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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 49 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
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
18
Saturday

The Best Races - Evanston

5 km 10 km 13 mi
Oct
26
Sunday

Haunted Halloween Half Marathon

5 km 13 mi
November 2025
Nov
23
Sunday

Lincolnwood Turkey Trot 10K

5 km 10 km
Nov
27
Thursday

Long Grove Turkey Trot 8K

5 km 8 km
Nov
27
Thursday

Grant Park Turkey Trot 10K

5 km 10 km
December 2025
Dec
6
Saturday

Arctic Frog Run - Libertyville, IL

Trail Run 5 km 10 km ... 25 km 50 km
Dec
6
Saturday

Santa Hustle Chicago

5 km 10 km
January 2026
Jan
31
Saturday

F3 Lake Half Marathon

5 km 13 mi
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