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Obstacle Race Calendar near Gloucester 2025-2026

Explore the top obstacle runs near Gloucester for 2025-2026! We've gathered 27 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
27
Thursday

Hingham Turkey Trot

5 km
Nov
27
Thursday

T4G (Thanks for Giving) 5k/10k

December 2025
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
7-8
Su - Mo

Jingle Bell Half Marathon

5 km 13 mi
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
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