05/06/2026
THE BERKSHIRES! TRAVEL 2026 with Taste of Schenectady® and Beyond™ / Taste and Shop™ magazine, and Home & Towne Travel: Beyond its celebrated arts scene, the Berkshires has quietly become one of New England’s most satisfying culinary destinations. Whether you prefer an afternoon stroll through Hancock Shaker Village, Chesterwood, the fascinating estate, gardens, museum and former studio of Lincoln Monument Sculptor Daniel Chester French, Ella May's Ice Cream, farm wineries, hiking trails, Canna Provisions, attending scheduled classes at Kripalu Yoga Retreat Center, a day spa treatment, a lively night out, or shopping and a quiet evening cooking at your home away from home, the region delivers ALL with ease.
https://www.youtube.com/watch?v=aFgtREkxCQw
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Tucked into the rolling hills of the Berkshires, Western Massachusetts offers a blend of cultural sophistication and rural beauty that’s hard to match anywhere in the Northeast.
One of the region’s most exciting cultural revivals is the Adams Theater in the town of Adams. This reimagined historic space has quickly become a hub for innovative performances, bringing new energy to the northern Berkshires. Not far away, other entertainment places continue to anchor the area’s performing arts scene, staging everything from classic plays to contemporary productions across its multiple venues.
Opera lovers will find something truly special at the Berkshire Opera Festival, where intimate, high-quality productions showcase both emerging and established talent. There are two upcoming performances, Lucia di Lammermoor at the Mahaiwe in Great Barrington, MA (Aug. 22, 25, & 28), and Zémire et Azor at the PS21: Center for Contemporary Performance in Chatham, NY (July 31 and Aug 2).
Meanwhile, in downtown Pittsfield, The Colonial Theatre has been beautifully restored by the Berkshire Theatre Group. It stands as a testament to the Berkshires’ commitment to preserving its cultural heritage while keeping the arts vibrant and accessible. Friday night, May 1, 2026, we attended ‘I’m Going to Graceland,’ a concert by Rev Tor & Friends, featuring special guests Belle of The Fall as "Simon & Girlfunkel". Rev Tor & Friends are an 11-piece band that performed a multicultural and spectacular concert for the 40th anniversary celebration of Paul Simon’s Graceland. Visit the Berkshires of Western Massachusetts, .
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Art enthusiasts should not miss The Clark Art Institute in Williamstown. Set against a backdrop of serene landscapes, the Clark pairs world-class exhibitions with tranquil walking paths, making it as much an experience as a destination. It’s a place where you can spend a full day moving between galleries and nature without feeling rushed.
When it comes to iconic New England hospitality, few places rival The Red Lion Inn in Stockbridge. This landmark property has been welcoming travelers for centuries, offering a quintessential Berkshires stay. Downstairs, the lively The Lion's Den delivers a more casual vibe, with hearty food, craft drinks, and live music that draws both locals and visitors alike. It’s the kind of place where a quiet dinner can easily turn into a memorable night out.
Of course, no Berkshires getaway is complete without a visit to Tanglewood, the summer home of the Boston Symphony Orchestra. Each season, Tanglewood hosts an impressive lineup of concerts, from classical masterworks to contemporary performances. Whether you’re seated in the Koussevitzky Music Shed or enjoying a picnic on the lawn, the experience is nothing short of fabulous—music drifting through the warm evening air as the sun sets over the hills.
What makes the Berkshires stand out isn’t just the individual attractions—it’s how seamlessly they come together. You can spend your morning hiking or antiquing, your afternoon immersed in art, and your evening enjoying theater or live music, all within a short drive.
If you’re looking for a destination that balances relaxation with cultural richness, the Berkshires deliver without trying too hard. It’s not flashy. It doesn’t need to be. The appeal here is deeper, rooted in tradition, creativity, and a landscape that invites you to slow down and actually enjoy what’s in front of you.
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Downtown Pittsfield, Inc. has undergone a genuine revival, with restaurants and cafés lining North Street and surrounding blocks. Here, you’ll find everything from upscale American fare to globally inspired cuisine. It’s the kind of place where dinner and a show isn’t a cliché—it’s simply how the evening unfolds. A short drive away, Lenox offers a more refined, small-town charm with elegant dining rooms and cozy bistros, while nearby, the Lee Chamber of Commerce blends casual eateries with farm-to-table sensibilities that reflect the region’s agricultural roots.
We often eat at La Fogata Colombian Restaurant or sometimes drive a short distance from La Fogata to go out late at night for the fantastic mini weiners at Teo's Hot Dogs in Little Italy, located at 1410 East St, Pittsfield, MA 01201. Teo's Hot Dogs in Pittsfield, MA, opened in 1969. Founded by Tio Bilia and his wife Bertha, this iconic Berkshire County spot is famous for its 4-inch mini hot dogs, commonly served with mustard, onions, and meat sauce.
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But here’s where the Berkshires really separate themselves: you don’t have to dine out every night to eat well. In fact, some of the best meals happen in your own kitchen—especially if you’re staying at a local Airbnb or one of the area’s charming inns.
A must-stop for anyone who enjoys cooking is Guidos Fresh Marketplace. This beloved, family-founded marketplace has been a Berkshire staple since 1979, evolving from a roadside produce stand into a full-scale gourmet food destination. Inside, you’ll find an old-world style food hall with specialty vendors, including butcher-quality meats, fresh seafood, artisanal cheeses, baked goods, and an impressive selection of prepared foods.
WE SHOP HERE FOR ARTISAN AND IMPORTED CHEESES, ORGANIC AND FRESH PRODUCE, HAND-CRAFTED MEATS, COLD SMOKED PASTRAMI SALMON SLICES, AND SALADS!
Guido’s is particularly known for its abundance of organic produce and locally sourced ingredients, along with ready-to-eat options like sandwiches, sushi, and hot bar selections if you want something quick but high quality. It’s not just a grocery store—it’s part of the Berkshires experience, giving visitors access to the same ingredients local chefs rely on.
For more traditional grocery needs, Price Chopper Supermarkets offers a convenient, well-stocked selection of pantry staples, fresh meats, and produce. Pair that with a visit to one of the many roadside farmstands scattered throughout the region, where you can pick up just-harvested vegetables, fresh eggs, maple products, and seasonal specialties.
Diverse restaurant dining paired with high-quality local shopping makes the Berkshires ideal for longer stays. You can enjoy a late night out in Lenox at Ombra until 1:00 a.m., spend the next evening making Creole Salmon Rundown and Sausage & Seafood Jambalaya, as we did, grilling steaks or preparing a farm-fresh meal at your Airbnb, and still feel like you’re indulging.
That’s the real rhythm of the Berkshires: culture and history by day, music or stage theater by night, and in between, some of the best food and shopping experiences—both out and at home—you’ll find anywhere in New England.
Check out the Festival Latino of the Berkshires, the Visit Lenox 45th Annual Apple Squeeze Festival, Norman Rockwell Museum, Homelands PowWow (October 3-4, 2026), and Visit the Berkshires of Western Massachusetts this season!
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BERKSHIRE TRAVEL 2026 with Taste of Schenectady® and Beyond™ / Taste and Shop™, and Home & Towne Travel: Beyond its celebrated arts scene, the Berkshires has...
