Where To Ski In The Berkshires? [Updated!]

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While there are plenty of great ski towns in New England, the Berkshires really do shine when it comes to offering skiing and apres-ski activities. From quaint villages to picture-postcard countryside, here are some great places to enjoy a fun-filled holiday in the great British country side.

North Creek

One of the most popular ski resorts in New England, and certainly the most convenient for those traveling from outside of the area, is North Creek in the towns of Williamstown and Warren. There are fantastic trails ranging from easy to expert, as well as nightlife in the town of North Creek itself.

Bordering the Massachusetts and New York state lines, this resort caters to skiers from all over the northeast, as well as some from further afield. The elevation is a little higher than that of the surrounding towns, so it offers fantastic views of the surrounding area, with the taller hills including Mount Equinox and Mount Pisgah providing a truly picturesque backdrop.

Great Barrington

Located in the center of the Berkshires, Great Barrington is a pretty town set within the scenic Connecticut River Valley. Home to Colby College and fed by the surrounding towns and forests, it draws an international student population thanks to its highly regarded schools, as well as a large number of affluent Bostonians looking for a taste of the countryside. Though there is no ski village per se, there is a lodge, several hotels, and various shops and galleries for those looking to make the most of the snowy season.

One of the most exciting aspects of a trip to Great Barrington is the opportunity to see the famous Mount Tom in all its glory. A real magnet for skiers, with trails such as the East Ridge and Panoramic Ridge, this iconic mountain dominates the horizon and provides breathtaking views of the Connecticut River and its surrounding towns.


On the southern tip of the Berkshires, lies the bustling town of Charlton. Boasting one of the best municipal parks in New England, as well as some decent Victorian architecture, this is a great place to stroll around the park and get some fresh air. There are several lodging options in town, plus a number of restaurants and bars.

If you’re looking to ski, you’re better off heading into the neighboring towns of Lenox or Great Barrington. The closest ski village to Charlton is situated in Great Barrington, though there are also a couple of smaller resorts nearby, such as Otter Creek and Fowler’s Ridge, which are just as popular as some of the bigger ones in more remote locations.


Nestled in the northern part of the state, near the Vermont border, Shawnee is one of the newest towns to be incorporated in Massachusetts. Having only officially opened its slope in 2015, the village offers some great challenges for beginner and intermediate skiers, with chairlift access to a backcountry that features breathtaking views of the lake. It also hosts a variety of outdoor activities, including picnicking, hiking, and fishing.

Though there are only a few ski trails in Shawnee, coupled with its young population, it’s set to become a major player in the New England ski scene. Its impressive five-star dining options and luxurious lodges should help it to establish itself as a hotspot for any holiday traveler.

Mount Cranmore

Often voted one of the top ten ski towns in New England, Mount Cranmore is one of the largest resorts in the area. Sitting right in the center of the scenic Berkshires, this snowboarder’s paradise draws strong community ties, with over 150,000 annual visitors flocking here from near and far to shred the fresh powder. There are twelve trails, ten of which are certified alpine, with spectacular views of the surrounding hills and valleys.

With a total elevation gain of 989 feet, this is one of the most popular destinations for skiers and snowboarders, with the ski season extending from as early as October to as late as April. In addition to the slopes, there is also a very popular snow park, featuring mega-trick jumps, rails, boxes, and other complex features for snowboarders of all abilities.

Since the 1960s, this picturesque mountain has attracted skiers from all over the world, with many referring to it as the ‘Valhalla of the West’ due to its iconic status. It’s no surprise that with its fabulous location right in the heart of the American countryside and its impressive snowfall, this is one place that you don’t want to miss out on when the holiday season rolls around.


As the oldest town in the Berkshires, Montabella draws a range of tourists, from families with young children to groups of 20-somethings. Sitting at the confluence of the Otter Creek and Connecticut Rivers, this village draws visitors from far outside the immediate area, with many people making the trip specifically to ski here. There is a large hotel as well as some smaller resorts nearby, including the even more historic Alton Mountain, which is just a stone’s throw away.

Known for its extreme slopes and nightlife, as well as its spectacular views of Mount Tom, this is one of the premier ski towns in New England. There are thirteen trails here, which are all pretty accessible, and the steepest one, the Bald Peak Trail, offers some of the best views of Mount Tom.

With a total elevation gain of 2,322 feet, this Massachusetts resort is a bucket-list destination for skiers and snowboarders. Its trails meander through the woods alongside the scenic rivers, while the snow park features a supertrail, supertrail combo, and a snowboard park for beginners and pros alike.

Whistle Stop

Located in the northeastern part of the state near the Canadian border, Whistle Stop is home to an eclectic mix of artists and craftspeople. Though there are only a few trails here, due to its remote location, those in the know make the trip to explore the backcountry. The only lodging option is a tiny former post office, but it doesn’t matter because there are plenty of nearby towns where you can stay. This is a great place to get away from it all and reconnect with nature.

Nestled in the Green Mountains, you’ll find this beautiful town, complete with cobbled streets, brick houses, and colorful foliage. It’s well-known for its festivals, particularly its Strawberry Festival, which is held in the last week of April and includes live music and dancing. The town is also home to the New England Aquarium, offering a glimpse of what aquatic life is like in the wild and the chance to see some spectacular creatures up close and personal. With Lake Monterey as its backyard and the front door to the Atlantic Ocean, this quintessential New England town is a definite hotspot for any visit in the winter.


Walden is located in the North of the state, though it’s pretty accessible from anywhere, especially with there being two decent-sized ski resorts, Mount Wachusett and Mount Washington, both of which are easily reachable from Boston. Walden village itself is a mecca for antique collectors, with a good number of galleries and shops to browse through. There is also a very well-stocked bookstore and nice pubs and restaurants dotted around the tiny village, which is perfect for those looking for some socializing.

As the name would suggest, Walden is a real-life scene from the literary masterpiece, The Mill on the Floss, by George Eliot. The author of Middlemarch, also set in the English countryside, and Daniel Deronda, set in the early 20th century, both published in the 1860s, Eliot spent many of her later years in Walden and is buried in the churchyard. Today, the author’s house, Kelmscott, is open to the public as a museum and serves as a quiet reminder of one of literature’s most brilliant and intriguing female authors.


Northeast of Boston, yet somehow still within Massachusetts, lies Northampton. Visiting either the downtown area or the Smith College, where Emily Dickinson wrote much of her work, is a good way to get an insight into the life of America’s greatest poetess. Besides the literary sights, Northampton is also a hub for the performing arts. If you visit in the winter, you’ll find the Smith College Theatre, where the famous American Musical Theatre Company performs, as well as the Colonial Theatre, which presents plays and musicals. Additionally, the Northampton Museum of Art, the Phillips Collection, and the Davis Museum of Art are just a few of the local museums that you can visit.

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