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Trail Running Calendar near Uptown 2025-2026

Explore the top trail runs near Uptown for 2025-2026! We've gathered 135 exciting races in the area. Check out our detailed list below to find your next local race.

April 2026
Apr
4
Saturday

Chi Town Half Marathon

10 km 13 mi
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

F^3 Cap Sauers Trail Marathon

Trail Run
May
9
Saturday

Quarryman Challenge

5 km 10 mi
May
9
Saturday

Pink 5k

5 km
May
10
Sunday

Barrington Mother's Day 5K

5 km
May
16
Saturday

Chicago 11 Hour Endurance Run

Backyard Ultra 4 mi
May
17
Sunday

Chicago Spring Half Marathon

10 km 21 km
May
31
Sunday

North Shore Classic

5 km 21 km
June 2026
Jun
7
Sunday

Leon's Triathlon

Triathlon
Jun
27
Saturday

Run the Runway - Wheeling

5 km
July 2026
Jul
4
Saturday

Warrenville Park District Firecracker 5K

5 km
August 2026
Aug
1
Saturday

College of DuPage Alumni 5k

5 km
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