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Trail Running Calendar near Grayslake 2026-2027

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Explore the top trail runs near Grayslake 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
23
Su

Summer Trail Classic

Trail Run 4 mi 10 mi 13 mi
Aug
29
Sa

The Next Loop - Half Day Forest Preserve

Trail Run 5 km 10 km ... Marathon 50 km
Aug
30
Su

Cross Country Challenge 6k - Evanston

Trail Run 2 mi 6 km
September 2026
Sep
11
Fr

Woodland ROAR Run

Road Race Trail Run 5 km
Sep
26
Sa

Moraine Hills Run for the Hills

Trail Run 5 km 10 km 13 mi
Monthly updates for Grayslake

Get new running races (and updates) in your inbox every month.
October 2026
Oct
4
Su

Carrera de los Lancers 5K

Road Race Trail Run 5 km
Oct
10
Sa

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
17
Sa

Soul Crusher

Trail Run 5 mi 10 mi
Oct
18
Su

Richardson Farm Fall 10K with Family Adventure Run

Trail Run 5 km 10 km
Oct
23
Fr

Haunted Highlander Assault Trail Run

Trail Run 5 km
Oct
24
Sa

Howl-o-ween 5k - Schaumburg

Trail Run 5 km
November 2026
Nov
8
Su

Big Timber XC Challenge

Trail Run 3 mi 5 mi
Nov
8
Su

Fast Track Cross Country

Trail Run 3 mi
Nov
14
Sa

Abominable Trail Race

Trail Run 5 km 10 km 15 km 30 km
Nov
14
Sa

Nikki Cozzi-Carso Scholarship 5K

Road Race Trail Run 5 km
Nov
14
Sa

Feral Nonsense

Trail Run 3 mi 6 mi 9 mi
Nov
26
Th

Winnetka Turkey Trot

Trail Run 5 km
Nov
28
Sa

Midwest XC Championships

Trail Run 3 km 5 km
Nov
29
Su

ERC John Hennelly Public Cross Country Races

Trail Run 4 mi
December 2026
Dec
13
Su

Cold Coding

Trail Run 4 mi 8 mi
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