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Obstacle Race Calendar near Montauk 2025-2026

Explore the top obstacle runs near Montauk for 2025-2026! We've gathered 32 exciting races in the area. Check out our detailed list below to find your next local race.

June 2025
Jun
7
Saturday

Mighty Montauk Triathlon

Triathlon
Jun
14
Saturday

Beacon of Hope

5 km
Jun
15
Sunday

L+M Summer Stride 10k

5 km 10 km
Jun
21
Saturday

Shelter Island 10K & 5K Run/Walk

5 km 10 km
July 2025
Jul
6
Sunday

Southampton Firecracker 8K & 3M

3 mi 8 km
Jul
13
Sunday

Sailfest 5K

5 km
Jul
20
Sunday

Montauk Lighthouse Triathlon

Triathlon
August 2025
Aug
2
Saturday

John & Jessie Kelley Half Marathon

13 mi
Aug
3
Sunday

Race of Hope Southampton

5 km
Aug
6
Wednesday

Nick Bottone Mile

Aug
10
Sunday

Niantic Bay Triathlon

Triathlon
Aug
13
Wednesday

Stonington Cross Country 5K

Trail Run 2 mi 5 km
Aug
17
Sunday

Mohegan Striders 4-Miler

4 mi
Aug
17
Sunday

Ellen's Run

5 km
Aug
19
Tuesday

Battle of Stonington 5K

5 km
Aug
23
Saturday

Saybrook Point 5k Road Race

5 km
September 2025
Sep
6
Saturday

Groton City Brew Run

5 km
Sep
7
Sunday

Mighty Hamptons Steve Tarpinian Memorial Olympic Distance Triathlon

Triathlon
Sep
7
Sunday

Surftown Half Marathon

5 km
Sep
13
Saturday

Wahaneeta Trail Run

Trail Run 5 km
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