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Trail Running Calendar near Cheshire 2025-2026

Explore the top trail runs near Cheshire for 2025-2026! We've gathered 46 exciting races in the area. Check out our detailed list below to find your next local race.

March 2025
Mar
15
Saturday

Shamrock Run & Walk

2 mi 5 mi
Mar
15
Saturday

Catch A Leprechaun 5K

5 km
Mar
16
Sunday

O'Hartford 10K

5 km 10 km
Mar
16
Sunday

Run For The Shamrock

4 mi
Mar
22
Saturday

Daisy Dash - Westbrook

5 km
Mar
23
Sunday

Annual Johnny's Jog for Charity 5K

5 km
Mar
29
Saturday

Savin Rock Marathon

13 mi 26 mi
Mar
29
Saturday

Enchanted Forest Ultra Run

Backyard Ultra 50 km
Mar
29
Saturday

Fit for a Lifetime

5 km 10 km 13 mi
Mar
30
Sunday

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
Mar
30
Sunday

Steam Train Half Marathon

13 mi
Mar
30
Sunday

NVCC Food Pantry Run/Walk

5 km
April 2025
Apr
6
Sunday

Middletown 10K Run/Walk

5 km 10 km
Apr
13
Sunday

Cheshire Road Race

5 km 13 mi
Apr
19
Saturday

Traprock 50

Trail Run 17 km 50 km
Apr
26
Saturday

MahoneySabol 5K

5 km
Apr
26
Saturday

Deacon Chuck Dietsch Memorial 5K Run & Walk

5 km
Apr
26
Saturday

Naugatuck YMCA & Rotary 5K

5 km
Apr
27
Sunday

Run for Veterans

5 km 10 km
Apr
27
Sunday

Miles for Migraine Connecticut

2 mi 5 km
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