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Walking Events Calendar near Cheshire 2026-2027

Explore the top walking events near Cheshire for 2026-2027! We've gathered 68 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
Aug
15
Sa

Jill's Race for MS

Road Race Walk 3 mi
Aug
20
Th

Amber Room Run from the Sun

Road Race Walk
Aug
23
Su

Old Wethersfield 10K

Road Race Walk
Aug
29
Sa

Sgt. Scoular's Overdose Awareness and Recovery 5K

Road Race Walk
Aug
30
Su

Newtown Community Running Event

Road Race Walk 5 km
Monthly updates for Cheshire

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Aug
30
Su

Be Happy Road Race

Road Race Walk 3 mi
September 2026
Sep
12
Sa

Sterling Down and Dirty 5k

Obstacle Run Walk
Sep
12
Sa

Run 4 Hunger and Health

Road Race Walk 5 km
Sep
12
Sa

Riva Runs the Boardwalk 5K

Road Race Walk 5 km
Sep
13
Su

Farmington Memorial Walk

Walk 2 mi
Sep
13
Su

West Haven Community House Fun Walk

Walk 2 mi
Sep
19
Sa

Run to the River 5K

Road Race Walk 5 km
Sep
20
Su

Murray Lender Bagel Run 5K

Road Race Walk 2 mi
Sep
26
Sa

Pies & Pub Ta-Ta Trot 5K

Road Race Walk 5 km
Sep
26
Sa

Come on Over 5K

Road Race Walk 2 mi
Sep
26
Sa

The River Run - Simsbury, CT

Road Race Walk
Sep
26
Sa

Michelle's House Walk Run Bike

Road Race Walk
Sep
26
Sa

Chamber Challenge 5K

Road Race Walk
Sep
26
Sa

Community 5K

Road Race Walk 5 km
Sep
27
Su

Run/Walk To Save a Life 5K

Road Race Walk
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