The Best Things to Do in the Berkshires—and Where to Stay

Like much of Massachusetts, the Berkshires are deeply rooted in history. Great American names in art and culture—Melville, Hawthorne, Wharton, Rockwell—have called it home, and the creative spirit is truly alive and well here. I first visited the Berkshires in college to perform at what I can only call a very Western Massachusetts modern dance festival and have had the privilege of visiting the home of dear friends from Boston across many years and seasons since. Unlike the nearby Hudson Valley (too cool?) or Litchfield County, Connecticut (too tradwife?), where so many New Yorkers decamp from the city, a few days among the rolling hills of the Berkshires has always left me feeling completely reset.

Technically, Berkshire County is the westernmost slice of the state, though in practice you’ll probably find that application is slightly more generous. There are several larger towns to anchor your visit around: Great Barrington, Lenox, and Stockbridge in the west, North Adams in the northeast. Drive about an hour to Hudson, New York, in one direction or around two hours to Boston in the other. In between, you’ll find hiking and skiing, venerable cultural institutions, farm-to-table food and historic landmarks to keep you entertained, all set against a lush, pastoral backdrop.

One of the latest additions to the region, Prospect Berkshires, opened in 2025 in the delightfully sleepy Egremont, and is designed to embrace nature as its number one amenity. Forty-nine individual, Scandi-inspired cabins are situated along Prospect Lake, where swimming, kayaking and paddleboarding are provided for and encouraged. Made for the active traveler, saunas are peppered throughout the property—including two directly on the lake—as are a tennis court and a freshly finished pool.

Just down the road (and technically in New York state), Little Cat Lodge has a slightly more alpine-chic-meets-motor-lodge vibe. In nearby Richmond, Massachusetts, The Inn at Kenmore Hall is a boutique hotel in the form of a stately Georgian home, owned by the former head of menswear at J.Crew, designer Frank Muytjens and his partner, restaurateur Edward Scott Cole.

For something more traditional, the Red Lion Inn in Stockbridge is a well-known haunt to both tourists and locals that has been in operation since 1773. Though it was destroyed in a fire and then rebuilt at the turn of the 20th century, it has housed many storied guests since, including multiple US presidents, Judy Garland, and Bob Dylan. It also has the distinct honor of being the former workplace of Real Housewives of New York City alum and longtime Berkshires resident Dorinda Medley.

If you’re looking to be closer to the art action, Tourists Welcome in North Adams is just a six minute drive from MASS MoCA and three minutes to Williams College. Here, the iconic roadside motel is given a woodsy—also Scandi leaning—makeover, and the property recently expanded beyond its 46 rooms with the opening of two nearby private homes, one five-bedroom and one two-bedroom.

Lenox, with its many boutique hotels, is another great place to call home in the Berkshires. Each of the rooms at interior maven (and Berkshire native) Annie Selke’s inn 33 Main has its own artistic flair and personality, and touches like complimentary breakfast and cocktail hour in the parlor make staying here feel truly convivial. Locally based couple Kelly and Bryan Binder run the nine-bedroom Doctor Sax House, and while the refreshed wall dressings and plush bedding don’t show it, the property dates back to the Gilded Age.

What to do in the Berkshires

We’ll get to all the nature and history shortly, but first let’s talk about newness in one of my favorite arenas: shopping. This July, Walker Street Market, a new design gallery with works from more than 70 contemporary artists, opened right on one of the main drags in Lenox. I had the opportunity to attend the opening and was delighted to mull over delicious smelling candles, handmade Japanese ceramics, and mind bogglingly cool baskets from Underwater Weaving. Founded by former fashion designer Matthew Ames, the impeccably curated space features rotating collections from some of the most exciting makers around.

The Berkshire Galleries in Great Barrington is another great stop for antiquing, and the town's Main Street is well-suited for a leisurely afternoon of strolling and shopping. There are plenty of shops for vintage and new clothing; Fluff Alpaca stocks cozy sweaters and throws in addition to more tailored pieces like blazers and pants, and One Mercantile features an eclectic selection of linens, soaps, and locally made gifts; next door, the team operates SETT, a kitchen goods store with high-quality dining and serving wares. Take a break at Fuel, a popular spot for breakfast sandwiches and coffee, or enjoy a cone outside of SoCo Creamery, a local ice cream parlor with classic and less-common flavors (think Marzipan Date Orange Zest, and Lemon Basil).

A visit to the Berkshires would not be complete, in my opinion, without a visit to Tanglewood or Jacob’s Pillow for some live music or dance, respectively. MASS MoCA is also a must-see; the former industrial space, impressive in its own right, is now one of the largest museums in the United States and is venerated for its contemporary programming. Further south in Stockbridge, the Norman Rockwell Museum in the artist's hometown has a collection of almost 1,000 original drawings and paintings.

Fans of the Shakers won’t be disappointed. In Pittsfield, Hancock Shaker Village is a wholesome, family-friendly affair with farm animals included. In 2028, the region will also be home to the Shaker Museum, a second destination dedicated to the group’s pursuits in Chatham, New York. In the meantime, the Shaker Outpost is hosting seasonal exhibitions.

The natural beauty in this part of Massachusetts really can’t be understated. The landscape—with the Taconic Mountains, the Housatonic and Connecticut Rivers, and no shortage of woods—make for year-round splendor (the leaf peeping season is deeply underrated). The area also provides endless hiking and, in the winter, multiple skiing ranges for a little more active adventure. For one of the best views of the Housatonic River Valley (especially at sunrise), hike up Monument Mountain's three trails, each of which are under three miles long. Or to get a view of the Appalachian Trail, hike up Mount Greylock, which also happens to be home to the highest point in the state of Massachusetts. And in Stockbridge, the Charcoal Trail leads to Olivia’s Overlook for a stunning vantage point of Stockbridge Bowl lake and the surrounding area.

To enjoy art outdoors, guided tours are available on weekends from May through October at Chesterwood, a sculpture garden and studio that once belonged to Daniel Chester French, an artist who crafted, among many other pieces, the monumental Lincoln Memorial sculpture in Washington, DC. For the literary-inclined, author Edith Wharton’s Lenox home, The Mount, is open to visitors—the 45-minute garden tour is especially stunning in the spring.

Best restaurants in the Berkshires

Though the dining scene in the Berkshires is more quality than quantity, you’ll find options whether you’re looking for a casual roadside joint or a fine dining experience. If you’re starving for options, keep in mind that, depending where in the Berkshires you’re calling home, the many restaurants of Hudson and Stissing House in Pine Plains are also within an hour or so drive.

That the food is yummy and the vibes are immaculate at Prairie Whale is no mistake. One of its owners, Mark Firth, is a cofounder of Brooklyn Diner and the now sadly closed Marlow & Sons. The space feels like an old-school tavern that's always been there with its dark, ramshackle wood paneling and hodge podge vintage art collection, though in reality it opened in 2012. Expect excellent fries and a strong cocktail.

Come for the ice cream, stay for the baby cows—High Lawn Farm is a popular attraction for those with kids and no dairy intolerances. Bring some cheese and butter home for later. Speaking of cheese, Rubiner’s Cheesemongers in Great Barrington is the spot for grabbing your provisions. It’s also a favorite of local food icon Ruth Reichl. Its sister cafe, Rubi’s, offers no fewer than five different grilled cheeses and a solid roster of non grilled cheese sandwiches.

The restaurant at Prospect Berkshires, The Cliff House, is one of the more upscale options for dinner or a Sunday brunch. Arrive early to enjoy the lakeside view (which really is something to see), and dine on locally sourced ingredients prepared with minimal fuss. You’ll find hearty staples like a roast chicken, Faroe Island salmon, and pork as well as inventive cocktails.

No Comply, another newbie, is an alcohol-free restaurant with a skater spirit. Their creative egg dishes snagged them a spot on Bon Appetit’s “Best New Breakfast Spots” list in 2025 and the thoughtful dinner menu, served Wednesday through Saturday, makes even a veggie burger a special event.

There’s always a line for West Stockbridge’s No. Six Depot, a husband and wife-operated roastery that has been keeping the region caffeinated for over a decade; and a subscription to their coffee club is a souvenir that keeps on giving. Pair your morning latte with a croissant or three from the Lost Lamb, a Stockbridge patisserie run by a Le Cordon Bleu graduate.

The Berkshires might not be the first place that comes to mind for authentic Neapolitan-style pizza, but Pizzeria Boema has perfected the art of the super-crispy crust. Build your own pie or choose from one of the house classics, and don’t miss Monday Night Jazz events during the summer. For more comfort food, Great Barrington's Bistro Box, a seasonal pop-up with a cult following around its comfort food-centric menu, features BLTs, tacos, slushies, and more from April through November. In West Stockbridge, the Heirloom Lodge is a sleek fine-dining spot with farm-to-table fare and a focus on wines from family-run vineyards; chef and owner Matt Straus is the editor of literary food magazine Kitchen Work.

This article has been updated with new information since its original publish date.