Best Boston Hiking Trails

The Boston area has 8 hiking trails out of the 37 hikes found in Massachusetts.

  October 15, 2018

Located in Massachusetts, the hiking in Boston offers more than a half-dozen beautiful hikes and backpacking trails. The best Boston hiking based on popularity are considered to be Wompatuck State Park, Myles Standish State Forest, F. Gilbert Hills State Forest, Bay Circuit, and Willowdale State Forest. For a detailed trail description and printable trailhead map, just select a Boston hiking trail below.

Where Can I Hike In Boston?

FEATURED:  Myles Standish State Forest

  Boston, Massachusetts

  August 20, 2016

Southeast of Boston and southwest of Plymouth, the 14,600 acre Myles Standish State Forest is laced with hundreds of miles of trails, paths, fire breaks, paved roads and dirt roads. Some of the pathways in the forest actually predate the Pilgrims. Theres also a 22 mile paved multi-purpose trail. The routes roll gently through sandy pine forest.

FEATURED:  Wompatuck State Park

  Boston, Massachusetts

  July 14, 2016

Southeast of Boston and Hingham, the 3,500 acre Wompatuck State Park has miles of hiking trails, plus a 12 mile paved pathway. The rocky and rooty trails of Wompy roll gently through maple and oak forests. A nice place to park is right at the visitor center.

FEATURED:  Willowdale State Forest

  Boston, Massachusetts

  July 2, 2016

West of Ipswich, the 2,400 acre Willowdale State Forest has 40 miles of trails through forest. The main hiking routes are blazed in red and blue. The combined red/blue route is a 7 mile loop. The trails wind through dense maple and oak forest, and are open to mountain bikers as well.

FEATURED:  F. Gilbert Hills State Forest

  Boston, Massachusetts

  July 7, 2016

Southwest of Boston and Foxboro, the 1,000 acre F. Gilbert Hills State Forest has 23 miles of multi-use trails looping through the forest. One of the more popular hiking routes is the long distance Warner Trail that travels through Norfolk County on the way to Rhode Island.

FEATURED:  Blue Hills Reservation

  Boston, Massachusetts

  July 26, 2016

South of Boston near Milton, the Blue Hills Reservation includes 7,000 acres of varied terrain. It ranges from woodlands to marsh to rocky hills. There is an extensive, well-marked and maintained trail system totaling 125 miles with miles of fire road and trail.

FEATURED:  Lynn Woods Reservation

  Boston, Massachusetts

  October 15, 2018

North of Boston and west of Lynn, the 2,200 acre Lynn Woods Reservation is a local favorite desitination close to Boston. There are 30 miles of trails through pine forest along wetlands and ponds (including Walden Pond).

FEATURED:  Breakheart Reservation

  Boston, Massachusetts

  August 15, 2016

North of Boston and east of Wakefield in Saugus, the Breakheart Reservation has 5 plus miles of multi-purpose trails. The hiking trails include a 3 mile rolling paved loop with numerous side trails.