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Running Calendar near Pawling 2026-2027

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Explore the top running races near Pawling for 2026-2027! We've gathered 112 exciting races in the area. Check out our detailed list below to find your next local race.

Running Calendar United States
Half Marathons Marathons Trail Runs Triathlons
August 2026
Aug
29
Sa

Roxbury Road Race Series

5 mi
Aug
29
Sa

Sgt. Scoular's Overdose Awareness and Recovery 5K

5 km
Aug
30
Su

Newtown Community Running Event

5 km 10 km Half Marathon
September 2026
Sep
5
Sa

Roxbury Road Race Series

Sep
5
Sa

Black Hog Brewing Co. 5K Road Race

5 km
Monthly updates for Pawling

Get new running races (and updates) in your inbox every month.
Sep
5
Sa

Sao Paio 5k

5 km
Sep
12-19
Sa

Paws Crossed 5K

5 km
Sep
12
Sa

Run 4 Hunger and Health

5 km
Sep
12
Sa

Buchanan Day 5K

5 km
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep
13
Su

High Watch Recovery Center's Sprint for Sobriety 5K

5 km
Sep
19-20
Sa - Su

Pawling 24 Hour Trail Running Festival

Backyard Ultra
Sep
19
Sa

Roxbury Road Race Series

4 mi
Sep
19-20
Sa - Su

Dutchess County Classic

5 km 10 km 13 mi
Sep
19
Sa

Katonah Road Race

5 km
Sep
19
Sa

West Point Remembrance Run

5 km
Sep
19
Sa

TYathlon Sprint Triathlon & 5K

Triathlon Sprint 0.25 10.5 2.7 mi
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
Sep
20
Su

Come Out & Run 5K

5 km
Sep
20
Su

MKFD Fired Up 5K

5 km
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