I used to think of the Berkshire Mountains in Massachusetts as a summer destination, where I’ve watched the summer performances of the Boston Pops at Tanglewood, hiked Monument Mountain, and traversed the treetops at Ramblewild. But with snow-covered mountains, ice-coated lakes, and world-class cultural attractions, there is plenty to do in the Berkshires in the winter.
If you are looking for a winter weekend getaway from Boston or New York, but you don’t want to go all the way to Vermont or New Hampshire, it is time to discover the Berkshires in the winter. You can go skiing, snow tubing, snowshoeing, ice skating, ice fishing, cross-country skiing, or hiking. And if you would rather stay out of the cold, you can explore miles of art galleries, visit historical sites, or relax at award-winning spas.
In the Berkshires, you can also stay at cute boutique hotels, historic inns, or slope side condos and enjoy fine dining or cute cafes. Ready to go? Just follow these suggestions for a wonderful winter weekend getaway whether you are looking for a romantic getaway, visiting the Berkshires with kids, or just want a fun time with friends.
Things to do in the Berkshires in the Winter
Editor’s note: I revisited the Berkshires in the winter as part of a press trip hosted by Explore Western Mass. All opinions are my own.
Indoors or outside, you will find plenty to do in the Berkshires in the winter.
Go Snow Tubing
Snow tubing isn’t just for kids (trust me, this 53-year old still loves it). Bousquet Mountain is a local ski mountain near Pittsfield, Massachusetts that offers evening snow tubing on Thursdays through Saturdays and daytime sessions on weekends and holidays.
Bousquet is the fifth oldest ski mountain in the USA and the first to offer night skiing, but recent investment has yielded a new lodge with a cozy upstairs lounge and restaurant. The ski resort gets busy with local school groups and ski lessons, but you don’t have to wait long for one of the four snow tubing lanes and the magic carpet lift means you don’t need to lug your tube back uphill either.
You can also go snow tubing at Ski Butternut, which is closer to the Connecticut border, Catamount Mountain Resort on the New York border, or Berkshires East, in the northern part of the Greater Berkshires.
Learn to Ski or Snow board
There are five ski mountains in the Greater Berkshires that offer lessons for downhill skiing and/or snowboarding. Of the five, three of these mountains participate in the Indy Pass. The Indy Pass gives you two free lift tickets and a third discounted day at each one of the participating Partner Resorts (but reservations are needed.)
If you are looking for a family-friendly ski weekend, Jiminy Peak is the place to go. As the largest ski resort in Southern New England, Jiminy Peak is a true four-season resort with a small ski village at the base offering condos for rent and multiple lodges. They offer a full kid’s program with the KidsRule Mountain Camp, which includes full day instruction, lunch, and plenty of hot cocoa breaks. If your kids don’t want to ski, no worries, you can sign your child (two and older) up for the on-site childcare at Cub’s Den Playroom.
At Jiminy Peak, you will find 45 trails, serviced by nine lifts, along with snowshoeing trails, a mountain coaster, and an alpine slide and aerial adventure park in the summer. And the amazing part is that the resort operates entirely on renewable energy.
If you prefer a more local feel, and cheaper lift tickets, try the aforementioned Bousquet Mountain or the more rustic Berkshires East. Located in Charlemont, Berkshires East is the most northern of the ski mountains in this area. In the summer, families can enjoy the Mountain Coaster, zip lining, the Thunder Mountain bike park, or even nearby whitewater rafting.
But in the winter, this family-owned and operated ski mountain offers ski and snowboard lessons, ski racing, snow tubing, a new high-speed detatchable quad lift using 100 percent renewable energy. I enjoyed a bluebird day on the slopes and thought for sure I would encounter lots of ice from recent rainstorms but the snow making was top-notch and there was plenty of powder.
Try SnowShoeing
Ever since my feet started giving me issues when I was on a ski trip in Idaho, I’ve started to prefer snowshoeing over skiing. There is something very relaxing about the quiet of the woods and the rewarding exertion of tramping through the snow.
There are many places to enjoy snowshoeing in the Berkshires, such as Notchview, where you can snowshoe alongside of 25 miles of cross-country trails. Maple Corner Farm also has 10 kilometers of snowshoe trails, along with equipment rentals for children through adults.
But you don’t need to go out of your way to try snowshoeing! Jiminy Peak offers both equipment rentals and a network of backcountry trails so that you can snowshoe while others ski.
Ride a Mountain Coaster
Even if you don’t like roller coasters (that would be me), you will probably enjoy a ride on a mountain coaster. On a mountain coaster, you are seated in individual carts and you control the speed using a simple braking mechanism. Each car is pulled up the metal track and then released at the top. Then you travel down the twists and turns at your own pace.
Don’t worry, you are buckled in and the cart can’t fly off the track! I love it and I’m not a ride person, at all. Multiple resorts offer mountain coasters, including the one at Jiminy Peak.
Get Acquainted with Contemporary (and other) Art
The Berkshires are known for music and art, with a selection of art museums including The Clark, the Williams College Museum of Art, the Berkshire Art Museum, and the Norman Rockwell Museum.
The most famous is Massachusetts Museum of Contemporary Art. Located in a converted Arnold Print Works factory building complex in North Adams, Mass MoCA is one of the largest centers for contemporary visual art and performing arts in the United States, covering over six miles of galleries. It is no wonder that tickets are valid for two days to give you plenty of time to explore and absorb.
Unlike other contemporary art museums, the installations at Mass MoCA are not part of a permanent collection, but on loan from the artists or other collectors. Many of the exhibits are created specifically for this site and the majority are large form installations. You will want to take time to observe in the art, read about the artists and the learn the meaning behind the piece or installation, and just enjoy the experience.
Visit a Living History Museum
Hancock Shaker Village is a National Historic Landmark and a living history museum that showcases the history of the Shaker people, who settled in the area in the 1780s and lived there for 170 years. The Shakers lived communally, farming and creating high quality products such as furniture.
Today, you can visit the village and see the historic buildings, including the famous Round Barn, and visit various workshops with live interpreters. During the February “Big Chill” weekend, you can enjoy walking tours, watch ice sculpting, see maple tree tapping, and observe blacksmithing and woodworking demonstrations. Families will appreciate the face painting, farm animals, and snacks by the fire.
Relax at the Spa
The Berkshires is home to two luxury spas and one yoga retreat (which is unfortunately closed in the winter.) If you are willing to make a big splurge, book a stay at either the Miraval Berkshires or Canyon Ranch Berkshires. Even if you don’t stay over night, you can still book a day pass. The Miraval day spa package includes a resort credit to be used towards services along with a gourmet lunch, complimentary snacks and smoothies, participation in complimentary yoga, meditation, fitness classes, and wellness lectures, and full spa amenities.
Sample Maple Syrup
Mid-February to mid-April is sugaring season in the Berkshires and everywhere you drive, you will see the plastic tubing connecting the maple trees and transporting the sap for processing. Visit the Maple Corner Farm on the weekends for pancake breakfasts, maple sugaring demonstrations, and shopping for everything maple.
Where to Stay in the Berkshires
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Hotel on North
I’m a big fan of boutique hotels and if you are too, you will love Hotel on North in Pittsfield. Located in the heart of this small town, Hotel on North pays tribute to the area’s artistic roots, proudly displaying the work of local artists in the lobby and the spacious rooms.
In this 45 room boutique hotel, each room has its own individual design featuring locally-crafted furniture and luxurious finishings.
See more photos and read reviews
Williams Inn
The Williams Inn is a new upscale inn in the heart of Williamstown, within walking distance to Williams College, shops, and restaurants. This 64-room hotel uses upscale, contemporary farmhouse design with luxurious amenities and serene, spacious rooms.
The hotel uses energy-saving features to reduce energy consumption by more than 40 percent and I’m a huge fan of the coffee, tea, ice, and water refill (still or bubbly) stations. Plus it is lovely to not even need to leave the hotel for dinner after a long day on the slopes, just book a reservation at The Barn restaurant for fine dining featuring American classics.
See more photos and read reviews
Jiminy Peak Vacation Rentals
Jiminy Peak Mountain Resort offers many privately-owned condominiums that are ideal for families and groups. There are two to four-bedroom units that offer generous living rooms, full kitchens, and even washers and dryers. You can book online through a central booking system and others are available through Airbnb and vrbo.
Red Lion Inn
If you prefer a historic inn, try the Red Lion Inn in Stockbridge. You will be a little further from the slopes but you can enjoy the legacy of 250 years of hospitality. Accommodation options include rooms at the original Main Inn, a more contemporary guest house, and unique lodging options, including a turn-of-the-century Firehouse.
This hotel offers all the modern amenities you desire, including a heated pool, hot tub, fitness room, plenty of dining options, and even live entertainment. It is extra special at Christmastime.
Where to Eat in the Berkshires
Dottie’s Coffee Lounge, Pittsfield
Dottie’s Coffee Lounge in Pittsfield is the kind of place you just want to hang out after some outdoor winter fun or hours exploring museums. With multiple, interconnected rooms, it is easy to find a comfy corner to enjoy freshly-ground coffee, homemade pastries, and fresh, organic food. It is also a perfect spot to fuel up for a busy day and Dottie’s has some creative menu items like the “Healthy Elvis” breakfast sandwich or the “Grilled Ghee”, which is a step up from a simple grilled cheese.
Tunnel City Coffee, Williamstown
If you stay at the Williams Inn, it is just a short jaunt across the street to grab coffee and breakfast at Tunnel City Coffee. This specialty coffee roasting company has a small batch roasting operation and two cafes, one in Williamstown and the other at Mass MoCA. In addition to your hot beverage of choice, Tunnel City offers bagels, baked goods, and some simple breakfast sandwiches.
John Harvard’s Restaurant & Brewery, Jiminy Peak
If you are hitting the slopes at Jiminy Peak, you have multiple dining options from the simple food court to a grab and go coffee shop and sit down dining. For upscale dining, try John Harvard’s Restaurant, located on the third floor of the Country Inn. John Harvard’s offers classic American cuisine with hearty portions such as burgers, fish sandwiches (which are huge), clam chowder, French onion soup, and more.
Crazy Horse Bar & Grill, Berkshires East
For a somewhat rustic lodge setting at the Berkshires East, the Crazy Horse Bar & Grill is a comfortable spot to relax and enjoy food and drinks after a day or morning on the slopes. Located upstairs in the Main Lodge, there is even a terrace overlooking the trails that you can enjoy in sunny weather. Crazy Horse serves up your typical pub food such as wings, Bavarian pretzels, poutine, burgers, and more.
Methuselah Bar & Lounge, Pittsfield
The Methuselah Bar & Lounge in Pittsfield has a simple menu, but the food packs a huge punch. The food features organic, locally-grown options whenever possible and takes simple dishes (like pigs in a blanket) and brings them up a notch. I’d suggest gravitating toward the Korean-inspired options like the Korean bibimbap, which is topped by the juiciest and most tender Korean Kalbi meat. My mouth is watering just remembering that dish!
The Barn, Williamstown
The Barn Kitchen and Bar is located in the Williams Inn and while the outside may have some barn-like characteristics, inside it feels like a rustic fine dining establishment with soaring ceilings, an impressive bar, and high-touch service. The menu features New England classics and seasonally-inspired, locally-sourced cuisine that works for the whole family with dishes from macaroni and cheese to roasted duck.
You May Also be Interested in…
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- 40 Fantastic weekend getaways from Boston
- Skiing near Boston
- Day trips from Boston
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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.
