. Decide to watch the game at home? Pick up a six-pack at Trader Moe’s store.
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See what’s ‘in store’
A babbling brook flows through trees with turning leaves behind Monterey General Store, where most weekend visitors elect to nibble and read the newspaper, but this is far from “Little House on the Prairie’’ fare: expect upscale sandwiches like pate with cornichons served with a side of organic greens.
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Bon appetit
Most dining in the Berkshires is casual, even if the fare is upscale — and Chez Nous in Lee is no exception (though the fare is exceptional). Advance reservations are suggested, especially during peak foliage season. Each experience is different because the menu changes daily, and one recent evening featured a peach dessert with fruit from a server’s backyard. Try one of their generous half-portions of main dishes.
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Chasing waterfalls
Enjoy a clear view across Massachusetts into New York State from the summit atop Bash Bish Falls in the Taconic Mountains. The highest waterfall in Massachusetts, you can take a pleasant hike by starting the trail on the New York side (Route 344), or skip straight to the “high points’’ and enter through Massachusetts’ Falls Road.
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Rooms with a view
The vistas on the drive leading to Bascom Lodge are worth it alone, nevermind the reasonably priced breakfasts and lunches, or more upscale three-course dinners with produce from local farms. Adventure-seekers — mountain bikers, hikers, and snow-shoers — flock to the accommodations and trails here (including a stretch of the Appalachian) year-round.
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‘About Face’
Housed in a former church in South Lee, St. Francis Gallery offers unique perspectives both inside and out. Light streaming in from stained-glass windows adds a unique perspective to each new exhibit, and the latest, which runs through October 19, focuses on the face and creative expressions.

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