Highland Park close

Trail Running Calendar near Highland Park 2025-2026

Explore the top trail runs near Highland Park for 2025-2026! We've gathered 94 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
13
Saturday

The Best Races - Chicago

5 km 10 km 13 mi
Dec
13
Saturday

The Best Races - Evanston

5 km 10 km 13 mi
Dec
27
Saturday

The Best Races - Chicago

5 km 10 km 13 mi
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
April 2026
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
9
Saturday

Pink 5k

5 km
May
17
Sunday

Chicago Spring Half Marathon

10 km 13 mi
May
31
Sunday

North Shore Classic

5 km 13 mi
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series