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Trail Running Calendar near Wheeling 2026-2027

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Explore the top trail runs near Wheeling for 2026-2027! We've gathered 26 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026
Sep
12
Sa

Turbo Trot - Geneva

Trail Run 3 mi
Sep
26
Sa

Moraine Hills Run for the Hills

Trail Run 5 km 10 km 13 mi
Sep
26
Sa

Bloomingdale Trail 5K

Trail Run 5 km
Sep
26
Sa

Hustle Up the Hill

Trail Run 30 min
October 2026
Oct
4
Su

Carrera de los Lancers 5K

Road Race Trail Run 5 km
Monthly updates for Wheeling

Get new running races (and updates) in your inbox every month.
Oct
10
Sa

Des Plaines River Trail Races

Trail Run Half Marathon Marathon 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

Fancy Nonsense 25K/50K

Trail Run 5 mi 25 km 50 km
November 2026
Nov
7
Sa

Bristol Woods Trail Run

Trail Run 5 km
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

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
21
Sa

The Universal Sole November Trail Challenge

Trail Run 4 mi 8 mi
Nov
26
Th

Winnetka Turkey Trot

Trail Run 5 km
Nov
29
Su

ERC John Hennelly Public Cross Country Races

Trail Run 6 km
December 2026
Dec
12
Sa

The Universal Sole December Trail Challenge

Trail Run 5 mi
January 2027
Jan
9
Sa

Frozen Gnome

Trail Run 10 km 50 km
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