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Trail Running Calendar near Westchester 2025-2026

Explore the top trail runs near Westchester for 2025-2026! We've gathered 170 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
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
20
Saturday

1911 Initiative 5k Scholarship Run/Walk

5 km
Jun
27
Saturday

Miles for Maddog

5 km 10 km
July 2026
Jul
4
Saturday

Warrenville Park District Firecracker 5K

5 km
August 2026
Aug
8
Saturday

Raceway 5K

3 km 5 km
Aug
15
Saturday

MyBFF 8.13K

5 km 8 km
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