Winter walk in the Public Garden. Photo courtesy of Massachusetts Office of Travel & Tourism
Winter walk in the Public Garden. Photo courtesy of Massachusetts Office of Travel & Tourism

Where to Take Wonderful Wintertime Walks with Boston Kids

Boston winters can feel really long, especially when you and the kids have been cooped up inside too much. One of my favorite ways to shake off a case of cabin fever is to bundle up and head outside for a winter walk (another favorite is ice skating). Taking a stroll on the first snowy day is an annual tradition in my house—followed by a cup of hot cocoa, of course. We extend the winter walking season as long as we can, sometimes with the help of snow shoes, at these favorite winter walking destinations in the Boston area.

Somerville Community Path: I walk on the Somerville Community Path, which now runs from Lowell Street through Davis Square, nearly every day of year. It’s spectacular any time of year, a true respite from busy city life, but it really shines in winter. Even last year when snow was piled 10-feet-high, the path was clear and walking on it was like being in a winter wonderland. Since one end of the path is in Davis, consider stopping for lunch or hot chocolate mid-walk to warm up.

Minuteman Bikeway: This 10-mile paved multi-use trail runs from the Alewife MBTA Station in North Cambridge through Arlington and Lexington to Bedford. There are many access points, making the path easy to find no matter which town you’re in, and the trail’s paved surface makes it the perfect place to take a winter stroll when you’re itching to get outside. As with the Community Path, the Minuteman goes right through several downtowns, which have nice places for hot chocolate or a lunch break.

Boston Common and Public Garden: Beautiful in any season, a walk through the Boston Common and Public Garden is extra lovely in winter. Snow tends to make the city seem quieter than usual, so you might even feel like you have the place to yourselves. Stop by the “Make Way for Ducklings” statue for a winter portrait you’re sure to cherish.

The Esplanade: On either side of the Charles River runs a paved path that’s a great destination for a winter walk. Whether you’re in Boston or Cambridge you’ll enjoy spectacular views of the other city from the path and can even-pit stop at the Museum of Science, which sits along the path, for a little indoor exploration.

Fresh Pond: The ever-changing landscape at Fresh Pond Reservation in Cambridge makes it a fun walking destination in any season. Do a loop of the pond in winter to stretch your legs and get some much-needed fresh air. It’s so scenic, it’s almost hard to believe how close to the city you are when you're at the pond.

Walden Pond: Located in Concord, Walden Pond is a favorite destination in the summer, but you can walk the peaceful trail that surrounds the pond in winter as well. If it hasn’t been too snowy, boots should do the trick, but if the snow is piling up, better take along some snowshoes.

Middlesex Fells Reservation: Just north of Boston, the Middlesex Fells Reservation straddles Malden, Medford, Melrose, Stoneham and Winchester, and includes trails for all ability levels. There’s plenty of parking, especially if you start at Sheepfold, which is also a popular dog play area. As with Walden, if the snow is light, boots should be fine, otherwise, bring snowshoes.

Blue Hills Reservation: Just South of Boston, Blue Hills Reservation straddles Milton, Quincy Braintree, Canton, Randolph and Dedham, and includes trails for all ability levels. For kids and hikers with special needs, the trail connected to the Blue Hills Trailside Museum is especially nice. Boots will be fine in light snow, but snowshoes are recommended for deeper snow. Some areas are even popular with cross-country skiers.

Top image from a winter walk on the Somerville Community Path

Somerville Community Path
Davis Square
Somerville, MA 02144

Minuteman Bikeway
Alewife Station
North Cambridge, MA 02140

Boston Common and Public Garden
139 Tremont St.
Boston, MA 02116

Esplanade (Museum of Science)
1 Science Park
Boston, MA 02114

Fresh Pond Reservation
250 Fresh Pond Parkway
Cambridge, MA 02138

Walden Pond
915 Walden St.
Concord, MA 01742

Middlesex Fells Reservation
Stoneham, MA 02180

Blue Hills Reservation
695 Hillside St.
Milton, MA 02186
"Go Out Doors" Exhibit
Bruce Freeman Rail Trail - 8:00 AM
Santa's Wonderland
Bass Pro Shops - various times
A Band of Angels
Online - various times
The Polar Express 4-D Experience
Museum of Science - various times
She Persisted, The Musical
Streaming - various times
Neighborhood Guides
Activity Guides