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Massachusetts

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582 mi 937 km of trail — 25 Featured Runs

Easy Trails 143 Trails Intermediate Trails 88 Trails Hard Trails 14 Trails

Areas Within Massachusetts

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Featured Runs in Massachusetts - 25

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Thoreau's cabin site.

#1

1.8 mi 2.9 km
Walden Pond
 5
Concord, MA
This is from the top of the dam.

#2

4.7 mi 7.6 km
Tully Lake Loop
 1
Royalston, MA
Start of the Pine Trail

#3

3.7 mi 6.0 km
Pine Tree Trail
 1
Pocasset, MA
While unnecessary, this water crossing certainly spiced up the run!

#4

2.9 mi 4.6 km
Outer Loop
 1
Swansea, MA
Experiencing the Old King's Highway seems to bring you back in time.

#5

5.4 mi 8.7 km
Pamet Loop
 1
Truro, MA
Greeting Tree at trailhead.

#6

1.8 mi 2.9 km
Vernal Pool Loop
 1
Sharon, MA
The finish area is complete with Greylock in the background.

#7

13.0 mi 20.9 km
Mount Greylock Trail Race
 1
Adams, MA
You can occasionally find Meetup groups that head to Nickerson State Park.

#8

5.6 mi 9.0 km
Nickerson State Park
 1
Brewster, MA

Trails in Massachusetts - 220

Trail Run Project is built by runners like you. Add Your Trails

7.5 mi 12.1 km
#1 Skyline Trail
Winchester, MA
7.5 mi 12.1 km Winchester, MA
Unknown
Update
16 
1.1 mi 1.7 km
#2 Skyline Trail South
Milton, MA
1.1 mi 1.7 km Milton, MA
Unknown
Update
2 
0.3 mi 0.5 km
#3 Fern Trail
Northampton, MA
0.3 mi 0.5 km Northampton, MA
Unknown
Update
2 
22.8 mi 36.7 km
#4 Farmington Canal Heritage Trail: Northern Connecticut Section
North Granby, CT
22.8 mi 36.7 km North Granby, CT
Unknown
Update
1 
0.4 mi 0.7 km
#5 Awesome-Sauce Trail
Saugus, MA
0.4 mi 0.7 km Saugus, MA
Unknown
Update
1 
1.1 mi 1.8 km
#6 Morses Pond Trail
Wellesley, MA
1.1 mi 1.8 km Wellesley, MA
Unknown
Update
1 
89.1 mi 143.4 km
#7 AT: AMC - Berkshire Chapter (MA)
Canaan, CT
89.1 mi 143.4 km Canaan, CT
Minor Issues
Update
Snowy
77 days ago
1.1 mi 1.8 km
#8 Atlantic White Cedar Trail
North Eastham, MA
1.1 mi 1.8 km North Eastham, MA
Unknown
Update
1 
2.7 mi 4.3 km
#9 Moraine Trail - Northern Section
West Falmouth, MA
2.7 mi 4.3 km West Falmouth, MA
Unknown
Update
1 
1.2 mi 1.9 km
#10 Wild Side
Northampton, MA
1.2 mi 1.9 km Northampton, MA
Unknown
Update
1 
2.3 mi 3.7 km
#11 Harvey Mountain Trail
Austerlitz, NY
2.3 mi 3.7 km Austerlitz, NY
Unknown
Update
1 
0.7 mi 1.2 km
#12 Main Loop (Blue Trail)
Stow, MA
0.7 mi 1.2 km Stow, MA
Unknown
Update
1 
1.5 mi 2.4 km
#13 Pinnacle Trail
Austerlitz, NY
1.5 mi 2.4 km Austerlitz, NY
Unknown
Update
1 
1.8 mi 2.9 km
#14 Trilogy Trail
Ashby, MA
1.8 mi 2.9 km Ashby, MA
Unknown
Update
1 
0.4 mi 0.7 km
#15 Yellow Trail
Stow, MA
0.4 mi 0.7 km Stow, MA
Unknown
Update
1 
0.5 mi 0.8 km
#16 Knee Breaker
Northampton, MA
0.5 mi 0.8 km Northampton, MA
Unknown
Update
1 
0.8 mi 1.2 km
#17 Alter Ego
Austerlitz, NY
0.8 mi 1.2 km Austerlitz, NY
Unknown
Update
1 
0.3 mi 0.5 km
#18 No Man's Land
Northampton, MA
0.3 mi 0.5 km Northampton, MA
Unknown
Update
1 
2.6 mi 4.1 km
#19 Lake Waban
, Not set ()
2.6 mi 4.1 km , Not set ()
All Clear
Update
Dry, Mostly Dry
2 days ago
1 
7.9 mi 12.7 km
#20 Skyline Trail
Dedham, MA
7.9 mi 12.7 km Dedham, MA
Unknown
Update
4 

Photos of Massachusetts - 144

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While unnecessary, this water crossing certainly spiced up the run!

#1

While unnecessary, this water crossing certainl…
 3
Swansea, MA
Looking west from one of the many outlooks on this beautiful ridgeline.

#2

Looking west from one of the many outlooks on t…
 3
South Amherst, MA
Experiencing the Old King's Highway seems to bring you back in time.

#3

Experiencing the Old King's Highway seems to br…
 4
Truro, MA
Red-tailed hawk at Wachusett Meadow Wildlife Sanctuary.

#4

Red-tailed hawk at Wachusett Meadow Wildlife Sa…
 3
Princeton, MA
The view from the ridgeline.

#5

The view from the ridgeline.
 3
Hadley, MA
Heading back to the Try Island Trail boardwalk, looking east across the marsh toward the Nature Center.

#6

Heading back to the Try Island Trail boardwalk,…
 2
North Eastham, MA
Try Island Trail boardwalk.

#7

Try Island Trail boardwalk.
 2
North Eastham, MA
Average high tide marker for 2025 and the intersection of Goose Pond Trail and Try Island Trail.

#8

Average high tide marker for 2025 and the inter…
 2
North Eastham, MA

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