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

Half Marathons Marathons Trail Runs Triathlons
December 2026
Dec
19
Sa

New Canaan Santa Run

5 km
January 2027
Jan
1
Fr

Brookfield Lions Run for Sight

4 mi
February 2027
Feb
28
Su

Lake Waramaug Polar Bear Run

8 mi
March 2027
Mar
14
Su

Fallen Comrades Half Marathon

13 mi
April 2027
Apr
3
Sa

Big Bear Squatch North

Trail Run 10 km 13 mi
Monthly updates for Pawling

Get new running races (and updates) in your inbox every month.
Apr
4
Su

John Jay Community Trail Race

Trail Run 5 km
Apr
11
Su

Millbrook Marathon

26 mi
Apr
18
Su

Try the Trail

Trail Run
Apr
25
Su

Jack Bristol Lake Waramaug Ultra Races

50 km 50 mi 100 km
Apr
25
Su

Leatherman's Loop

Trail Run 10 km
May 2027
May
1
Sa

Rock The Ridge

Trail Run 26 mi 50 mi
May
2
Su

Hudson Valley Marathon

3 mi 6 mi 13 mi 26 mi
May
8
Sa

Breakneck Point Trail Runs

Trail Run Half Marathon 15 mi Marathon 27 mi
May
15
Sa

Millbrook Vineyards Wine Run 5k

Trail Run 5 km
May
16
Su

Rossiter Run

5 km
May
16
Su

BoFish Triathlon

Triathlon BoFish Triathlon 1 25 5 mi Relay Team 1 25 5 mi
May
21
Fr

Moonlight 5K - New Milford

5 km
May
22
Sa

Brooklyn Cider House Spiked Apple 5K

Trail Run 5 km
May
23
Su

Spring Run the Farm

Trail Run 5 mi
May
24
Mo

South Salem Memorial Day Races

5 km 10 km 15 km
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