The Commonwealth Blog

Monday, December 18, 2017

Best Outdoor Winter Activities in Massachusetts

Massachusetts residents are no strangers to harsh winters. But just because there’s snow on the ground doesn’t mean we’re going to stay indoors all season. The upside of living somewhere with cold, snowy winters is that we get to enjoy some of the best outdoor activities in the country. Check out some of our favorite things to do during the winter.

Ice Skating

There’s probably no winter activity more iconic than ice skating on a frozen pond. Fortunately, Massachusetts has plenty of outdoor spots where you can strap on your skates. Boston Common Frog Pond is a go-to for many residents of the greater Boston area. It’s $6 for a skating pass (and free for kids under 58 inches), and you can also rent skates if you don’t have your own.

For an inexpensive skating trip, Kelly Outdoor Rink in the Jamaica Plain neighborhood of Boston is another great bet. Skate rentals are only $2, and those who are inexperienced on the ice can take lessons on Saturdays.


Massachusetts has sledding slopes for everyone, from the youngest toboggan riders to the older thrill-seekers. Boston Common and the Sugar Bowl near Jamaica Pond both offer some gentle slopes and obstacle-free space that’s perfect for young sledders. The Sugar Bowl also gives sledders the chance to build up enough momentum going down one side to slide back up the other.

For those who are looking for steep inclines and fast-paced sledding, Hospital Hill in Northampton is a good option. Prospect Hill Park in Waltham also has some big slopes and breathtaking views of the surrounding area.

Downhill Skiing and Snowboarding

New England is known for its exceptional skiing, and you don’t even have to leave Massachusetts to discover exciting new trails. Nashoba Valley Ski Area in Westford, Massachusetts boasts 17 trails and lifts that carry skiers and snowboarders 240 vertical feet up the mountain. For those who would rather not strap boards to their feet, Nashoba Valley also has a large snow tubing park.

Ski Butternut in Great Barrington is another in-state ski resort popular with families and beginner skiers and snowboarders. 20 percent of the terrain is rated for beginners while 60 percent is rated as intermediate, meaning that no one has to face a black diamond slope before they’re ready.

Skiers and snowboarders looking for challenges for all ability levels should visit Mount Wachusett, just an hour’s drive from Boston in Princeton, Massachusetts. The resort has 26 trails, a 2006-foot summit, and a mile and a half long trail on Balance Rock.

Cross-Country Skiing and Snowshoeing

If you’re hoping to get a bit more of a cardio workout than you would with downhill skiing, there are also plenty of places to go snowshoeing or cross-country skiing in Massachusetts. Just 15 miles outside of Boston, the Weston Ski Track offers a 2K lighted loop. That means that the short days of winter won’t stop you from skiing: your trail will be illuminated no matter when you go.

Feeling competitive? Hilltop Orchards in Richmond, MA hosts 5K snowshoeing and cross-country ski races throughout the winter. If you need any more motivation to check it out, Hilltop Orchards also has a winery on its grounds. Get a workout and then reward yourself with a wine tasting.

Gathering for a Winter Bonfire

Not every outdoor winter activity in Massachusetts has to involve a workout: if you’re looking for a way to relax outside without getting too cold, just head to a bonfire. Several Massachusetts cities, including Newbury and Salem, host big Christmas tree bonfires where residents are invited to burn their trees once the holidays are over. Going to a bonfire is a lot like gathering in front of a giant fireplace, with all your friends and neighbors around you. What’s not to love?

Loading Property Compare
Perfect Fit Buyer Registration
Request a Home Evaluation

Mobile Search

Use any internet enabled phone to search every home for sale in our area! More

Homes Like Mine

Find the approximate value of your home by comparing your home’s criteria to homes that are currently for sale.


Home Updates


This Week

Open Houses 2299 New Listings 1506 Bank Owned 735

These Listings Updated Daily

Boston Real Estate by City

Berkshire Hathaway HomeServices Commonwealth Real Estate | 12 Huron Drive, Natick, MA 01760 | Phone: (508) 810-0700

© 2019 BHH Affiliates, LLC. An independently operated subsidiary of HomeServices of America, Inc., a Berkshire Hathaway affiliate, and a franchisee of BHH Affiliates, LLC.
Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of HomeServices of America, Inc.® Equal Housing Opportunity.
Information not verified or guaranteed. If your home is currently listed with a Broker, this is not intended as a solicitation.

Terms of Use/Privacy Policy | Agents Only | Library
Built and powered by Constellation Web Solutions