Boston Trails

Boston's Best Local Hikes

We've got your picks for the best after work, day-long, and overnight trips near Beantown, including the White Mountains, Blue Hills, and more.

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Get the view from Mt. Morgan on one of Boston’s best local hikes, an overnight on the Squam Range Traverse. Photo by John Welch

boston's best local hikes
Photo by John Welch

After Work

Crystal Spring Trail, Middlesex Fells Reservation

Unless you live in Dot or Southie, going north to the Fells makes for a quicker woodsy escape than heading to Milton. Ramble along the easy, 1.4-mile Crystal Spring Trail loop, which begins by the eastern shore of Spot Pond. Skirt the summit of 78-foot Whip Hill where dogwoods flower in spring, and turn blaze orange come fall. End back on Wyoming Ave. (2 miles north of the Orange Line Oak Grove stop).

Trailhead42.458136, -71.087766Drive time 20 mins.


Skyline Trail, Blue Hills Reservation

The deepest woods close to Boston lie in the Blue Hills, and this 11.6-mile out-and-back rolls up and down them. From the Trailside Museum, climb west on the Coon Hollow Path (use the left branch). Grab the Skyline Trail atop Great Blue Hill (635 feet), and travel over Chickatawbut, Fenno, Kitchamakin, and Nahanton Hills, with views over the Harbor. Turn around there.

Trailhead42.216043, -71.119201 Drive time 30 mins.


Squam Range Traverse, White Mountain NF

Bostonians know the best hiking around is beyond the state liquor stores up north. But this route is neither as far as the Presidentials, nor as hard on the legs. That doesn’t mean easy: This 11.9-mile (one way) slice of the Squam Range starts on Sandwich Notch Road and heads south, hitting Mt. Squam, East Doublehead, Mt. Percival, Mt. Morgan, Mt. Webster, Mt. Livermore, and Cotton Mountain—five stand taller than 2,000 feet. Drop off Mt. Percival for water. End at NH 113.

Trailhead43.828800, -71.501040Drive time 2 hrs. 15 mins.


Hilton’s Tent City has occupied a four-story spot on Friend Street (near the Garden) and has been dispensing gear tips and trail advice since 1942.

See the rest of the country’s best local hikes

best local hikes