Trail Runs in Massachusetts 2026 | Upcoming Races & Dates

There are 7 trail runs in Massachusetts scheduled for 2026. The next is the Greenbelt's Vineyard Hill Trail Run in South Hamilton on August 22. Massachusetts trail runs run primarily August through November.

Greenbelt's Vineyard Hill Trail Run

Sat, Aug 22 · South Hamilton, MA South Hamilton

5k Trail Run - Members5k Trail Run - Non-members10k Trail Run - Non-members +1

From $35 Open

Race for the Refuge

Sun, Sep 27 · Sudbury, MA Sudbury

10K Trail Race30K Trail race6-Hour Trail Race

From $40 Open 35 spots left

2026 Shrewsbury Trails 5K

Sat, Oct 3 · Shrewsbury, MA Shrewsbury

5K Trail RaceTrail WalkKid Run

From $12 Open

Houghton's Pond Trail Races (7 Miles and 3.7 Miles)

Sun, Oct 4 · Milton, MA Milton

3.7-Mile Race7-Mile Race

From $30 Open

Powisset Farm Trail Run - Fall

Sun, Oct 25 · Dover, MA Dover

1.5 Miler3.1 Miler5.6 Miler +1

From $20 Open

Upton 10.5K and Half Marathon Trail Race

Sun, Nov 8 · Upton, MA Upton

10.5KHalf Marathon

From $30 Open

2026 GFRC Busa Bushwhack Trail Races

Sun, Nov 15 · Framingham, MA Framingham

5.3 Mile Trail Race10 Mile Trail Race

From $25 Open

Trail Runs in Massachusetts — 2026