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Trail Running Calendar near Pawling 2025-2026

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

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
27
Thursday

Roxbury Thanksgiving Day Charity Race

Trail Run 5 km
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
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
June 2026
Jun
4-7
Th - Su

Ironhike Endurance Series - Spring

Trail Run 15 mi 28 mi ... 100 mi 152 mi
October 2026
Oct
1-4
Th - Su

IronHike Endurance Series

Trail Run 152 mi
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