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Trail Running Calendar near Cook County 2026-2027

Monthly updates for Cook County

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Cook County for 2026-2027! We've gathered 23 exciting races in the area. Check out our detailed list below to find your next local race.

August 2026
Aug
9
Su

Miles for Miracles Run

Trail Run 2 mi 3 mi
Aug
15
Sa

The Next Loop Endurance Series - Busse Woods

Trail Run 5 km 10 km ... 26 mi 50 km
Aug
15
Sa

40/50 Mile Challenge - Busse Woods

Trail Run 40 mi 50 mi
Aug
15
Sa

Bloom Alumni Cross Country Meet

Trail Run 2 mi
Aug
30
Su

Cross Country Challenge 6k - Evanston

Trail Run 4 mi
September 2026
Sep
5
Sa

Naperville Trails Half Marathon

Trail Run 10 km 13 mi
Sep
11
Fr

9/11 Stair Climb - Crown Point

Urban Trail Walk
Sep
12
Sa

Chicago Trail Running Festival

Trail Run Walk 5 km 10 km ... 30 km 50 km
Sep
26
Sa

Bloomingdale Trail 5K

Trail Run 5 km
Sep
26
Sa

Half Day at the Lake

Trail Run 2 mi
Sep
26
Sa

Hustle Up the Hill

Trail Run Walk 30 min
October 2026
Oct
4
Su

Fire Zone 5k

Trail Run 5 km
Oct
10
Sa

Gifts of Love Community 5K

Trail Run 3 mi
Oct
24
Sa

Fancy Nonsense 25K/50K

Trail Run 5 mi 25 km 50 km
Oct
24
Sa

Howl-o-ween 5k - Schaumburg

Trail Run 5 km
Oct
30
Fr

Witches in the Woods 5K

Trail Run Walk 5 km
November 2026
Nov
8
Su

Fast Track Cross Country

Trail Run 3 mi
Nov
14
Sa

The Forge Trail Run Festival

Trail Run 10 km 20 km 30 km 60 km
Nov
26
Th

Winnetka Turkey Trot

Trail Run 5 km
Nov
26
Th

Orland Park Turkey Trot

Trail Run 3 mi
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