Chicago
Trail Running Calendar near Chicago 2026-2027
Explore the top trail runs near Chicago for 2026-2027! We've gathered 27 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
Half marathon and 10K through Danada Forest Preserve on crushed limestone trails, USATF certified, chip timed with finisher medals and pacers for the half marathon.
A timed ultrarun in Chicago with 3 hour, 6 hour and 12 hour options on a roughly one mile loop, hourly playful challenges, on-course aid and relay team choices.
An obstacle course race at Indiana Dunes National Park on September 13, 2026, featuring 10k, 5K and a K9 3.1-mile event. The course uses varied landscapes to reflect terrains associated with military service.
Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.
Test your endurance at this 6 or 12 hour timed race featuring a scenic 2-mile loop along the Evanston lakefront and Northwestern University campus.
A 30 minute run or walk on Mt Hoy in Blackwell Forest Preserve that raises funds to house a family for two years through Bridge Communities.
A one-mile color run or walk at Montessori School of Lemont with a color-splashed t-shirt, eco-friendly confetti, and proceeds supporting outdoor learning.
October 2026
A 2 to 3 mile run or walk on October 3, 2026 in Midlothian Meadows with a guided visit to Bachelors Grove cemetery and a post-event beer and raffle.
The Lockport Fire Foundation presents the second annual Fire Zone 5k, a community 5k run and walk on a marked loop of the Forest Preserve trail starting at Hassert Park. Registered participants present on race day receive a t shirt and finisher medal..
A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.
Trail races on the flat, crushed gravel Des Plaines River Trail in Lake County Illinois offering half, marathon, 50K and 50 mile distances; the marathon is a Boston qualifier.
5K and 10K trail run and walk at Swallow Cliff South Forest Preserve in Palos Park, featuring gravel trails, sustainable race kits, and age group awards.
Trail races in Willow Springs on a 5.5 mile loop offering 50K, 25K and a 5 Miler with stocked aid stations, prize money, and inclusive entry options.
November 2026
A 3-mile cross-country race at the MacNider course in Schaumburg on November 8, 2026, with separate women's and men's races, optional team scoring, pre-race packet pickup, and a $25 registration fee.
Trail races at Wolf Road Woods with 8 mile two loop and 4 mile one loop options, post race chili and craft brews, plus age group and overall awards.
A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.