Jamaica Pond Path
Stroll around a community focal point and enjoy its flora and fauna
Easy Hiking
- Distance
- 2.3 km
- Ascent
- 8 m
- Descent
- 8 m
Massachusetts
Explore Massachusetts with curated guides of the best hiking trails, trail running routes, and more. With over 98 3D trail maps in FATMAP, you can easily discover and navigate the best trails in Massachusetts.
No matter what your next adventure has in store, you can find a guide on FATMAP to help you plan your next epic trip.
Get a top trail recommendation in Massachusetts from one of our 2 guidebooks, or get inspired by the 98 local adventures uploaded by the FATMAP community. Start exploring now!
Routes in Massachusetts
East Boston Memorial Park to Piers Park
An excellent hike combining a fix of nature and some exceptional city views
Easy Hiking
- Distance
- 4 km
- Ascent
- 13 m
- Descent
- 13 m
Bremen Street Park & East Boston Memorial Park
Wander around 2 of Boston's finest parks in one loop
Easy Hiking
- Distance
- 2.8 km
- Ascent
- 8 m
- Descent
- 8 m
Constitution Beach
A gentle stroll along an urban beach
Moderate Hiking
- Distance
- 1.5 km
- Ascent
- 3 m
- Descent
- 3 m
Southwest Corridor Path
An easy, paved stroll through a green corridor in downtown Boston
Easy Hiking
- Distance
- 2.4 km
- Ascent
- 1 m
- Descent
- 1 m
Lost Emerald Necklace Trail
A pleasant stroll through a famous Boston park
Easy Hiking
- Distance
- 2.6 km
- Ascent
- 7 m
- Descent
- 7 m
Boston Freedom Trail
A journey through America's past and Boston's present
Easy Hiking
- Distance
- 5.1 km
- Ascent
- 55 m
- Descent
- 41 m
Boston Walking City Trail Stage 4
Charles River to Bunker Hill Monument
Moderate Hiking
- Distance
- 12 km
- Ascent
- 77 m
- Descent
- 54 m
Boston Walking City Trail Stage 3
Jamaica Pool to the Charles River
Moderate Hiking
- Distance
- 9.9 km
- Ascent
- 109 m
- Descent
- 125 m
Boston Walking City Trail Stage 2
Adams Park to Jamaica Pool
Moderate Hiking
- Distance
- 9.4 km
- Ascent
- 155 m
- Descent
- 158 m
Boston Walking City Trail Stage 1
Harvest River Bridge to Adams Park
Moderate Hiking
- Distance
- 13 km
- Ascent
- 142 m
- Descent
- 129 m
Mount Toby and Ox Hill
Hike to the top of two mountains in western mass
Moderate Hiking
- Distance
- 5.3 km
- Ascent
- 300 m
- Descent
- 300 m
Sand Dune Trail
The best sand dunes hike in Massachusetts.
Moderate Hiking
- Distance
- 3.1 km
- Ascent
- 60 m
- Descent
- 60 m
Mohawk Trail State Forest Campground Loop and Todd Mountain
Climb Todd Mountain and loop around the mountain's base on the Mahican-Mohawk Trail.
Moderate Hiking
- Distance
- 6.2 km
- Ascent
- 366 m
- Descent
- 366 m
Ox Hill, Mount Toby, and Roaring Mountain Loop
Loop to the top of 3 peaks in western mass
Moderate Hiking
- Distance
- 7.8 km
- Ascent
- 436 m
- Descent
- 436 m
Mount Sugarloaf (MA)
Hike up mount sugarloaf
Easy Hiking
- Distance
- 4.7 km
- Ascent
- 203 m
- Descent
- 203 m