5 Outdoor Adventures in Greater Boston

Boston is a four season city, with all sorts of wonderful things to do outdoors. This list of popular outdoor activities in Boston include both urban and suburban venues, like parks, playgrounds, walking trails, water activities and more. Get outside!

Charles River Esplanade

Catch scenic views of the Charles River when you walk along this three-mile Charles River Esplanade in the heart of Boston. Starting at the Museum of Science and ending at the Boston University Bridge, the Esplanade has well-maintained paths for walking, jogging, and biking, along with boat and kayak rentals, public art installations, and many festivals and events throughout the year.

Boston Freedom Trail

If you love American history, the Freedom Trail will take you along 16 historic sites in 2.5 miles. These sites include burying grounds, churches, meeting houses, Paul Revere’s house, Faneuil Hall, and the USS Constitution. Even if you’re not a history buff, you may still enjoy the walk through Boston’s most iconic sites. Faneuil Hall, for instance, was a town meeting place and is now a modern-day food court and shopping center.

Middlesex Fells

One popular hiking destination is Middlesex Fells, which has a network of trails, ponds, and lakes. The Skyline Trail at Middlesex is also heavily trafficked, but is a bit more challenging at 8 miles and 1,000 ft of gain.

Most of the trail is in the woods and doesn’t offer great views, but the there is a section towards the end of the trail with a clear view of the city. If you only want the views but not the workout, park at the South Border Road Parking Lot and take a short hike to Wright’s Tower. Parking here does fill up fast, so go earlier on the weekends. The trail can get icy in the winter as well, so bring some traction!

Spectacle Island

Spectacle Island is a 20-minute ferry ride outside of Boston and offers stunning views of the Boston Skyline, along with a sandy beach and peaceful walking trails. The island was named for its unique shape, which resembles a pair of eyeglasses or spectacles. Head to this open island for sunbathing, picnicking, and second-to-none views of the Boston Harbor and skyline. Be sure to bring some umbrellas for your group, as there is very little shade on the island.

Whale Watching

There’s something unique about seeing such a massive creature in its natural habitat. The Boston Harbor Cruises offer a whale watching tour with naturalists on board to teach you about the animals and make sure the boat isn’t disturbing the whales (the tour is Whale SENSE certified for responsible practices).

According to reviews, tours can take 4 hours, with a lot of that time spent traveling to feeding sites—so make sure to plan for a long day!