Trail Runs in Massachusetts 2026 | Upcoming Races & Dates

There are 8 trail runs in Massachusetts scheduled for 2026. The next is the Wildcat 5K Trail Run-Walk-Wag in Boxford on May 30. Massachusetts trail runs run primarily May through November.

Wildcat 5K Trail Run-Walk-Wag

Sat, May 30 · Boxford, MA Boxford

Wildcat Trail Run Walk Wag

From $30 Open Closing Soon

Stone Tower Half Marathon

Sun, Jun 21 · Lynn, MA Lynn

Stone Tower Half Marathon

From $80 Open

TVFR Woodland Trail Series

Thu, Jun 25 · Uxbridge, MA Uxbridge

TVFR Woodland Trail Series - JuneTVFR Woodland Trail Series - July & AugustTVFR Woodland Trail Series - June & August +4

From $10 Open

Greenbelt's Vineyard Hill Trail Run

Sat, Aug 22 · South Hamilton, MA South Hamilton

5k Trail Run - Non-members5k Trail Run - Members10k Trail Run - Members +1

From $35 Closed

Race for the Refuge

Sun, Sep 27 · Sudbury, MA Sudbury

10K Trail Race30K Trail race6-Hour Trail Race

From $40 Open 35 spots left

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 Closing Soon

Upton 10.5K and Half Marathon Trail Race

Sun, Nov 8 · Upton, MA Upton

10.5KHalf Marathon

From $30 Closed

Trail Runs in Massachusetts — 2026

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