Skip to content

Loop Trails in Massachusetts

The directory currently contains 63 quality-checked routes matching this guide in Massachusetts. Their average mapped distance is 3.8 km and average recorded ascent is 72 m (236 ft); the longest route in the set is 35.7 km.

This subset represents 21% of the 300 quality-checked routes in Massachusetts. Its average distance is 3.8 km, compared with 9.0 km across the full local set. Average recorded ascent is 72 m (236 ft), versus 124 m (407 ft) for all quality-checked routes in the same area.

Every route in this set is classified as a loop and returns to its starting area. A loop can still reuse part of the same path. Within this set, 43 routes (68%) are rated easy, 2 (3%) are rated hard or expert, and 63 (100%) are recorded as loops. Ratings are computed from available distance and elevation data and do not establish current terrain or access.

Data refreshed September 2026

Trails

Moderate

Watatic Summit

Massachusetts · United States

Distance
5.3 km
/ 3.3 mi
Elevation gain
246 m
Typical duration
1 hr 29 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
A man fishing in the Indian Head River reservoir , on the border of Pembroke and Hanson in Massachusetts.
Easy

Indian Head River Trail

Massachusetts · United States

Distance
5.6 km
/ 3.5 mi
Elevation gain
48 m
Typical duration
1 hr 14 min
  • River
  • Waymarked route
Easy

Woodland Path Loop

Massachusetts · United States

Distance
1.0 km
/ 0.6 mi
Elevation gain
16 m
Typical duration
14 min
  • Forest
  • Waymarked route
Westward view from Thatcher Ledges
Expert

Tully Trail

Massachusetts · United States

Distance
35.7 km
/ 22.2 mi
Elevation gain
684 m
Typical duration
9 hr 6 min
  • Mountain
Moderate

Reservoir Trail

Massachusetts · United States

Distance
9.5 km
/ 5.9 mi
Elevation gain
135 m
Typical duration
2 hr 11 min
  • Waymarked route
Moderate

Rock Circuit Trail

Massachusetts · United States

Distance
6.5 km
/ 4.1 mi
Elevation gain
147 m
Typical duration
1 hr 35 min
  • Waymarked route
Moderate

Skyline Trail

Massachusetts · United States

Distance
11.8 km
/ 7.3 mi
Elevation gain
230 m
Typical duration
2 hr 48 min
  • Waymarked route
Vestigial railroad tracks along side the w:Minuteman Bikeway in Lexington, Massachusetts.
Moderate

ACROSS Lexington Route A

Massachusetts · United States

Distance
8.4 km
/ 5.3 mi
Elevation gain
23 m
Typical duration
1 hr 48 min
  • Waymarked route
Easy

Pond Passage Loop

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
13 m
Typical duration
23 min
  • Waymarked route
Easy

Long Lake Loop

Massachusetts · United States

Distance
3.0 km
/ 1.9 mi
Elevation gain
67 m
Typical duration
44 min
  • Lake
Easy

Yellow Loop

Massachusetts · United States

Distance
3.6 km
/ 2.3 mi
Elevation gain
80 m
Typical duration
53 min
  • Waymarked route
Easy

Lower Vine Brook Loop

Massachusetts · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
10 m
Typical duration
15 min
  • River
Hard

Thoreau’s Footsteps

Massachusetts · United States

Distance
13.0 km
/ 8.1 mi
Elevation gain
705 m
Typical duration
3 hr 46 min
Easy

Pegan Cove

Massachusetts · United States

Distance
0.6 km
/ 0.4 mi
Typical duration
7 min
  • Waymarked route
Easy

blue trail

Massachusetts · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
6 min
  • Waymarked route
Moderate

BoundaryTrail

Massachusetts · United States

Distance
5.4 km
/ 3.3 mi
Elevation gain
125 m
Typical duration
1 hr 18 min
Moderate

Cat Rock Loop

Massachusetts · United States

Distance
4.1 km
/ 2.6 mi
Elevation gain
80 m
Typical duration
59 min
Easy

Interior Loop Trail

Massachusetts · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
45 m
Typical duration
24 min
Easy

Barretts Mill Loop

Massachusetts · United States

Distance
1.9 km
/ 1.2 mi
Typical duration
24 min
Easy

Russell Trail

Massachusetts · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
6 m
Typical duration
19 min
Easy

South Loop Trail

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
25 m
Typical duration
24 min
Easy

Lookout Trail Loop

Massachusetts · United States

Distance
1.4 km
/ 0.9 mi
Elevation gain
42 m
Typical duration
21 min
  • Panoramic viewpoint
  • Waymarked route
Easy

Outer Loop

Massachusetts · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
47 m
Typical duration
23 min
Easy

Page and Sadie Trail

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
20 m
Typical duration
36 min
Moderate

Cascade Loop

Massachusetts · United States

Distance
0.8 km
/ 0.5 mi
Typical duration
10 min
  • Waterfall
  • Waymarked route
Moderate

Stone Cliffs Loop

Massachusetts · United States

Distance
0.9 km
/ 0.5 mi
Elevation gain
33 m
Typical duration
14 min
  • Coastal
  • Waymarked route
A trail on the abandoned right-of-way of the never-used Lancaster Railroad in the Danforth Creek Property in Hudson in May 2017
Moderate

Danforth Loop

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
61 m
Typical duration
27 min
Easy

Buttonbush Trail

Massachusetts · United States

Distance
0.4 km
/ 0.3 mi
Elevation gain
6 m
Typical duration
6 min
Easy

Magnolia Trail

Massachusetts · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
11 m
Typical duration
7 min
Three Sisters of Nauset (Twin Lights)
Easy

Nauset Marsh Trail

Massachusetts · United States

Distance
1.9 km
/ 1.1 mi
Elevation gain
14 m
Typical duration
24 min
Easy

Red Route

Massachusetts · United States

Distance
0.5 km
/ 0.3 mi
Elevation gain
8 m
Typical duration
6 min
Moderate

Charcol Trail

Massachusetts · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
160 m
Typical duration
50 min
Moderate

Blue Trail

Massachusetts · United States

Distance
3.2 km
/ 2.0 mi
Elevation gain
99 m
Typical duration
49 min
Moderate

Bob's Trail

Massachusetts · United States

Distance
1.9 km
/ 1.2 mi
Elevation gain
109 m
Typical duration
34 min
  • Waymarked route
One lane bridge over Millers River
Moderate

Farley Ledge loop

Massachusetts · United States

Distance
2.9 km
/ 1.8 mi
Elevation gain
223 m
Typical duration
57 min
  • Waymarked route
Moderate

Whale Rock Loop

Massachusetts · United States

Distance
0.7 km
/ 0.4 mi
Elevation gain
36 m
Typical duration
12 min
  • Waymarked route
Easy

Hammertown Loop

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
62 m
Typical duration
40 min
Easy

Alan Emmet Trail

Massachusetts · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
13 m
Typical duration
27 min

The shortlist, side by side

The ten highest scoring routes on this page, so you can compare effort before opening any of them.

Distance, ascent, walking time and difficulty for the top routes
RouteDistanceAscentTimeDifficultyBest season
Watatic SummitMassachusetts5.3 km246 m1 hr 29 minModerateApril to October
Indian Head River TrailMassachusetts5.6 km48 m1 hr 14 minEasyApril to October
Great Meadows Bird Observer TrailMassachusetts4.7 km0 m59 minEasyApril to October
Woodland Path LoopMassachusetts1.0 km16 m14 minEasyApril to October
Tully TrailMassachusetts35.7 km684 m9 hr 6 minExpertApril to October
Reservoir TrailMassachusetts9.5 km135 m2 hr 11 minModerateApril to October
Rock Circuit TrailMassachusetts6.5 km147 m1 hr 35 minModerateApril to October
Skyline TrailMassachusetts11.8 km230 m2 hr 48 minModerateApril to October
ACROSS Lexington Route AMassachusetts8.4 km23 m1 hr 48 minModerateApril to October
ALC ACROSS Lexington Route CMassachusetts4.1 km12 m52 minEasyApril to October

Watatic Summit, Indian Head River Trail, Woodland Path Loop currently rank highest in this filtered set according to the directory score. Open an individual route to inspect its mapped line, elevation profile, data source and planning caveats. Check live access, conditions and local rules with an official source before travelling.

Frequently asked questions

Related guides

Other shortlists covering the same area or the same kind of terrain.

People also search for