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5K Race Calendar near Sleepy Hollow 2026-2027

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Explore the top 5k races near Sleepy Hollow for 2026-2027! We've gathered 167 exciting races in the area. Check out our detailed list below to find your next local race.

June 2027
Jun
12
Sa

Waubonsee Foundation Trail Run

Trail Run 5 km 10 km
Jun
19
Sa

The Longest Day Run

Race Roster 5 km 10 km
The Longest Day Run
Jun
26
Sa

Run the Runway - Wheeling

5 km
July 2027
Jul
4
Su

Warrenville Park District Firecracker 5K

5 km
August 2027
Aug
7
Sa

Highlander Assault Obstacle Race

Obstacle Run 3 km 5 km 15 km 50 km
Monthly updates for Sleepy Hollow

Get new running races (and updates) in your inbox every month.
Aug
14
Sa

MyBFF 5K/8.13K

5 km 8 km
Aug
28-29
Sa - Su

Tough Mudder - Chicago

Obstacle Run 5 km 15 km
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