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Illinois Trail Running Calendar 2026-2027

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Monthly updates for Illinois

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

Explore the best trail runs in Illinois for 2026-2027! Our updated list features 61 exciting races across the region. Find your next race in Illinois below and join the running community at these great events!

August 2026
Aug
22
Sa

Comlara Trail Run

Trail Run 4 mi 13 mi 26 mi 51 mi
Aug
23
Su

Summer Trail Classic

Trail Run
September 2026
Sep
5
Sa

Temptation 200 Ultras

Trail Run 10 km 50 km 200 km
Sep
5
Sa

Gristmill Grind 10K

Trail Run 5 km 10 km
Sep
5
Sa

Naperville Trails Half Marathon

Trail Run 10 km Half Marathon
Sep
12
Sa

Wild Wild Wilderness

Trail Run 5 km 7 mi
Sep
12
Sa

Sand Creek Trail Run

Trail Run 4 mi 8 mi
Sep
26
Sa

Miles for Marshall 5K Trail Run

Trail Run 5 km
Sep
26
Sa

Hindsight Ultra Trail Runs

Trail Run 100 mi
October 2026
Oct
3-4
Sa - Su

The Hennepin Hundred

Trail Run 50 km 50 mi 100 mi
Oct
3
Sa

Run the Woods

Trail Run 5 km 8 km
Oct
10
Sa

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
16-17
Fr - Sa

Shake Your Trail Feather Trail Run

Trail Run 5 km 8 mi ... 50 km 100 km
Oct
17
Sa

Saw Wee Kee - Fall Trail Run

Trail Run
Oct
17
Sa

Jaimie Cox Memorial Run

Trail Run 2 mi 5 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
Oct
25
Su

Allerton Park Trail Run

Trail Run 2 mi 6 mi
November 2026
Nov
8
Su

Big Timber XC Challenge

Trail Run
Nov
14
Sa

The Forge Trail Run Festival

Trail Run 10 km 20 km 30 km 60 km