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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 42 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
22
Saturday

Sargent Elementary Turkey Trot 5K

Trail Run 5 km
Nov
23
Sunday

Run for the Turkeys 5K Road Race

5 km
Nov
23
Sunday

Head for the Hilltop 5K

Trail Run 5 km
Nov
23
Sunday

After the Leaves/Josh Feldt Half Marathon

Trail Run Half Marathon
Nov
27
Thursday

Family of New Paltz Turkey Trot

5 km
Nov
27
Thursday

Wallkill East Rotary Turkey Trot

5 km
Nov
27
Thursday

Thanksgiving Turkey Trot - Shenorock

Trail Run 5 km
Nov
27
Thursday

Rhinebeck Ferncliff Forest Turkey Trot

5 km
Nov
29
Saturday

Run Santa Run - New Milford

5 km
Nov
30
Sunday

Rob's Trail Run

Trail Run 5 km
Nov
30
Sunday

Orange Runners Club Jingle Jog 4 Mile Run/Walk

4 mi
December 2025
Dec
7
Sunday

Reindeer Ramble

5 km
Dec
13
Saturday

HV Hawks 5k Reindeer Dash

5 km
Dec
17
Wednesday

Fleet Feet Poughkeepsie's Red Suit Ramble

5 km
January 2026
Jan
1
Thursday

Brookfield Lions Run for Sight

4 mi
April 2026
Apr
4
Saturday

Big Bear Squatch North

Trail Run 10 km 13 mi
Apr
12
Sunday

Millbrook Marathon

26 mi
Apr
12
Sunday

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
18
Saturday

ADAC Run/Walk/Roll For Recovery 5k

5 km
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