COVID-19: At REI, we encourage you to get outside responsibly. Stay local, avoid recreational travel, practice social distancing and check ahead for area and facility closures. Learn More
Trail Run Project Logo

Boston Metro

Area suggestions or local tips? Tell us!

Zoom in to see details
Map Key

Weather Averages


High
 
Low
 
Precip
 
Days w/
 
J F M A M J J A S O N D

186 mi 299 km of trail 15 Runs

Easy Trails 110 Trails Intermediate Trails 66 Trails Hard Trails 10 Trails
Area suggestions or local tips? Tell us!
Trail Run Project is built by runners like you.
Share what you know about this area with the community.

Runs in Boston Metro - 15

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

Favorite short-coated brown dog
Intermediate

Skyline Trail

7.5 mi 12.1 km • Loop • 846 ft Ascent 257.71 m Ascent

(28) Winchester, MA
Favorite View from the Great Blue Hill
Difficult

Blue Hills Loop

4.1 mi 6.5 km • Loop • 1,171 ft Ascent 356.87 m Ascent

(16) Dedham, MA
Favorite A beautiful look at the fall leaves that are just beginning to turn color.
Intermediate

Ponkapoag Pond Loop

4.4 mi 7.0 km • Loop • 229 ft Ascent 69.67 m Ascent

(2) Milton, MA
Favorite An autumn view of Boston from the Fells
Intermediate

Wright's Tower Out-and-Back

0.9 mi 1.5 km • Out and Back • 138 ft Ascent 42 m Ascent

(1) Medford, MA
Favorite 20140406-DSC_0009
Difficult

Buck Hill Loop

5.3 mi 8.6 km • Loop • 583 ft Ascent 177.75 m Ascent

(2) Milton, MA
Favorite Middlesex Fells Reservation
Difficult

Rock Circuit Loop

4.6 mi 7.4 km • Loop • 619 ft Ascent 188.64 m Ascent

(5) Medford, MA
Favorite Large maple at Habitat Education Center and Wildlife Sanctuary.
Easy

Highland Farm Loop

1.4 mi 2.3 km • Out and Back • 39 ft Ascent 12 m Ascent

(2) Belmont, MA
Favorite Stone Bridge Waterfall" by Eric Kilby (https://www.flickr.com/photos/ekilby/9113874150/in/photolist-eTmZgd-eTmYqL-eTmZU1-eTazyP/), Flickr licensed under CC BY-SA 2.0 (https://creativecommons.org/licenses/by-sa/2.0/).
Easy

Virginia Woods Loop

0.9 mi 1.5 km • Out and Back • 117 ft Ascent 35.64 m Ascent

(2) Melrose, MA

Trails in Boston Metro - 171

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

2.2 mi 3.6 km #1Peabody Loop
Intermediate
Dover, MA
Intermediate
2.2 mi 3.6 km Dover, MA
0.5 mi 0.8 km #2Needham Reservoir Trail
Easy
Needham, MA
Easy
0.5 mi 0.8 km Needham, MA
1.5 mi 2.5 km #3Healthy Heart Trail
Easy
Melrose, MA
Easy
1.5 mi 2.5 km Melrose, MA
1.7 mi 2.8 km #4Page & Sadie Trail
Intermediate
Westwood, MA
Intermediate
1.7 mi 2.8 km Westwood, MA
0.8 mi 1.3 km #5Rock Hill Extension
Intermediate
Westwood, MA
Intermediate
0.8 mi 1.3 km Westwood, MA
1.8 mi 2.9 km #6Acton Path
Intermediate
Canton, MA
Intermediate
1.8 mi 2.9 km Canton, MA
1.1 mi 1.8 km #7Loop Trail
Easy
Canton, MA
Easy
1.1 mi 1.8 km Canton, MA
7.9 mi 12.7 km #8Skyline Trail
Difficult
Dedham, MA
Difficult
7.9 mi 12.7 km Dedham, MA
1.1 mi 1.7 km #9Skyline Trail South
Difficult
Milton, MA
Difficult
1.1 mi 1.7 km Milton, MA
2.2 mi 3.6 km #10Storrow Pond Trail
Intermediate
Westwood, MA
Intermediate
2.2 mi 3.6 km Westwood, MA
5.9 mi 9.5 km #11Reservoir Trail
Intermediate
Winchester, MA
Intermediate
5.9 mi 9.5 km Winchester, MA
5.8 mi 9.3 km #12Western Greenway
Intermediate
Belmont, MA
Intermediate
5.8 mi 9.3 km Belmont, MA
4.5 mi 7.2 km #13Landlocked Forest Loop (Yellow)
Intermediate
Lexington, MA
Intermediate
4.5 mi 7.2 km Lexington, MA
1.4 mi 2.2 km #14Webster Conservation Loop
Intermediate
Newton, MA
Intermediate
1.4 mi 2.2 km Newton, MA
1.1 mi 1.7 km #15Coon Hollow Path
Difficult
Milton, MA
Difficult
1.1 mi 1.7 km Milton, MA
2.4 mi 3.8 km #16Strawberry Hill Trail
Intermediate
Westwood, MA
Intermediate
2.4 mi 3.8 km Westwood, MA
1.0 mi 1.6 km #17Jejunum
Difficult
Burlington, MA
Difficult
1.0 mi 1.6 km Burlington, MA
1.0 mi 1.6 km #18Split Rock Trail
Intermediate
Westwood, MA
Intermediate
1.0 mi 1.6 km Westwood, MA
0.7 mi 1.1 km #19Strawberry Hill Alternate Trail
Difficult
Dover, MA
Difficult
0.7 mi 1.1 km Dover, MA
0.7 mi 1.2 km #20Zigzag Lollipop
Intermediate
Dover, MA
Intermediate
0.7 mi 1.2 km Dover, MA

Photos of Boston Metro - 124

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

Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
body of water near forest island
Feb 19, 2020 near Winchester, MA
short-coated brown dog
Feb 19, 2020 near Stoneham, MA
sunlight passing thru trees
Feb 19, 2020 near Winchester, MA
An autumn view of Boston from the Fells
Feb 19, 2020 near Medford, MA
snowy wood
Feb 19, 2020 near Winchester, MA
Middlesex Fells Reservation
Feb 19, 2020 near Medford, MA

Shop REI Adventures

Find More REI Adventures


Trail Run Project is part of the REI Co-op family,
where a life outdoors is a life well lived.

Shop REI Running