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Trail Running Calendar near Shelter Island Heights 2025-2026

Explore the top trail runs near Shelter Island Heights for 2025-2026! We've gathered 8 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
4
Saturday

CFA Trail 5K

Trail Run 5 km
Oct
5
Sunday

Run the Vineyards - Pindar Fall 8K

Trail Run 5 km 8 km
Oct
12
Sunday

Goodwin Trail Challenge

Trail Run 45 mi
Oct
19
Sunday

Bimblers Bluff 50k

Trail Run 50 km
Oct
26
Sunday

Race for the Greenway 5K

Trail Run 5 km
November 2025
Nov
2
Sunday

Stonington Vineyards Wine Run Turkey Trot 5k

Trail Run 5 km
Nov
16
Sunday

Brookhaven Trail Half Marathon

Trail Run 5 mi Half Marathon
March 2026
Mar
21
Saturday

Ospreys Dominion Wine Run 5K

Trail Run 5 km
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