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

Half Marathons Marathons Trail Runs Triathlons
May 2027
May
2
Su

Hudson Valley Marathon

3 mi 6 mi 13 mi 26 mi
May
2
Su

Breakneck Point Trail Runs

Trail Run 15 mi 27 mi
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
Monthly updates for Pawling

Get new running races (and updates) in your inbox every month.
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
June 2027
Jun-Aug
1-31
Tu

Summer Sizzler 2-Miler

2 mi
Jun
6
Su

Fire Tower Trail Races

Trail Run 10 km 13 mi
Jun
12
Sa

Pawling Triathlon

Triathlon Pawling Triathlon 0.3 12 3.1 mi Relay 0.3 12 3.1 mi
Jun
13
Su

Litchfield Hills Road Race

7 mi
Jun
27
Su

Stissing Triathlon

Triathlon AquaBike 800 m 12.6 mi Sprint 800 m 12.6 3.3 mi RELAY TEAM 800 m 12.6 3.3 mi
July 2027
Jul
14
We

Bowdoin Bushwhack

Trail Run 5 mi
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