Trail Runs in Massachusetts 2026 | Upcoming Races & Dates

There are 7 trail runs in Massachusetts scheduled for 2026. The next is the Race for the Refuge in Sudbury on September 27. Massachusetts trail runs run primarily September through October.

Race for the Refuge

Sun, Sep 27 · Sudbury, MA Sudbury

10K Trail Race30K Trail race6-Hour Trail Race

From $40 Open 36 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 Closing Soon

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

The Next Loop Endurance Series - New England

Sun, Oct 31 · Wrentham, MA Wrentham

The Next Loop Endurance Series 5K, 10K, 1/2 Marathon, Marathon, 50KThe Next Loop Endurance Series 5K, 10K, 1/2 Marathon, Marathon, 50K

From $90 Closed

Trail Runs in Massachusetts — 2026