Find the Best Things

Explore Thrilling Winter Activities in Massachusetts

ma winter activities

Bay Staters know a thing or two about making the most of the winter. In New England, we are regularly blanketed by a snowy wonderland. With the clean, crisp air in your lungs and endless outdoor activities at your disposal, it’s time to bundle up and have a true Massachusetts winter experience. These are our favorites.


Hit the slopes at Wachusett Mountain, Princeton, MA

Skiing at Wachusett Mountain in Princeton isn’t just fun—it’s family-friendly, too. Package plans for four or more make skiing all winter affordable. The mountain even presents a comedy night at the lodge once per week.

Cross-country skiing at Weston Ski Track, Weston, MA

Cross-country skiing is a winter pastime often associated with wide open snow-covered fields. And while that’s the beauty of living in rural Massachusetts, what are those who live in the city to do if they want to partake of this winter activity, too? Weston Ski Track is the answer to their dilemma. Located just 15 minutes outside of Boston, the track not only affords a place to ski, they even offer cross-country ski lessons.

Snow-shoeing on the North Shore, Topsfield, MA

Massachusetts folks on the North Shore dig out their snow shoes each year when snow covers the ground at Bradley Palmer State Park Trail in Topsfield. The main road into the park is plowed throughout the winter, and snow shoeing on a three-mile loop trail is a wealth of winter fun—not to mention it’s excellent exercise.

Ski Butternut, Great Barrington, MA

Weekday lift tickets at Butternut Mountain in Great Barrington make it an excellent place for affordable downhill skiing. Twenty percent of the slopes are black diamond rated. This means that while it’s affordable, it isn’t merely a hill. Even the best skiers can enjoy their time on Butternut’s slopes.

Skate at Canal District Kendall, Cambridge, MA

Even though indoor ice skating arenas are plentiful in Massachusetts, there’s nothing quite like skating outdoors. Community Ice Skating @ Kendall Square in Cambridge is a wonderful place for skaters of all ages and abilities to give the ice a try. Featuring ice skating lessons for all ages and ice skate rentals, be sure to contact the rink for group rentals or private parties. Hot chocolate, coffee and snacks are available at an on-site snack bar.

Canterbury Farm, Becket, MA

Canterbury Farm is located high in the Berkshire hills in the town of Becket. Just under 20 miles of trail systems are groomed specifically for cross-country skiing. Rentals are available. It’s a beautiful spot to spend the day.

Clarks Pond, Amesbury, MA

For outdoor ice skating, north of Boston, visit Clark’s Pond. Located just off Cedar Street in Amesbury, the pond is perfect for families with kids, and has its own parking lot adjacent to its dam. Check with city hall if you’re questioning whether the ice is thick enough for safe skating. Parking is limited.

Berkshire East Mountain Resort, Charlemont, MA

The Berkshires are home to some of the best skiing in Massachusetts. Berkshire East Mountain Resort offers some of the most popular trails in the state. There are slopes for everyone in the family regardless of what level skier they are.

Hilltop Orchards, Richmond, MA

Hilltop Orchards in Berkshires is home to some exceptional cross-country skiing if there’s snow on the ground. Featuring both group and private lessons, as well as equipment rentals, their Barrel Room even offers a comfy place for non-skiers—or those looking to warm up—a place to enjoy some apple wine and the scenery.

Nashoba Valley Ski Area, Westford, MA

Nashoba Valley in Littleton is known for its skiing, but did you know they have slopes designated for snow tubing as well? Visit the website to learn when they open for the season. Open for tubing seven days a week, check for hours once the season opens. Snow tubers must be six years old or at least 42 inches tall to take part in this outdoor fun.

Walden Pond State Reservation, Concord, MA

If you’re from Massachusetts, you likely already know that Walden Pond is home to author Henry David Thoreau—but did you also know that Walden Pond State Reservation Trail is home to some excellent snow-shoeing during the winter months? The 1.7-mile trail is flat, which makes it perfect for beginners and children. Intermediate show-shoers can do the trail in about two hours.

Ski Ward Ski Area, Shrewsbury, MA

Eight lanes and two lifts make snow tubing at Ski Ward in Shrewsbury exemplary. Over 200 tubes are available to rent. Before tubing, all tubers must read the Ski Ward rules and sign a consent form.

Maple Corner Farm, Granville, MA

A working farm since all the way back in 1812, Maple Corner Farm in Granville is home to some fine snow-shoeing trails in the winter. Just over six miles of marked trails grace the farm, where outdoor enthusiasts can go cross-country skiing, too. A cozy wood fire and snack bar make warming up a breeze. Snowshoes are available for rent.

Key Insights at a Glance

  • Wachusett Mountain: Enjoy family-friendly skiing with package plans and weekly comedy nights at the lodge.
  • Weston Ski Track, Weston, MA: Located near Boston, this facility offers cross-country skiing and lessons, ideal for city dwellers.
  • Snow-shoeing on the North Shore: Explore Bradley Palmer State Park on snowshoes along a three-mile loop trail, accessible via a plowed main road.
  • Ski Butternut: Offers affordable weekday lift tickets and challenging slopes, including 20% rated as black diamond.
  • Canal District Kendall: Outdoor community ice skating with lessons available, skate rentals, and a snack bar serving hot drinks.
  • Canterbury Farm: Provides groomed trails for cross-country skiing in the scenic Berkshire hills, with equipment rental available.
  • Clarks Pond: Outdoor ice skating north of Boston with adjacent parking. Check ice safety with city hall before going.
  • Berkshire East Mountain Resort: Features popular skiing trails in the Berkshires suitable for all skill levels.
  • Hilltop Orchards: Offers cross-country skiing with lessons and rentals, plus a cozy Barrel Room for relaxing and enjoying apple wine.
  • Nashoba Valley Ski Area: Known for skiing and snow tubing with specific lanes designated for tubing. Open seven days a week during the season.
  • Walden Pond State Reservation: Provides a flat, 1.7-mile trail for snow-shoeing, suitable for beginners and children.
  • Ski Ward Ski Area: Features eight lanes and two lifts for snow tubing, with over 200 tubes available for rent.
  • Maple Corner Farm: A historic working farm offering snow-shoeing and cross-country skiing on over six miles of marked trails, complete with a cozy fire and snack bar for warming up.
  • Hot Stories
    Select a Massachusetts town to find
    the Best Things To Do and Places To Go around you