Massachusetts Trails

A tall, light gray stone memorial tower rising against a bright blue sky with wispy clouds. The tower features a slightly flared base, narrow rectangular windows near its peak, and is crowned with a large, decorative glass globe beacon. It stands prominently on a lush, green grassy hill surrounded by clusters of dark evergreen trees, while a narrow dirt path in the foreground leads toward a partially obscured wooden picnic table on the right.
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Trail Reviews by Region
See our latest trails from each region. Follow Trailspotting as we explore the state and add more trail reviews.

•  Central Massachusetts
•  Greater Boston
•  Metro West Boston
•  Northeast Massachusetts
•  Western Massachusetts
•  Southeast and Cape Cod

Rail Trail Map
See our separate map of the state's rail trails, in contect with today's live rail network and long-gone routes of history.

•  Rail Trails of Massachusetts

Hiking Spotlight

A tall, light gray stone memorial tower rising against a bright blue sky with wispy clouds. The tower features a slightly flared base, narrow rectangular windows near its peak, and is crowned with a large, decorative glass globe beacon. It stands prominently on a lush, green grassy hill surrounded by clusters of dark evergreen trees, while a narrow dirt path in the foreground leads toward a partially obscured wooden picnic table on the right.
4★ Mount Graylock
3-7 mi · Moderate · Gain 640-2,280 ft
Climb Massachusetts' highest peak, then climb again to the tower viewing platform.

Hiker on a boardwalk above a swamp, surrounded by mist.
4★ Mount Sugarloaf
2-4 mi · Easy & Moderate · Gain 460-1,290 ft
Dramatically protruding from Deerfield's landscape, this mountain has experiences for all.

The image shows an individual wearing a red top and dark pants standing in front of a large rock formation. The rock formation consists of several massive boulders with visible cracks and crevices, some large enough to walk through. The ground is covered with fallen leaves, indicating it might be autumn.
4★ Sunderland Caves
2 mi · Easy · Gain 490 ft
An easy woodland stroll on Mt Toby to these cool, dark caves.

A tall, cylindrical stone tower rises from a forest clearing, built from irregularly shaped stones and topped with a small observation deck featuring a white railing and antenna. Surrounding deciduous trees display green and yellow foliage, suggesting early autumn. A picnic table sits nearby, and the clear blue sky adds to the peaceful, scenic atmosphere.
4★ Shelburne Tower
3 mi · Easy · Gain 1,050 ft
Hike Massaemett Mt's western flanks to check out what is possibly the oldest lookout in USA.

Rail Trail Spotlight

The image shows a large, detailed mural of a bird’s head on a wall under a bridge. The bird has prominent orange, black, and white feathers around its eye, rendered with high realism. In front of the mural, an individual is riding a small bicycle, wearing blue attire including a helmet and sunglasses. The cyclist is in motion, as indicated by the blurred wheels.
5★ East Boston Greenway
2 mi ea way · Easy · Low gradient
Sail your bike from the golden sands at Constitution Beach to the piers of Boston Harbor.

The image shows a silver train with blue stripes on the side, stopped at a station platform next to a yellow building with red trim. There are two individuals on bicycles, one in the foreground and one further back, riding alongside the train tracks. The sky is clear and it appears to be a sunny day. This scene captures a moment of daily life where transportation and leisure activities intersect in an urban setting.
4★ Bedford & Concord Trails
3-8 mi ea way · Easy · Low gradient
Two rustic trails departing from the old Bedford Depot buildings.

The image shows an view of a coastal landscape, featuring a curved shoreline with a road running parallel to it. There is a prominent red-roofed lighthouse near the coast, surrounded by greenery and several parked cars. The coastline is dotted with large rocks and boulders, extending into clear blue waters.
5★ Shining Sea Bikeway
11 mi ea way · Easy · Low gradient
Divers views and picturesque coastal surroundings of Cape Cod.

A vibrant red pedestrian bridge with a curved structure spans over a river. The sky is partly cloudy, and the surrounding landscape includes bare trees, suggesting it might be autumn or winter. A person wearing a bright yellow jacket stands on the bridge, facing away from the camera.
4★ Northern Strand
11 mi ea way · Easy · Low gradient ft
Scenic trail for commuters and recreation alike along a safe, smooth asphalt trail.

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