In Massachusetts, Boston seems to get all the attention, yet there are many ski towns in the western and northern parts of the state that deserve their own recognition. These alpine communities are filled with activities, culture, and entertainment at all times of the year, perfect for a short visit or a lifetime.
The four ski towns are a short distance from either Springfield or Worchester, the state’s other two largest cities. Culinary and shopping choices abound in these communities as well as quick access to the slopes. Consider making the Massachusetts mountains your next vacation spot or hometown.
Here are the top ski towns in Massachusetts to live and visit, in no particular order:
Charlemont, MA
Among the farms and hills of northwestern Massachusetts is Charlemont, a ski town in the Berkshires that was settled in 1744. The rural community isn’t far from Springfield and had a population of 1,185 people in the 2020 census.
The family-owned Berkshire East Mountain Resort is just minutes away from Charlemont. The ski area has a classic New England ski resort vibe and was once among five ski areas located in the vicinity.
Today it’s the only one remaining, surviving bankruptcy and oddly the theft of its original rope tow. In the winter, snow tubing and ski racing are available on the mountain, or find ice skating and cross country skiing in the surrounding area.
In the summer, Berkshire East adds an adventure park and an incredible mountain coaster to its list of outdoor activities. That list also includes whitewater rafting, mountain biking, ziplining, and open-mic nights at a local eatery.
Charlemont was incorporated in 1765, likely the namesake of an Irish town. Farming is still one of the area’s primary industries, and today the town is home to both professionals and retirees. The community is filled with cafes, general shops, and several restaurants along its scenic primary route.
Lenox and Pittsfield, MA
One is a ski town, the other a ski city. These two communities to the south and north of Bousquet Mountain Ski Area offer everything a skier and snowboarder could need all within a quick drive of the slopes.
Despite its size, the city of Pittsfield is still a ski town at heart. It may have its own airport and a population of nearly 44,000 in the 2020 census, but the ski slopes and rolling hills within view of city streets make it feel like a cozier place to live or visit. The city was incorporated in 1761 and was an agricultural center, in particular for sheep farming and woolen manufacturing.
The posh town of Lenox, with a population of around 5,000 in 2020, was originally a town full of farmers, innkeepers, and merchants. When a vein of iron ore was discovered beneath the town, mining became part of the community.
The region was a haven for artists and writers, including Nathaniel Hawthorne, Catharine Sedgwick, Edith Wharton, and Herman Melville. It’s also home to Tanglewood, the Boston Symphony Orchestra’s summer academy.
Art shows, museums, live music, and theaters can be found in any season, but during the winter months, many people visit the Pittsfield State Forest for backcountry skiing, snowmobiling, and snowshoeing. With so many opportunities in both Lenox and Pittsfield, the area is a perfect place to live or stay.
Great Barrington, MA
The funky little ski town of Great Barrington is filled with cool shops and walkable streets, yet is surrounded by mountains and trees. It’s a community known for having an urban vibe while maintaining a low population of just over 7,000 in 2020.
Butternut Ski Area is a few miles down the road, offering ski racing, tubing, and terrain parks along with downhill skiing and snowboarding. In the summertime, take a walk along the Housatonic River, which connects many of the communities in the Berkshires. Or explore a family farm, swim in Lake Mansfield, or hike Monument Mountain.
The tree-lined Main Street with historic brick and stone buildings leads through town, winding past old homes and dozens of shops and restaurants. There are many hotels and inns in the area, with farmsteads, galleries, and a summer concert series.
The recorded history of this southern Berkshires ski town dates back to the 17th century. It eventually became a resort community and today it’s a popular place for second homes as well as full-time residents.
Westminster and Princeton, MA
At the base of one of Massachusetts’ highest points is Westminster, a small New England ski town surrounded by a rural community. Located just minutes to the north of the resort, the town encompasses both the mountain and Wachusett Mountain Ski Area, making the area a great one to visit or live in.
About equal distance to the south, a mere 7-minute drive is Princeton, MA, which sometimes shows up on the Wachusett Mountain Ski Area address. In 2020 it had a population of 3,495. This rural community of rolling forested hills is a lovely destination year-round.
In the winter it’s common to find people snowshoeing around the ski area or cross country skiing the trails of Leominster State Forest. Summertime means canoeing, kayaking, hiking, or fishing throughout the area.
Both towns were incorporated in 1759 and have had a fairly sleepy existence since then. Crackers are a big part of the area’s history and are celebrated with an annual Cracker Festival or a tour of the original Westminster Cracker Company factory.
Westminster had a population of more than 8,000 residents in 2020. There are a handful of hotels and shops around Westminster, but plenty of dining options including the old mill and local brewery.
Massachusetts has over a dozen ski areas, many of which are located in the Berkshires in the western part of the state. These resorts offer a wide diversity of terrain for downhill skiing and snowboarding, and many slopes offer adaptive skiing.
Anyone discovering these ski towns will find quaint, unique streets and plenty to do and see at any time of the year. With plenty of cultural and outdoor activities, the top mountain towns in Massachusetts are great places to live or visit.
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