Long Trail: Southern Terminus via the Appalachian Trail
A common approach to the southern terminus of Vermont's Long Trail.
Moderate Hiking
- Distance
- 6.3 km
- Ascent
- 538 m
- Descent
- 21 m
Hiking in Massachusetts
Go hiking in Massachusetts with curated guides of the best hikes across the region. With over 53 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 hiking trail recommendation in Massachusetts from one of our 2 guidebooks, or get inspired by the 53 local adventures uploaded by the FATMAP community. Start exploring now!
Hiking Routes in Massachusetts
Long Trail: Massachusetts State Line to Stratton Pond
The southernmost segment of Vermont's Long Trail.
Difficult Hiking
- Distance
- 55 km
- Ascent
- 2.3 km
- Descent
- 2.4 km
Appalachian Trail: MA-2 to Stratton Pond
The AT transitions from the Berkshires of Massachusetts to the Green Mountains of Vermont.
Difficult Hiking
- Distance
- 61 km
- Ascent
- 2.8 km
- Descent
- 2.3 km
Appalachian Trail: US-20 to MA-2
The AT traverses the largest state forest to the highest summit in Massachusetts.
Difficult Hiking
- Distance
- 65 km
- Ascent
- 2.3 km
- Descent
- 2.5 km
Appalachian Trail: Salisbury to US-20
The first half of Massachusetts, widely renowned for Mount Everett and Guilder Pond.
Difficult Hiking
- Distance
- 76 km
- Ascent
- 3.1 km
- Descent
- 2.9 km
Cape Cod Rail Trail
A beautiful paved path running through the Cape Cod countryside.
Easy Hiking
- Distance
- 37 km
- Ascent
- 215 m
- Descent
- 211 m
Dogtown woods loop from Natti Woods (shortened)
Loop from Natti Woods, through Dogtown, up to Steel Derrick Quarry and back
Moderate Hiking
- Distance
- 13 km
- Ascent
- 179 m
- Descent
- 179 m
Stupid Trail to Haskell Pond and Fishbone Loop
Loop trail from Aggasiz Rock to Haskell Pond and Fishbone Trail
Difficult Hiking
- Distance
- 14 km
- Ascent
- 289 m
- Descent
- 289 m
Hiking Guidebooks in Massachusetts
58 routes · Hiking
The Appalachian Trail
9 routes · Hiking