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Trail Running Calendar near Highland Park 2026-2027

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Explore the top trail runs near Highland Park for 2026-2027! We've gathered 20 exciting races in the area. Check out our detailed list below to find your next local race.

Trail Running Calendar United States
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
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
Sep
26
Sa

Bloomingdale Trail 5K

Trail Run 5 km
Monthly updates for Highland Park

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 Half Marathon Marathon 50 km 50 mi
Oct
18
Su

Richardson Farm Fall 10K with Family Adventure Run

Trail Run 5 km 10 km
Oct
24
Sa

Howl-o-ween 5k - Schaumburg

Trail Run 5 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
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
April 2027
Apr
17
Sa

Earth Day 50k

Trail Run 5 mi 15 mi 50 km
Apr
24
Sa

Childish Nonsense

Trail Run 6 mi 25 km 50 km 50 mi
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