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Running Calendar near Cheshire 2025-2026

Monthly updates for Cheshire

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

Explore the top running races near Cheshire for 2025-2026! We've gathered 63 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
April 2026
Apr
12
Su

Cheshire Road Race

5 km Half Marathon
Apr
18
Sa

Race for Your Mental Health

5 km
Apr
18
Sa

Traprock 50

Trail Run 17 km 50 km
Apr
25
Sa

Shane Kinsella Memorial Run/Walk

2 mi 5 mi
Apr
25
Sa

Deacon Chuck Dietsch Memorial 5K Run & Walk

5 km
Apr
25
Sa

Gilbert Joseph & Brian 5K

3 mi
May 2026
May
3
Su

Edmund Ganem Memorial 5K Run/Walk

5 km
May
3
Su

The Blue 2 Blue Challenge

Trail Run 50 km
May
10
Su

WeCare-Mother's Day 5K

5 km
May
15
Fr

Moonlight 5K - New Milford

5 km
May
16
Sa

Forgotten Forest Ultra Run - Stratford, CT

Backyard Ultra 2 mi
May
16
Sa

Run Ragged Last One Standing

Backyard Ultra 3 mi
May
16
Sa

Reservoir Rush

5 km
May
17
Su

BoFish Triathlon

Triathlon
May
23
Sa

Hamden Hills Half Marathon & Flat 5K

5 km Half Marathon
May
24
Su

Mine Hill Half Marathon

Trail Run Half Marathon
May
25
Mo

Oh Boy 5K

5 km
June 2026
Jun
6
Sa

SongStrong

5 km
Jun
7
Su

Brookfield Lions Strides to Cure Diabetes 5-Miler

5 mi
Jun
13
Sa

Gaylord Gauntlet

Obstacle Run 5 km