The Berkshires: Your Weekend Travel Guide

Where to stay, eat, and play in the western Massachusetts mountains.

Landscape in the Berkshires at Sunset
(Image credit: Shutterstock)

For nearly two centuries, the Berkshires has been a prized destination for Northerners looking to get away from it all. Just about two hours from Boston and three from New York City, the area is an easy weekend getaway with a little something for everyone, whether you prefer world-renowned performances, outdoor adventures, a rejuvenating retreat, or a slice of history. Sure, New England is known for its fall foliage (and autumn is a popular time), but the region’s rolling hills, gorgeous light, quaint towns, and vibrant arts community make it a choice vacation spot in all seasons. Here, where to stay and dine and what to do if you find yourself for a few days in the Berkshires.

Where to Stay

Inns and B&Bs abound, but if you’re looking for an experience, book a room at Miraval Berkshires—an indulgence you won’t regret. Opened in July 2020, the latest addition to the Miraval brand (you’re probably familiar with their original location in Arizona) sits on nearly 400 gorgeous acres, perfect for nature walks, equine therapy, golf, or just enjoying the gorgeous scenery. It’s a wellness resort, yes, but without the austerity of so many other properties in the category. Miraval is more about mindfulness and balance than weight loss and sacrifice. There are no calorie limits or mandatory fitness classes, and alcohol is served. Where they are restrictive: making sure you’re being present; cell phones and laptops are only allowed in certain locations. At first this might seem irksome (you’re going to want to post all about your trip), but soon you’ll find it makes for a much nicer vacation—one that’s more relaxing and enlightening—if you’re living in the moment. 

The 121 guest rooms are appointed with modern yet soothing interiors, including a Tibetan singing bowl and meditation cushion, but the pièce de résistance is the bed—truly like curling up on a cloud. Included in the cost of your room is…practically everything! All food and drink (minus alcohol) and all activities (except where a surcharge is listed) are covered. In advance of your stay, a concierge can help you plan all your activities (more on our recommendations, below).

BOOK IT

Miraval Berkshires resort at sunset in winter

Part of Miraval Berkshires is the Wyndhurst mansion (right), a former "Berkshire cottage."

(Image credit: Chodos Photos)

What to Eat

As mentioned, all meals are included in your stay at Miraval, and the farm-to-table fare (many ingredients are grown right on-property) is both healthy and tasty. But, you’re going to want to visit the charming surrounding towns, so you might as well take advantage of the great dining options there, too. 

City folk longing for their morning everything with lox and schmear can get their fix at Bagel and Brew in Lenox. Pop back in the afternoon when the breakfast shop turns into a brewery, offering craft beers and loaded hotdogs. For a more elegant brunch or lunch, head to Bistro Zinc. Sip on a French 75 while indulging in the crispy goat cheese salad and duck confit grilled cheese. (Too much cheese? Swap in the fried oyster cesar salad or moules frites instead.) If you’re traveling north to Mass MoCA, get there early and eat lunch at the on-site A-OK Berkshire Barbeque. The top-reviewed spot is known for its sausages and homemade bread, but be forewarned: They stop serving when they sell out. 

Ice cream lovers should save time for a trip to The Farmstead Creamery at High Lawn Farm. Relax at their picnic tables with a scoop of coffee oreo or pineapple inside-out cake, or, if you’re in the mood for something savory, a cheese and charcuterie board. For dinner, make a reservation at Alta, a cozy wine bar known for their sumptuous food and excellent service. Wine pairing recommendations are listed with every entree, like a Cotes du Rhone to go with the seared duck breast and pan seared cod with sauvignon-viognier.

What to Do

What to do? It really depends on what your interests are. Here are a few of the top options, though this list is by no means exhaustive.

Indulge in a Spa Day

If you’re in need of a little R&R, put on a plush robe and stroll from your room down to Miraval’s spa. The 29,000-square-foot facility features 28 treatment rooms where you can take part in ayurvedic treatments, reiki, vibrational sound therapy, or dozens of different scrubs, facials, or massages. Be sure to set aside time for lounging at the spa’s indoor/outdoor pool, perfect for waterside relaxation in any season.

A woman stands in front of the indoor/outdoor lounge pool at Miraval Berkshires' spa

The indoor/outdoor lounge pool makes relaxation easy in any season.

(Image credit: Indirap)

You could fill your entire weekend without ever having to leave the property. Other activities on offer range from the sweat-inducing to the spiritual: fitness classes include kickboxing, aqua barre, and cardio drumming to name a few; there are standard meditation classes but also a labyrinth wisdom walk and sound immersion while enveloped in a yoga swing; aura photography allows you to visualize your energy; adventurous types may prefer trying a new hobby like archery—the more mindful you are, the more likely to hit a bullseye.

Admire the “Berkshire Cottages”

The Berkshires are not a trendy new destination. During the Gilded Age, many of the wealthiest Americans built summer homes in the area, which they lovingly called “cottages”—but they’re quite the opposite of small. According to the book The Berkshire Cottages: A Vanishing Era by Carole Owens, a “Berkshire cottage” was a second home with “no fewer than 20 rooms on no less than 30 acres.” As many as 93 such homes were built, mostly in the villages of Stockbridge and Lenox. Some have been destroyed, but plenty still exist, several preserved as museums today. Book lovers may want to visit Edith Wharton’s house, “The Mount,” or Herman Melville’s home, “Arrowhead.”

The Mount, Edith Wharton's former home

The Mount, which Edith Wharton called home in the early 1900s.

(Image credit: Shutterstock)

Get Artsy 

Whether you’re into painting, sculpture, music, or dance, the Berkshires has what you’re looking for. Contemporary art fans should start at Mass MoCA. The exhibitions in this industrial space are typically large-scale and immersive and visitors can often witness the artists in the midst of creation. In Stockbridge, you’ll find the Norman Rockwell Museum, featuring nearly 1,000 original pieces by the celebrated American painter and illustrator who lived in the area for a quarter-century and who often portrayed the town and its inhabitants in his work.

Visiting the region in the summer? You’re in luck. Catch the Boston Symphony Orchestra in concert at Tanglewood—formerly a Berkshire Cottage—the organization’s seasonal home. (The venue boasts performances all-year.) Meanwhile, dance fans can picnic on the lawn at Jacob’s Pillow—a national historic landmark that’s home to the renowned dance festival of the same name—while watching performances by Les Ballet Afrik and Boston Dance Theater, among many, many others.

Be Outdoorsy

There’s no shortage of breathtaking vistas in the Berkshires—or trails to get you to them, at various difficulty levels and lengths. You can even hike part of the Appalachian trail at Mount Wilcox in Beartown State Forest. In the winter, the area offers plenty of terrain for snowshoeing or cross country skiing. Like we said, the region is an excellent place to visit at any time of year. 

Editor's note: This post has been updated to reflect the total number of guest rooms at Miraval Berkshires.

Danielle McNally is the executive editor of Marie Claire, overseeing features across every topic of importance to the MC reader: beauty, fashion, politics, culture, career, women's health, and more.