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Walking Events Calendar near Sleepy Hollow 2026-2027

Explore the top walking events near Sleepy Hollow for 2026-2027! We've gathered 118 great walks in the area. Check out our detailed list below to find your next local walk.

September 2026
Sep
13
Su

Run for Tomorrow 5K - Elburn

Road Race 5 km
Sep
13
Su

Santa Maria del Popolo 5K Run/Walk

Road Race 5 km
Sep
19
Sa

Lions Heritage Fest 5K Run

Road Race
Sep
19
Sa

Gather 5K

Road Race 2 mi 5 km
Sep
19
Sa

Run for the Stars

Road Race 5 km
Monthly updates for Sleepy Hollow

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Sep
19
Sa

Step It Up Walk/Run

Road Race
Sep
19
Sa

Sunbeams Uganda 5K

Road Race
Sep
19
Sa

West Chicago Fit4Fall

Road Race 5 km
Sep
19
Sa

Sugar Grove's Run to Remember

Road Race
Sep
20
Su

Fun Run and Family Walk

Road Race
Sep
20
Su

Headless Horseman Hussle

Road Race
Sep
20
Su

Run to Read

Road Race
Sep
20
Su

Willow House Walk and 5K Run for Hope

Road Race
Sep
20
Su

D67 Dash

Road Race 5 km
Sep
20
Su

Race to Zero

Road Race 5 km
Sep
24
Th

Beignet 5K

Road Race 5 km
Sep
26
Sa

The Single & Mingle 5K at the VFW

Road Race
Sep
26
Sa

Moraine Hills Run for the Hills

Trail Run 5 km 10 km 13 mi
Sep
26
Sa

I'm Here for the Food (Pantry) 5K

Road Race 5 km
Sep
26
Sa

Friends of the Poor Walk and Run

Road Race 5 km
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