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Trail Running Calendar near Woodbury 2025-2026

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Explore the top trail runs near Woodbury for 2025-2026! We've gathered 15 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
27
Saturday

Front Runners New York Cross Country 5K

Trail Run 5 km
October 2025
Oct
5
Sunday

IBBC Trail Classic 5k

Trail Run 5 km
Oct
10
Friday

Tesla Hertz Run

Trail Run 10 mi 50 km ... 100 mi 150 mi
Oct
11
Saturday

Gemstone Sparkle Sprint 5k

Trail Run 5 km
Oct
12
Sunday

Paine to Pain Trail Half Marathon

Trail Run Half Marathon
Oct
12
Sunday

NSRF Great Pumpkin Dash Trail 5K

Trail Run 5 km
November 2025
Nov
8
Saturday

Pocantico Hills Marathon

Trail Run Half Marathon Marathon
Nov
8
Saturday

Veterans Day Cross Country Run

Trail Run 4 km
Nov
15
Saturday

NSRF Long Island Turkey Trail Trot 5K

Trail Run 5 km
Nov
29
Saturday

NSRF Leftover Turkey Trot 5K

Trail Run 5 km
Nov
30
Sunday

NSRF 50/50 Turkey Trot 5K

Trail Run 5 km
December 2025
Dec
7
Sunday

PPTC Endurance Fest

Trail Run 50 km 50 mi
Dec
13-14
Sa - Su

SRC Presents: a Backyard Ultra

Trail Run 4 mi
May 2026
May
2
Saturday

VCP 50K

Trail Run 50 km
July 2026
Jul
11
Saturday

Pinky’s Rock n Rolla

Trail Run 4 mi
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