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Connecticut Walking Events Calendar 2026-2027

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Monthly updates for Connecticut

Get new walking events (and updates) in your inbox every month.

Explore the best walking events in Connecticut for 2026-2027! Our updated list features 100 great walks across the region. Find your next walk in Connecticut below and join the walking community at these great events!

August 2026
Aug
8
Sa

The Perogie Dash

Road Race Walk 5 km
Aug
8
Sa

Natchaug Stop the Stigma 5K Charity Run & Walk

Road Race Walk 5 km
Aug
8
Sa

Follow Natural Fitness Women's Health 5K

Road Race Walk
Aug
8
Sa

Woofbridge 5k Run

Road Race Walk 2 mi
Aug
9
Su

Run the Vineyards - Priam Vineyards 5K

Road Race Walk
Aug
9
Su

Torrington Road Race

Road Race Walk 3 mi
Aug
10-15
Mo - Sa

Step Up for the Brave

Urban Trail Walk 90 min
Aug
15
Sa

Jill's Race for MS

Road Race Walk 3 mi
Aug
18
Tu

Battle of Stonington 5K

Road Race Walk 5 km
Aug
20
Th

Amber Room Run from the Sun

Road Race Walk
Aug
23
Su

Unite to Fight 5K

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
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

Groton City Brew Run

Road Race Walk 5 km
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

Macedonia Trail Race

Trail Run Walk
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