Roamward

Hikes · Massachusetts

Best hikes in Massachusetts.

Massachusetts hiking is the Berkshires and traprock ridges — Greylocks summit, Monument Mountain, and Bash Bish Falls.

Curated trails5
Distance range1.5–6.6 mi
Biggest climb1,900 ft
Difficulty2 easy · 2 moderate · 1 hard
TerrainBerkshire summits & traprock cliffs
Best seasonSummer & fall (foliage)
Don’t missMount Greylock

Boots on

5 hikes worth the detour.

Sorted easy to expert. Every one mapped with distance, route type, and elevation gain — built for everyone from the RV & camping crew to the bucket-list crowd.

Bash Bish Falls

Easy · 1.5 mi · Out & back · 300 ft

the tallest single-drop falls in the state

Halibut Point

Easy · 1.5 mi · Loop · 50 ft

a granite-quarry coast walk on Cape Ann

Monument Mountain

Moderate · 3 mi · Loop · 700 ft

a Berkshire quartzite ridge

Mount Tom (Holyoke Range)

Moderate · 5 mi · Loop · 1,000 ft

traprock cliffs over the Pioneer Valley

Mount Greylock

Hard · 6.6 mi · Out & back · 1,900 ft

the state high point, with a war-memorial tower

Know a Massachusetts trail we’re missing?

Plan the Massachusetts trip

Hikes, gems, scenic drives — all in one Massachusetts guide.

See everything worth the detour in Massachusetts, then let Roamward build the trip around it. Know a Massachusetts trail we’re missing? Add it — we’re building this with the people who actually hike it.

No spam. Just beta timing and launch notes.

Full Massachusetts guide →All states