Massachusetts Trail Running Calendar 2025-2026

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Explore the best trail runs in Massachusetts for 2025-2026! Our updated list features 181 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

November 2025
Nov
9
Sunday

Harborside Half Marathon

5 km 13 mi
Nov
9
Sunday

Boston River Run

5 km
Nov
16
Sunday

The Baystate Dirty Dog Trail Run

Trail Run 5 km
Nov
22
Saturday

Roadtown Turkey Trot

5 km
Nov
22
Saturday

Rachel's Run

5 km
Nov
27
Thursday

Running of the Pilgrims 5K

5 km
Nov
27
Thursday

Will Run for Pie - Turkey Trot 5K

5 km
Nov
27
Thursday

Hingham Turkey Trot

5 km
Nov
27
Thursday

Holden Turkey Trot

5 km
Nov
30
Sunday

Tough 10 Turkey Trot

5 mi 10 mi
December 2025
Dec
6
Saturday

Winter Lights 5K

5 km
Dec
6
Saturday

TARC Winter Classic

Trail Run 8 mi 32 mi 40 mi
Dec
7
Sunday

Happy Holidays Half Merrython

5 km 13 mi
Dec
7
Sunday

Winter Classic

5 km
Dec
7
Sunday

Woo Jingle 5K

5 km
Dec
7-8
Su - Mo

Jingle Bell Half Marathon

5 km 13 mi
Dec
7
Sunday

Medfield Foundation Angel Run

5 km
Dec
14
Sunday

Santa's Toy Trot 6-mile Road Race

2 mi 4 mi 6 mi
January 2026
Jan
1
Thursday

New Year's Day Hangover Classic

5 km 10 km
February 2026
Feb
7-8
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi 30 hr
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