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Trail Running Calendar near New Canaan 2025-2026

Explore the top trail runs near New Canaan for 2025-2026! We've gathered 48 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km 13 mi 26 mi
Nov
27
Thursday

Milford Turkey Trot

2 mi 3 mi
Nov
27
Thursday

Bethel Turkey Trot

5 km
Nov
27
Thursday

The Joyce Allen Great Turkey Escape

5 km
Nov
27
Thursday

Westchester Turkey Trot 10K

5 km 10 km
Nov
27
Thursday

Shoreline Turkey Trot 5K

5 km
December 2025
Dec
13
Saturday

Frosty Forest 5K

Trail Run 5 km
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