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Explore the Best Trails in Massachusetts: Scenic Views and Peak Adventures
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items This guide invites hikers of all levels to discover the state's most breathtaking trails, from coastal paths to mountainous peaks.
One of the most famous long-distance hiking trails in the U.S., passing through western Massachusetts.
Appalachian Trail – Lanesborough, MA
A scenic 12.7-mile paved trail that runs along a former railroad corridor, perfect for biking and walking.
Ashuwillticook Rail Trail – Lanesborough, MA
A 25-mile paved trail that takes you through the heart of Cape Cod, ideal for biking, walking, and rollerblading.
Cape Cod Rail Trail – Brewster, MA
This 22-mile trail follows an old railroad bed and is suitable for hiking, biking, and horseback riding.
Southern New England Trunkline Trail – Franklin to Douglas, MA
Over 125 miles of trails offering hiking with scenic views of Boston and the surrounding landscape.
Blue Hills Reservation Trails – Milton, MA
A 92-mile trail running from Rhode Island to New Hampshire, offering diverse terrain for hikers.
Midstate Trail – Worcester County, MA
A 230-mile trail that loops around Greater Boston through forests, wetlands, and historic sites.
Bay Circuit Trail – Eastern Massachusetts
A rugged 114-mile trail that runs from the Connecticut border to the New Hampshire border.
Metacomet-Monadnock Trail (M&M) – Western Massachusetts
A 22-mile loop trail offering views of waterfalls, lakes, and forests in central Massachusetts.
Tully Trail – North Quabbin Region
A 47-mile trail named after the poet Robert Frost, running through scenic areas in western Massachusetts.
Robert Frost Trail – Pioneer Valley
This 2.6-mile out-and-back trail offers a moderate hike with rewarding summit views. Mount Watatic is part of the Wapack Range and provides stunning vistas of the surrounding landscape, including views of Mount Monadnock in New Hampshire
Mount Watatic Trail – Ashburnham, MA
Stretching up to 15 miles one-way, this trail offers panoramic views of the Connecticut River Valley. It’s a great option for hikers looking for a mix of forested paths and scenic ridgeline views
Pocumtuck Ridge Trail – Deerfield, MA
With over 30 miles of trails, this 2,200-acre municipal forest park offers hiking, mountain biking, and horseback riding. Highlights include Dungeon Rock—a cave with pirate lore—and scenic reservoirs
Lynn Woods Reservation – Lynn, MA
This 6.9-mile loop trail is known for its rocky terrain and spectacular views of the Boston skyline. It’s a challenging hike that rewards adventurers with sweeping vistas from several high points along the trail
Skyline Trail (Middlesex Fells Reservation) – Stoneham, MA
Explore 12 miles of interconnecting trails that wind through forests, wetlands, and meadows. The sanctuary is perfect for birdwatching and wildlife observation, with scenic boardwalks and an observation tower
Mass Audubon's Ipswich River Wildlife Sanctuary
The highest point east of the Connecticut River, this area offers several trails with varying difficulty levels. The Harrington Trail provides rewarding vistas of the Wachusett Reservoir
Wachusett Mountain
This area includes over 100 miles of trails across 2,575 acres. The Skyline Trail is particularly famous for its views of the Boston skyline.
Skyline Trail - Massachusetts
The highest point east of the Connecticut River, this area offers several trails with varying difficulty levels. The Harrington Trail provides rewarding vistas of the Wachusett Reservoir.
Wachusett Mountain via Harrington Trail