Just over the eastern Columbia border, Berkshire County is Massachusetts’ version of the Hudson Valley, with hip bustling towns, cultural hotspots, good eats, history, and boutique retreats—all surrounded by picturesque and hike-able mountains. It’s a perfect weekend destination—about 30–130 miles away depending on where you live in the Valley. Here is our short list of what to see and do in The Berkshires.
North
Eat & Drink
Gramercy Bistro, Williamstown: New American restaurant (try the paella) known for its selection of local beer and international wines.
PUBLIC Eat + Drink, North Adams: Share three types of flatbreads (Margherita, mushroom, peach and ham) or cheese boards, or just come for the crème brûlée.
The Distillery at Greylock WORKS, North Adams: Artisanal gins and rums at a former cotton-spinning mill that’s now a collaborative industrial space for events, markets, and more.

Get Outdoors
Mount Greylock State Reservation, Lanesborough: You can’t miss this mountain—it’s the highest peak in Massachusetts. There are over a dozen hiking trails, like popular treks: Rounds Rock and March Cataract Falls.
The Cascades Trail, North Adams: A relatively easy out-and-back trail with views of the 45-foot-tall “horsetail” waterfall.
Culture
The Clark Art Institute, Williamstown: A proper art museum with impressive galleries and stunning grounds. Abelardo Morell’s photographs following the footsteps of Claude Monet and John Constable will be on view beginning November 23.
Massachusetts Museum of Contemporary Art (Mass MoCA), North Adams: One of the region’s premier art museums, featuring intricate and immersive installations, large-scale wall drawings, and performance art.

Williams College Museum of Art (WCMA), North Adams: Check out the museum housed within Williams College, a top-rated private liberal arts institution, to round out your northern Berkshires arts trail.
Stay
The Williams Inn, Williamstown: Sixty-four guest rooms with farmhouse charm in the heart of downtown.
Tourists, North Adams: A stylish, acclaimed motor lodge that’s co-owned by John Stirratt, the bassist for the band Wilco. (He created Tourists Radio, which can be played in each room.)
Mid-County
Eat & Drink
Bistro Zinc, Lenox: Modern French eats (French onion soup, moules frites, fried oysters) with a swanky zinc bar.
Hilltop Orchards, Richmond: Year-round craft hard apple ciders (and donuts) and wine tastings at a 100-year-old red barn in the foothills.
The Lost Lamb, Stockbridge: This patisserie might ring a bell if you’ve been to Bimi’s Canteen in Chatham, which serves The Lost Lamb’s palm-sized macarons. Le Cordon Bleu alum Claire Raposo whips up classic French pastries and cakes, plus excellent baguette sandwiches.
Get Outdoors
Ramblewild, Lanesborough: Calling all thrill seekers! Unleash your inner child (and your kids) at this high ropes course deep in an alpine forest.
Laura’s Tower, Stockbridge: Trek over wooden bridges and moss-covered terrain to a lookout tower with grand views.
Culture
Berkshire Museum, Pittsfield: Remember those Hudson River School painters? Work from acclaimed members—like Thomas Hill and Albert Bierdstadt—are on view, along with other exhibits dedicated to natural history and ancient civilization.
The Mount, Lenox: Tour the historic Georgian Revival estate and outdoor sculpture gardens of Edith Wharton, the first woman to win the Pulitzer Prize for Fiction.

Tanglewood, Lenox: Catch a concert at this famous performing arts venue. It’s home to the Boston Symphony Orchestra and the Festival of Contemporary Music.
Norman Rockwell Museum, Stockbridge: Explore the largest collection of Norman Rockwell art in the world. (The late illustrator lived in Stockbridge for 25 years.)
Stay
Miraval Berkshires, Lenox: A luxury wellness resort with plenty of guest-only spa treatments (the Deep Mountain Massage is life-changing), fitness classes, and farm-to-table meals.
Blantyre, Lenox: A circa-1901 Gilded Age mansion-turned-destination that was modeled after a Scottish castle. It reopened in late fall.
South
Eat & Drink
MoonCloud, Great Barrington: Come for the eclectic cocktails (there are almost 20 to choose from) and stay for the tinned fish menu. Sit in the intimate lounge or front patio if weather allows.
The Prairie Whale, Great Barrington: Locals and tourists alike sing praises for this homey diner that serves seasonal comfort dishes.
Marjoram + Roux, Great Barrington: No-frills breakfast and lunch spot with delicious frittatas and pressed paninis.
Get Outdoors
Monument Mountain, Great Barrington: Spend a day hiking to the summit of this 1,642-foot peak. Fun fact: Authors Nathaniel Hawthorne and Herman Melville met on the trails of Monument Mountain and became fast friends while taking shelter from a rainstorm; Melville’s Moby Dick is inspired by and dedicated to Hawthorne.
Bash Bish Falls, Mt. Washington: These falls are super close to the Hudson Valley (less than 10 minutes from Copake) so a pit stop is a given. It’s a short-and-sweet hike with a big payoff: A series of cascades plummet over 200 feet for a stunning view during any season.
Culture
W.E.B. Du Bois National Historic Site, Great Barrington: Visit 17 sites around town—including Congregational Church, Searles Castle, and the town hall—that were influential in the life of this civil rights leader. Tour brochure available online.

Stay
The Barrington B&B, Great Barrington: A quaint and cozy bed and breakfast right on the main drag.
The Egremont Village Inn, South Egremont: This charming farmhouse has a wraparound porch, music venue, bar, and coffeeshop on the property. (Plus a few friendly goats and chickens.)
Related: 9 Boutique Outfitters for Outdoor Gear in the Hudson Valley