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© 2026 SportPlan. All rights reserved.

by Dockia Labs

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Trail Running in Chicago 2026 | SportPlan
Trail Running in Chicago
Trail RunningChicago

Trail Running in Chicago

Browse upcoming amateur trail running events and compare dates, locations, and popularity. in Chicago.

Upcoming dates Chicago Community-rated events
27 events found

27 eventos

Sort: recommended
DateEventSportLocationDist.27
4JUN
Chicago's Race Against Gun Violence
Trail Running5 kmChicago
Trail Running
Chicago
5 km
6JUN
Saw Wee Kee Summer Trail Run
Trail RunningOswego
Trail Running
Oswego
—
7JUN
Hickory Knolls Trail Run
Trail RunningKane County
Trail Running
Kane County
—
7JUN
The 5K Monarch March
Trail Running5 kmElk Grove Village
Trail Running
Elk Grove Village
5 km
13JUN
Lace Up 5K Run, Walk and Kids 100 Yard Dash
Trail Running5 kmHomer Glen
Trail Running
Homer Glen
5 km
20JUN
NFP - Shopping Cart Shuffle
Trail Running5 kmCarol Stream
Trail Running
Carol Stream
5 km
27JUN
Furry Friends 5K - Celebration Run
Trail Running5 kmMettawa
Trail Running
Mettawa
5 km
18JUL
Log 250 Miles for America's 250 with the Fabulous Fox! National Water Trail thru Kane County
Trail RunningKane County
Trail Running
Kane County
—
18JUL
Road Warrior Relay
Trail RunningCarol Stream
Trail Running
Carol Stream
—
1AUG
Oakadoke Trail Runs
Trail RunningPorter County
Trail Running
Porter County
—
8AUG
Back-to-School Family Fun 5K
Trail Running5 kmWheeling
Trail Running
Wheeling
5 km
23AUG
Summer Trail Classic
Trail RunningPaul Douglas Preserve
Trail Running
Paul Douglas Preserve
—
5SEP
Naperville Trails Half Marathon
Trail Running21.1 kmNaperville
Trail Running
Naperville
21.1 km
12SEP
Timely Nonsense
Trail RunningChicago
Trail Running
Chicago
—
26SEP
Bloomingdale Trail 5K
Trail Running5 kmChicago
Trail Running
Chicago
5 km
26SEP
Run for the Hills
Trail Running21.1 kmMcHenry County
Trail Running
McHenry County
21.1 km
26SEP
ZERO Prostate Cancer Run/Walk Chicago SEA Blue
Trail Running5 kmChicago
Trail Running
Chicago
5 km
27SEP
F3 Naperville Foundation 5K
Trail Running5 kmDuPage County
Trail Running
DuPage County
5 km
3OCT
Boo Island - 5K Charity Run/Walk
Trail Running5 kmBlue Island
Trail Running
Blue Island
5 km
3OCT
Hops for Hope 5K & BrewFest
Trail Running5 kmSt. Charles
Trail Running
St. Charles
5 km
3OCT
Long Grove's Prairie State Oktober Fest 5K
Trail Running5 kmLong Grove
Trail Running
Long Grove
5 km
3OCT
Tryon Farm 4 Miler/8 Miler/25k/50k and 2 mile Fun Run/Walk
Trail RunningLaPorte
Trail Running
LaPorte
—
17OCT
Chicago Fall Classic Half Marathon 10K & 5K
Trail Running21.1 kmChicago
Trail Running
Chicago
21.1 km
17OCT
Rosehill Cemetery Crypt 5K
Trail Running5 kmChicago
Trail Running
Chicago
5 km
18OCT
Run with the Nuns 5K
Trail Running5 kmLemont
Trail Running
Lemont
5 km
25OCT
Wheaton Hot Cider Hustle
Trail Running5 kmWheaton
Trail Running
Wheaton
5 km
1JAN
Resolution Run 6K
Trail Running6 kmOlympia Fields
Trail Running
Olympia Fields
6 km

Other sports in Chicago

Trail Running in other areas

Events listed

27

Sport

Trail Running

Area

Chicago

Radius

70 km

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Updated Jun 10, 2026