5K races in Massachusetts, United States — 2026 trail running calendar

Oct

03

Shrewsbury Trails 5K

Shrewsbury, Massachusetts, United States

$12.00 - $30.00

Trail running Walking Running

5K Kid Run

Oct

24

Sheriff's Meadow Foundation Fourth Trail Run

Edgartown, Massachusetts, United States

Free

Trail running

5K

Oct

25

Powisset Farm Trail Run - Fall

Dover, Massachusetts, United States

$20.00 - $49.00

Trail running

13.4K 9K 5K 2.4K

Oct

25

Ox Trot 5K

Sturbridge, Massachusetts, United States

$15.00 - $25.00

Trail running Walking Running

5K 3.2K Kids Trot

Oct

31

The Next Loop Endurance Series - New England

Wrentham, Massachusetts, United States

$90.00

Trail running

5K

Aug

22

Greenbelt's Vineyard Hill Trail Run

South Hamilton, Massachusetts, United States

Trail running

5K 10K

May

30

Wildcat 5K Trail Run-Walk-Wag

Boxford, Massachusetts, United States

Trail running

5K

May

26

Wayniacs Weekly Robinson Run

Agawam, Massachusetts, United States

Trail running

5K +10

May

25

Powisset Farm Trail Run - Spring

Dover, Massachusetts, United States

Trail running

13.8K 9K 5K 2.4K

May

16

15th Annual FBRTC 5K Trail Race and Walk

Franklin, Massachusetts, United States

Trail running

5K