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Trail Running Calendar near Wappingers Falls 2025-2026

Explore the top trail runs near Wappingers Falls for 2025-2026! We've gathered 16 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
19
Sunday

Run The Farm - Katonah

Trail Run 5 mi
Oct
19
Sunday

Castle to River Run - Garrison, NY

Trail Run 5 km Half Marathon
November 2025
Nov
1-2
Sa - Su

Fall Back Into The Trails Series

Trail Run 10 km 50 km 100 km
Nov
2
Sunday

8 Hours At The Farm

Trail Run 4 mi 4 hr 8 hr
Nov
8
Saturday

Beacon Bonfire 10k

Trail Run 10 km
Nov
9
Sunday

Raven Rocks 10k

Trail Run 10 km
Nov
9
Sunday

Taconic Road Runners FDR Park Cross County Run

Trail Run 6 km
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
30
Sunday

Rob's Trail Run

Trail Run 5 km
April 2026
Apr
4
Saturday

Big Bear Squatch North

Trail Run 10 km 13 mi
Apr
12
Sunday

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
25
Saturday

Squatchywaska Mountainfest

Trail Run 10 mi 25 km
Apr
26
Sunday

Jack Bristol Lake Waramaug Ultra Races

Trail Run 50 km 50 mi 100 km
Apr
26
Sunday

Leatherman's Loop

Trail Run 10 km
May 2026
May
3
Sunday

Breakneck Point Trail Runs

Trail Run Half Marathon Marathon
May
17
Sunday

Spring Run the Farm

Trail Run 5 mi
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