Trail Runs in Massachusetts 2026 | Upcoming Races & Dates

Sun, Oct 11 · Milton, MA Milton

10k

From $20 Open Closing Soon

Sun, Oct 25 · Sudbury, MA Sudbury

10K Trail Race30K Trail race6-Hour Trail Race

From $40 Open 32 spots left

Sun, Oct 25 · Dover, MA Dover

1.5 Miler3.1 Miler5.6 Miler +1

From $20 Open

Sun, Oct 25 · Tyngsboro, MA Tyngsboro

Pumpkin Run 3K trail race

From $25 Open

Sun, Nov 1 · North Grafton, MA North Grafton

5K Farm RunHarvest Home Festival Tickets

From $10 Open Closing Soon

Sun, Nov 8 · Upton, MA Upton

10.5KHalf Marathon

From $30 Open

Sun, Nov 15 · Framingham, MA Framingham

5.3 Mile Trail Race10 Mile Trail Race

From $25 Open Closing Soon

Sun, Nov 15 · Sturbridge, MA Sturbridge

Ox Trot 2 Mile Walk5K RunKids Trot

From $15 Open

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