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Fall trail races near Chicago (2026)
Updated
8 trail races are on the calendar near Chicago in fall 2026, starting with Outlast Chicago on Saturday, October 24 in Palatine. That covers September to November. 6 of them publish an upcoming price increase, so signing up early saves money.
All fall races5K races (73)10K races (16)Half marathons (12)Trail races (8)
By date
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from $100Goes up Oct 22
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Run for Your Life Race at Robinson Lake - 5K and Haunted Fun Walk/Run
Sat Oct 24 · 6:00 PM · Hobart · Northwest Indiana
1 mile5KTrail
from $25 -
from $25Goes up Oct 20
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The Forge Trail Run Festival
Sat Nov 14 · 7:15 AM · Lemont · South Suburbs
10KHalf marathon18.6 miles37.2 milesTrail
from $62.50Goes up Oct 25 -
The Universal Sole November Trail Challenge
Sat Nov 21 · 10:00 AM · Willow Springs · South Suburbs
4 miles8 milesTrail
from $50Goes up Nov 1 -
from $35Goes up Nov 12
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from $39.99Goes up Nov 7
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Cancelled Holiday Cross Country Race & Reunion
Sun Nov 29 · 10:00 AM · Evanston · North Shore & North Suburbs
3.62 milesTrail
Other seasons near Chicago
Quick answers
How many trail races are near Chicago in fall 2026?
8 trail races are listed near Chicago in fall 2026. The first is Outlast Chicago on Saturday, October 24 in Palatine, and the last is Cancelled Holiday Cross Country Race & Reunion on November 29.
What is the cheapest trail race near Chicago in fall 2026?
Run for Your Life Race at Robinson Lake - 5K and Haunted Fun Walk/Run on October 24 has the lowest listed entry fee: $25. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Chicago?
Fast Track Cross Country Open: the 5K goes from $25 to $29 after October 20. 5 more of these trail races publish a later price increase.
Are there half marathons or marathons near Chicago in fall 2026?
Yes: 1 half marathon and 0 marathons. The first is The Forge Trail Run Festival on November 14.