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Obstacle Race Calendar near Highland Park 2025-2026

Explore the top obstacle runs near Highland Park for 2025-2026! We've gathered 27 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
14
Sunday

El Grito Family Run/Walk

5 km
Sep
27
Saturday

Lawndale 5K

5 km
Sep
28
Sunday

Lester Fun Run

5 km
Sep
28
Sunday

Chicago Half Marathon

5 km 13 mi
October 2025
Oct
4
Saturday

Long Grove's Prairie State Half Marathon

5 km 10 km 13 mi
Oct
5
Sunday

Bronzeville 5K

5 km
Oct
5
Sunday

Chicago 5k

5 km
Oct
11
Saturday

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
12
Sunday

Chicago Marathon

Oct
18
Saturday

Spooky Sprint - Chicago

5 km 10 km 13 mi
Oct
18
Saturday

Rosehill Cemetery 'Crypt' 5K

5 km
Oct
18
Saturday

Country Sole Half Marathon

5 km 10 km 13 mi
Oct
26
Sunday

Haunted Halloween Half Marathon

5 km 13 mi
December 2025
Dec
6
Saturday

Arctic Frog Run - Libertyville, IL

Trail Run 5 km 10 km ... 25 km 50 km
January 2026
Jan
31
Saturday

F3 Lake Half Marathon

5 km 13 mi
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