‘Tis the season for the Berkshires to turn into an irresistible mix of cozy inns, world-class art, and outdoor adventure. Spend a weekend discovering quintessential New England villages, contemporary art spaces, local restaurants, and outdoor recreation for all ages and abilities. The Berkshires is a perfect four-season destination with plenty of ways to take in the crisp mountain air, all within easy drives between charming towns across the county.
Historic: The Berkshires has been an escape from the hustle and bustle of everyday life for centuries. Plan a visit to one of these iconic historic house museums and get a glimpse into the lives of literary and artistic legends. Plus, you’ll find unique seasonal events throughout the year that bring these pastoral landscapes to life. Don’t miss the Gilded Age flair of Naumkeag; Chesterwood, the Berkshires home and studio of renowned sculptor Daniel Chester French; Edith Wharton’s, The Mount, highlights her career as a writer and designer; and Arrowhead, the home of Herman Melville.
Outdoorsy: You’ll find four seasons of outdoor adventure in the Berkshires including snowmobiling, skiing, tubing, biking, golf, hiking, and more. Don’t miss out on your chance for some intriguing wildlife viewing or bird watching across the region. Take your chances of seeing rare species at wildlife sanctuaries or tracking animals like deer, porcupine, or rabbits on a hike.
Hidden Gem: Discover the Berkshire Botanical Garden in Stockbridge where you’ll find year-round ways to engage with the flora and art of the region as well as educational programs and advice to get your own garden growing beautifully. Don’t forget to check out the new statute in Great Barrington of W.E.B. Du Bois. Did you know his roots are in the Berkshires?
Craft Beverage: The Berkshires’ craft beverage scene is robust and lively! Berkshire Mountain Distillers in Sheffield has been crafting award-winning artisanal spirits for nearly two decades. In New Marlborough, you’ll find Les Trois Emme Winery – a family-owned vineyard and wine experience, still in the mood for more wine, then be sure to visit Balderdash Cellars in Richmond. Hot Plate Brewing Co. in Pittsfield is an award-winning, Latina-owned brewery and taproom on a mission to make the craft beer world more inclusive. Take a hike or enjoy snowshoeing then check out the offerings at JMash Cidery at Hilltop Orchards in Richmond.
Unique Shopping: Across the Berkshires communities you’ll find a wide array of shopping experiences ranging from thrift and secondhand shops like Catwalk Boutique in Great Barrington or independent bookstores like Indie Readery in Pittsfield; In Lenox, take a walk around Church and Main Streets and explore the upscale boutiques, galleries, and bakeries. A visit to The Magic Fluke Shop in Sheffield offers an inside look at how these instruments are made, is an educational and fun stop for music lovers of all ages. Don’t miss ROAM in Williamstown where ethical design meets exquisite storytelling.
Museum and Performing Arts: MASS MoCA in North Adams is a must for contemporary art lovers — enormous, daring exhibitions and performances run year-round and make for a memorable, often indoor-friendly winter visit. The Norman Rockwell Museum in Stockbridge introduces visitors to the artist’s iconic work and seasonal exhibits. Jacob’s Pillow brings a ‘hub and mecca of dancing’ to Becket and is America’s longest-running international dance festival. It wouldn’t be summer without a trip to Tanglewood to experience the summer home of the Boston Symphony Orchestra.
Family Friendly: For families, Jiminy Peak Mountain Resort in Hancock offers a year-round outdoor adventure experience that features a three-season Alpine Slide and ziplining as well as winter skiing and riding. The Clark offers a wide range of ways that families can engage with art and the museum. If your family loves a challenging hike with a big reward, check out Bish Bash Falls in Mt. Washington.
General Store Stop: Pop into Williams & Sons Country Store in Stockbridge is a classic general store experience. You’ll find old-time candies, local provisions, and Berkshires souvenirs. It’s the kind of place to pick up a cozy knit hat or a jar of local preserves before you head up into the hills. Or stop in Lanesborough Local where you can find a little of everything here from local handmade gifts, nostalgic toys, farm fresh ice cream, groceries, beer, wine and baked goods.
Roadside Attraction: TurnPark Art Space in West Stockbridge is a marble quarry turned sculpture park. You’ll find stunning views of the Berkshires and art installations like no other in Massachusetts.
Seasonal Highlight: The Berkshires are home to more than half of Massachusetts’ independently owned ski areas. Besides traditional winter sports, you’ll find year-round fun at many of these ski areas including music festivals, culinary events, and outdoor adventure sports.
Where to stay
Budget: The Blue Vista Motor Lodge in Florida is convenient, comfortable, and wallet-friendly. This is an ideal for all that the Berkshires has to offer, including snowmobiling in the winter season. Plus, the views are some of the best!
Boutique: Doctor Sax House is located in the heart of Lenox. This 1874 building has been lovingly restored with stylish and comfortable guest rooms, an art deco inspired cocktail and bar experience, and fantastic food offerings.
Luxury: The Williams Inn in Williamstown offers easy access to all that the Northern Berkshires has to offer while bringing the outdoors into the 64 locally-inspired contemporary rooms.
Memorable Meals and Local Flavor
You’ll find comfort classics throughout the Berkshires but it’s also a region of Massachusetts where you can explore global flavors. MINT Lakeside Dining in Lee is a renowned Indian restaurant with unparalleled water views in the region. Mazzeo’s Ristorante in Pittsfield serves up Italian classics and homemade pasta. Casita offers up authentic Mexican cuisine and experiences in North Adams. Looking to have a fine dining experience by candlelight? Be sure to check out Old Inn on the Green. For a taste of Naples be sure to stop in Pizzeria Boema and try out their wood oven pizza.
Picture Perfect Stop
Monument Mountain provides a striking backdrop for the perfect photo moment. You’ll find lots of natural drama when you hike the Peeskawso Peak Trail. This challenging trail traces the rocky ridgeline and offers a vista of the iconic Devil’s Pulpit. Also home to the tallest mountain in MA, be sure to make a stop at Mount Greylock when the weather permits.
Ready to plan your trip?
Whether you’re chasing lights and holiday markets or carving fresh tracks on the slopes, the Berkshires blend culture and landscape for an unforgettable overnight escape. Start building your Berkshires winter getaway.
