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Places to Hike Within Minutes of Boston

Hit the Trails at These Four Local Favorites for Hiking


While a trip to the mountains of Vermont, New Hampshire, Maine, and Western Mass. can provide a surreal weekend hiking experience, there are a number of worthwhile trails to utilize minutes from Boston, most providing spectacular city views. Here are four favorite places and ways to enjoy a hike just a short drive from the city, yet they are trails that provide instant getaways.

1. Boston Harborwalk

deer island boston
Photo by Eric Wilbur
Nearly 50 miles of waterfront trails stretch from Dorchester to Charlestown, providing dramatically different views of Boston Harbor. Each neighborhood possesses distinct characteristics, making the walk a nice way to visit parts of the city you may not be familiar with. Two of the best stretches of the walk are in South Boston and Deer Island. The South Boston stretch includes popular Castle Island, the historic home of Fort Independence. On Deer Island – known mainly for its wastewater treatment facility – you’ll find rolling hills, harbor views, and a dramatic skyline scene. It’s a perfect place to bring a picnic and enjoy an afternoon escape just miles from downtown.

2. Blue Hills Reservation

Some of the more strenuous hikes in the Boston area can be found in Canton at the Blue Hills Reservation, which features 125 miles of trails, ranging in difficulty. A big favorite with locals is the Skyline Trail, a 4 1/2-mile loop that boasts spectacular views of the Boston skyline from the highest points of the hike. The trail features both casual and rocky terrain, so be sure that all members of your party are able to handle the strenuous aspects of the hike. Otherwise, a more docile trail such as Fowl Meadow, a flatter way to enjoy the surroundings. For more ideas, pick up a map at the Blue Hills Reservation headquarters or the trailside museum.

3. Middlesex Falls Reservation

The serene Middlesex Falls Reservation is just minutes north of the city. Located in Medford, the reservation offers the opportunity for both mature walks and educational programs throughout the year. The most popular hike here is the Skyline Trail, a challenging seven-mile loop that brings hikers through deep woods, rocky ledges, and various ascents and descents. The hike also provides a dramatic view of the city from Wright’s Tower. The Skyline may be about as strenuous a hike as one can expect in the Boston area.

4. Spectacle Island

Take the ferry into the Boston Harbor Islands, and make a stop at Spectacle Island, arguably the chain’s shining jewel. The hiking paths here provide a serene surrounding in which to walk, picnic, or simply just relax on the beach with a book. Ferries generally leave on the hour, depending on the time of year. Round-trip tickets are $14 for adults, $8 children ages 3-11.
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