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Trail Running Calendar near Highland Park 2025-2026

Explore the top trail runs near Highland Park for 2025-2026! We've gathered 119 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
1
Thursday

Cheers to New Year's 5k

5 km
Jan
10
Saturday

Frozen Gnome

Trail Run 10 km 50 km
Jan
31
Saturday

F3 Lake Half Marathon

5 km 13 mi
March 2026
Mar
15
Sunday

Lucky 7K

7 km
Mar
15
Sunday

Deer Park St. Paddy's 10K Run/Walk

5 km 10 km
April 2026
Apr
4
Saturday

Chi Town Half Marathon

10 km 13 mi
Apr
18
Saturday

Earth Day 50k

Trail Run 5 mi 15 mi 50 km
Apr
25
Saturday

Childish Nonsense

Trail Run 10 km 25 km 50 km 50 mi
Apr
26
Sunday

Ravenswood Run

5 km
May 2026
May
2
Saturday

Fight Hunger 10K

5 km 10 km
May
3
Sunday

Chicagoland Spring Marathon

10 km 13 mi 26 mi
May
9
Saturday

Pink 5k

5 km
May
10
Sunday

Barrington Mother's Day 5K

5 km
May
17
Sunday

Chicago Spring Half Marathon

10 km 13 mi
May
31
Sunday

North Shore Classic

5 km 13 mi
June 2026
Jun
21
Sunday

Fox Lake Sprint Triathlon

Triathlon
Jun
28
Sunday

Firecracker 5k - Kenosha

5 km
Jun
28
Sunday

Pleasant Prairie Triathlon

Triathlon
July 2026
Jul
11
Saturday

Savage Race - Chicago

Obstacle Run 3 mi 7 mi
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