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Trail Running Calendar near Windsor 2025-2026

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Explore the top trail runs near Windsor for 2025-2026! We've gathered 126 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
10
Saturday

Country to Capital Ultra Marathon

Trail Run 43 mi
February 2026
Feb
7-8
Sa - Su

Pilgrim Challenge

Trail Run 66 mi
March 2026
Mar
8
Sunday

Leith Hill Half Marathon

Trail Run 13 mi
Mar
14
Saturday

Humanity Direct Amersham Ultra

Trail Run 10 km 25 km 50 km
Mar
14
Saturday

Centurion Hundred Hills 50km

Trail Run 50 km
April 2026
Apr
18
Saturday

Windsor 50 Ultra Challenge

Trail Run 10 km 25 km 50 km
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