Where to Get Off the Beaten Path in the Berkshires

The Berkshires is more than just Tanglewood and MASS MoCA. Here are eight under-the-radar spots to explore.

Where to Get Off the Beaten Path in the Berkshires

Shaker Dam Coffeehouse & Stanmeyer Gallery

Photo by John Stanmeyer

The mountainous area of Western Massachusetts known as the Berkshires is one of those magical places that’s gorgeous any time of year, and is chock-full of nature excursions, cultural activities, and superb food and drink. While places like Tanglewood and MASS MoCA tend to get all the glory (and for good reason—they’re awesome), there are also countless under-the-radar spots that are worth exploring. Here are eight of them.

1. Ashuwillticook Rail Trail


Photo by essygie/Flickr

Originally a railway line built in the mid-nineteenth century, the Ashuwillticook Rail Trail came about when train service stopped in the 1990s and local residents petitioned to turn the space into a recreational trail. Traversing 11.2 miles from Lanesborough to North Adams, the paved path runs through the mountains and along the Cheshire Reservoir and Hoosic River, which makes for some pretty spectacular views. In the warmer months it’s the perfect place for biking, rollerblading, running, and walking, while it becomes a nice spot for cross-country skiing and snowshoeing come winter. There are restrooms along the way and even a pub (CJ’s) in the old Adams railway station right on the path. —Between the Lanesborough Mall and the Adams Visitor Center along Rt. 8 | website2. Chocolate Springs


Photo courtesy Chocolate Springs

For a sweet reprieve, a stop at Chocolate Springs is a must. Owner and chocolatier Joshua Needleman is Culinary Institute of America–trained and put in his time at places like La Maison du Chocolat in Manhattan and Paris before opening up his own chocolate shop and cafe in Lenox. Needleman is obsessive in the best way possible, creating impeccable chocolates with flavors like kalamansi, lavender honey, and rose tea. The cakes, cookies, gelato, coffee, and of course hot chocolate are worth sampling as well. The welcoming cafe is open daily from early to late, and often has live music. —55 Pittsfield Lenox Rd., Lenox Commons | (413) 637-9820 | website3. The Eric Carle Museum of Picture Book Art


Photo by Seth Kaye Photography © The Eric Carle Museum of Picture Book Art

If you’re one of the countless people who grew up reading Eric Carle books (or reading them to your children), then this gem of a museum is not to be missed. Started by the author and his late wife, the museum celebrates picture books from around the world, both as works of art and educational tools. Located next to Hampshire College in Amherst, they have an impressive permanent collection as well as rotating special exhibits like The Art of Eric Carle: From A to Z and Alice Is...A Celebration of Alice’s Adventures in Wonderland. They also host an array of events, like The Very Hungry Caterpillar Day in March and the Children’s Book Festival in June. —125 West Bay Rd., Amherst | (413) 658-1100 | website4. Bascom Lodge


Photo courtesy Bascom Lodge

At 3,491 feet, Mount Greylock is the highest point in Massachusetts and became the state’s first wilderness state park in 1898. The 12,500-acre reserve, which is a favorite for multi-season hiking and recreation, is no secret, but what many don’t know is that Bascom Lodge, which sits at the top, offers seasonal accommodations and world-class meals with a breathtaking view. Whether you drive to the top or need to rest after a long hike, the rustic 1930s stone lodge is a welcome sight. The lodging is basic but quite comfortable and the menu, masterminded by Manhattan-trained chef John Dudek, is locally sourced and changes daily depending on what’s in season. —Open July to October | (413) 743-1591 | website5. Notchview


Photo courtesy Notchview

Sure, you can go skiing at a major ski resort in the area. But for a little more wilderness and natural beauty, don’t miss local favorite Notchview, a 3,000-acre reservation that is gorgeous any time of year but a particular favorite in the winter. There are specific trails for classic cross-country skiing, skate skiing, and even “skiijoring,” or skiing with dogs (yes, that’s a thing!). Those who want to snowshoe or just explore can also go off trail into the wooded backcountry. If you don’t have your own gear you can rent skis and snowshoes at the Budd Visitor Center, as well as warm up with some hot chocolate and soup. —Route 9, Windsor | (413) 684-0148 | website6. Nudel


Photo by Ulf Nilsson

Chef Bjorn Somlo has been nominated for James Beard Awards multiple times so he’s not exactly under the radar, but many are still surprised to find a restaurant of this caliber in the Berkshires. The small, modern restaurant is situated directly in downtown Lenox, amidst a host of other good eats. But Nudel stands out for its imaginative take on seasonal American cuisine. The menu changes daily, but recent offerings have included things like fried chicken skin tacos, chevre and squash pate, veal and porcini mushrooms, and a “candy bar” of peanut butter, brownie, and marshmallow. They have recently started accepting reservations, but the walk-in only chef’s counter is the best seat in the house. —37 Church St., Lenox | (413) 551-7183 | website7. Shaker Dam Coffeehouse & Stanmeyer Gallery


Photo courtesy John Stanmeyer

When National Geographic photographer John Stanmeyer opened the Shaker Dam Coffeehouse & Stanmeyer Gallery in a nineteenth-century house in West Stockbridge in 2013, it instantly became a local favorite. The social justice–driven cafe serves ethically sourced, expertly prepared Counter Culture coffee and tasty goodies, while the upstairs is a gallery that displays Stanmeyer’s stunning photography. Shaker Dam also hosts frequent readings and other events to bring the community together, and the wood-burning stove makes it particularly cozy in winter. Stanmeyer himself can be found hanging out when he’s not off covering the migrant crisis in Europe or holy week in Jerusalem. —2 Main St., West Stockbridge | (413) 232-7707 | website8. Wandering Star Brewery


Photo courtesy Wandering Star Brewery

Wandering Star Brewery is pretty much the definition of “off the beaten path.” Located in a garage in Pittsfield, this 10-beer craft brewery was started by three friends who met through the New York City craft brew scene. They opened up shop in 2011 and have since developed a broad distribution base at bars throughout Massachusetts and New York, but there’s nothing like getting beer fresh from the source. Stop by most Saturdays from 12 p.m. to 3 p.m. to sample their brews, take a tour, and fill up a growler. Do call first to be sure, and note that this is not a brew pub. They change many of their beers seasonally, but year-round favorites include Second Breakfast (a session IPA) and Catnip (a white IPA). —11 Gifford St., Pittsfield | (917) 573-3942 | website>>Next: The Restaurant That’s Helping Transform Massachusetts’ South Coast

From Our Partners
Sign up for our newsletter
Join more than a million of the world’s best travelers. Subscribe to the Daily Wander newsletter.
More From AFAR