Berkshires Travel Guide: Where to Stay and What to Do in Berkshire, Massachusetts

For nearly two centuries, the Berkshires have been a popular destination for northerners looking to get away from it all. About two hours from Boston and three from New York, the area is an easy weekend getaway with a little something for everyone, whether you prefer world-class shows, outdoor adventures, a rejuvenating retreat or a slice of history. Sure, New England is known for its fall foliage (and fall is a popular time), but the region’s rolling hills, gorgeous light, quaint towns, and vibrant arts community make it a place to be. holidays of choice 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 lodges abound, but if you’re looking for a livebook a room at Miraval Berkshires-an indulgence you won’t regret. Opened in July 2020, the newest addition to the Miraval brand (you’re likely familiar with their original Arizona location) sits on nearly 400 beautiful acres, perfect for nature walks, equine therapy, golf, or just to relax. enjoy the beautiful scenery. It’s a feel-good 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: make sure you are present; cell phones and laptops are only permitted in certain locations. At first, this may seem boring (you’re going to want to post all about your trip), but soon you’ll find that it makes vacations much more enjoyable, relaxing, and educational if you live in the moment.

The 100 rooms are appointed with modern yet soothing interiors, including a Tibetan singing bowl and meditation cushion, but the piece de resistance is the bed, truly like snuggling up on a cloud. The cost of your room includes…virtually everything! All food and beverages (less alcohol) and all activities (unless a supplement is indicated) are covered. Before your stay, a concierge can help you plan all your activities (more on our recommendations, below).


Miraval Berkshires resort at sunset in winter

Part of Miraval Berkshires is Wyndhurst Manor (right), a former ‘Berkshire cottage’.

(Image credit: Chodos Photos)

what to eat

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

City dwellers who crave their morning all with lox and schmear can find their fix at Bagel and Brew in Lenox. Come back in the afternoon when the breakfast shop turns into a brewery, offering craft beers and loaded hot dogs. For a more elegant brunch or lunch, head to Zinc Bistro. Sip a French 75 while letting yourself be tempted by the crispy goat cheese salad and the grilled cheese with duck confit. (Too much cheese? Substitute the fried oyster caesar salad or the fried mussels.) If you’re traveling north to the Mass MoCA, arrive early and have lunch at the A-OK Berkshire BBQ onsite. The most popular spot is known for its homemade sausages and bread, but be warned: they stop serving when they sell out.

Ice cream lovers should save time for a trip to The Creamery of the Farm at High Lawn Farm. Relax at their picnic tables with a scoop of oreo coffee or pineapple cake or, if you fancy something savory, a cheese and charcuterie platter. For dinner, book at High, a cozy wine bar known for its sumptuous cuisine and excellent service. Food pairing recommendations are listed with each entrée, such as a Côtes du Rhône to accompany pan-fried duck breast and pan-fried cod in Sauvignon-Viognier.

What to do

What to do? It really depends on your interests. Here are some of the best options, although this list is by no means exhaustive.

Treat yourself to a day at the spa

If you need a little rest, put on a fluffy bathrobe and take a walk from your room to the Miraval spa. The 29,000 square foot facility features 28 treatment rooms where you can partake in Ayurvedic treatments, Reiki, vibrational sound therapy, or dozens of different scrubs, facials, or massages. Be sure to set aside time for lounging in the spa’s indoor/outdoor pool, perfect for relaxing by the water in any season.

A woman stands in front of the indoor/outdoor pool at Miraval Berkshires Spa

The indoor/outdoor lounge pool makes it easy to relax 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 sweating to spirituality: fitness classes include kickboxing, aquabar, and cardio drums to name a few; there are standard meditation classes but also a maze wisdom walk and sound immersion while wrapped in a yoga swing; aura photography allows you to visualize your energy; adventurous types may prefer to try a new hobby like archery – the more attentive you are, the more likely you are to hit the mark.

Admire the “Berkshire Cottages”

The Berkshires are not a new trendy destination. During the Gilded Age, many of the wealthiest Americans built summer homes in the area, which they affectionately called “cottages,” but they are the complete opposite of small. According to the book Berkshire Cottages: A Dying Era by Carole Owens, a “Berkshire cottage” was a second home with “no less than 20 bedrooms on no less than 30 acres”. No less than 93 houses of this type were built, mainly in the villages of Stockbridge and Lenox. Some were destroyed, but many still exist, many of which are now preserved in museums. Book lovers may want to visit Edith Wharton’s home, “The Mount”, or Herman Melville’s home, “Arrowhead”.

The Mount, the former home of Edith Wharton

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

(Image credit: Shutterstock)

Be artistic

Whether you like painting, sculpting, music or dancing, the Berkshires have what you are looking for. Contemporary art lovers should start Mass MoCA. Exhibits in this industrial space are usually large-scale and immersive, and visitors can often see the artists in the making. In Stockbridge you will find the Norman Rockwell Museumbringing together nearly 1,000 original pieces from the famous American painter and illustrator who lived in the region for a quarter of a century and often depicted the city and its people in his work.

Are you visiting the region in the summer? You’re lucky. Attend a concert by the Boston Symphony Orchestra at Tanglewood– formerly a Berkshire Cottage – the organization’s seasonal home. (The venue puts on shows year-round.) Meanwhile, dance-goers can picnic on the lawn at Jacob’s Pillow– a National Historic Landmark that is home to the famous dance festival of the same name – while watching performances by Ballet Afrik and the Boston Dance Theater, among many others.

Be outdoors

There’s no shortage of breathtaking vistas in the Berkshires, or trails to get you there, at varying levels of difficulty and lengths. You can even walk part of the Appalachian Trail at Mount Wilcox in the Beartown State Forest. In winter, the region offers plenty of terrain for snowshoeing or cross-country skiing. As we said, the area is a great place to visit any time of the year.