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Trail Running Calendar near Old Saybrook 2025-2026

Explore the top trail runs near Old Saybrook for 2025-2026! We've gathered 83 exciting races in the area. Check out our detailed list below to find your next local race.

August 2025
Aug
2
Saturday

John & Jessie Kelley Half Marathon

13 mi
Aug
3
Sunday

Race of Hope Southampton

5 km
Aug
7
Thursday

Cedar Lake Triathlon Series

Triathlon
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
19
Tuesday

Battle of Stonington 5K

5 km
Aug
23
Saturday

Saybrook Point 5k Road Race

5 km
Aug
24
Sunday

Sound to Bay 5K & 10K Run/Walk

5 km 10 km
September 2025
Sep
1
Monday

Faxon Law New Haven Road Race

5 km 20 km 13 mi
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
7
Sunday

Montville Race Day

5 km 10 km
Sep
13
Saturday

Wahaneeta Trail Run

Trail Run 5 km
Sep
13
Saturday

Run for the Hills - Niantic, CT

Trail Run 5 km
Sep
19
Friday

Charlie Stavros Memorial Beach Run

Trail Run 3 mi
Sep
20
Saturday

Bound for the Sound

5 km 10 km
Sep
20
Saturday

End the Stigma: Mental Health Awareness

5 km
Sep
21
Sunday

Cockaponsett Trails to a Cure

Trail Run 4 mi 9 mi
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