Best Massachusetts Hiking Trails

Massachusetts has 36 hikes.

Located in the US, the hiking in Massachusetts offers over thirty trail routes from which to choose. The best Massachusetts hiking based on popularity are considered to be Appalachian Trail, Riga Plateau, South Taconic Trail, Erving State Forest, and October State Forest. For a detailed trail description and printable trailhead map, just select a Massachusetts hiking trail below.


Erving State Forest

East of Greenfield near Erving, the 4,500 acre Erving State Forest has miles of trails shared by hikers and bikers. The Forest is on the dividing line between Northern and Southern New England forests cultures thus producing high foliage diversity.  MORE INFO

Myles Standish State Forest

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.  MORE INFO

Wompatuck State Park

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.  MORE INFO

Great Island Trail

West of Wellfleet, the Great Island Trail is a 6.8 mile round trip hike through dunes, salt marshes and pine forests over to Great Island. There are two side hikes: a 1.4 mile hike to the old Tavern site, and a 2 mile out-and-back to Jeremy Point, which is submerged at high tide.  MORE INFO

Cape Cod Trail

The Cape Cod Rail Trail is a 27 mile hiking route from SR134 in Dennis to Le Count Hollow Road in Wellfleet. The hiking route passes by salt marshes, cranberry bogs and ponds. It connects with multi-purpose paths into Nickerson State Park and Cape Cod National Seashore.  MORE INFO

Harold Parker State Forest

Near North Andover, the 3,500 acre Harold Parker State Forest has a nice section of the Bay Circuit Trail rolling hikers through maple and oak forest, low lying swampy areas, and rock outcropings. This forest can be quite moist and lush during the summer producing a bumper crop of mosquitos - so bring lots of repellant.  MORE INFO

Chester-Blandford State Forest

Near Chester in the Berkshires, the 2,300 acre Chester-Blandford State Forest has miles of trails. These hiking trails are also shared with horseback riders and mountain bikers. Don't miss the scenic Sanderson Brook Falls  MORE INFO

Harold Parker State Forest

Near North Andover, the 3,500 acre Harold Parker State Forest has miles of trails and 35 miles of logging roads. The hiking trails roll through maple and oak forest, low lying swampy areas, and rock outcropings. A section of the Bay Circuit Trail passes through the forest. This forest can be quite moist and lush during the summer producing a bumper crop of mosquitos - so bring lots of repellant.  MORE INFO

Midstate Trail

Near Rutland, the Midstate Trail is a 92 mile long hiking trail extending from Rhode Island to New Hampshire along the rolling hills of centrall Massachusetts. At the New Hampshire border, the trail connects with the Wapack Trail.  MORE INFO

Willowdale State Forest

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.  MORE INFO

Metacomet-Monadnock Trail

Near Lenox, the Metacomet-Monadnock Trail is a 117 mile foot path from Connecticut to Mt. Monadnock in New Hampshire. It is maintained by the Berkshire chapter of the Appalachian Mountain club and other volunteers. The trail follows a corridor of elevated wildland from the basalt ridges of northern Connecticut clear through central Massachusetts to a dramatic finale on the craggy summit of 3,113-foot Mt. Monadnock.  MORE INFO

F. Gilbert Hills State Forest

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.  MORE INFO

Douglas State Forest

South of Worcester on the tri-state border, the 4,600 acre Douglas State Forest has 30+ miles of trails and jeep roads. The forest is on a plateau with no major hills and a total elevation variation of around 300 feet. Many of the trails are very rocky and luckily, they connect with several double-tracks and gravel forest roads.  MORE INFO

Blue Hills Reservation

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.  MORE INFO

Lynn Woods Reservation

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).  MORE INFO

Wellfleet Bay Wildlife Sanctuary

North of Eastham and southwest of Wellfleet, the Wellfleet Bay Wildlife Sanctuary has a trail system totaling 5 miles through pine forest and salt marshes. The three larger loops worth trying are the Try Island Trail, Bay View Trail and the Goose Pond Trail.  MORE INFO

West Barnstable Conservation Area

West of Barnstable and northwest of Hyannis on Cape Cod, the Trail Of Tears is a 16 mile hiking trail network through the woodlands of the 1,100 acre West Barnstable Conservation Area. The forest is a mixture of pine and oak, along with small amounts of fir and other tree species. This network follows the Barnstable powerlines down to the Sandwich border at Chase Road.  MORE INFO

Breakheart Reservation

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.  MORE INFO

Nickerson State Park

East of Brewster and west of Orleans, the 1,900 acre Nickerson State Park has a variety of hiking trails. There is the 1 mile loop around Flax Pond, the 1 mile loop around Little Cliff Pond, the 3 mile loop around Cliff Pond and also access to the Namskaket Sea Path along Cape Cod Bay.  MORE INFO