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Trail Running Calendar near Douglas 2026-2027

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Explore the top trail runs near Douglas for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.
Loop based endurance event at Busse Woods on August 15, 2026 offering repeated 3.1 mile laps over smooth crushed limestone and packed gravel. Distances range from 5K to 50K with a central aid station and open loop format.
Continuous 3.1 mile loop at Busse Woods near Elk Grove, IL offering 40 and 50 mile options with a fully stocked aid station every lap and a 12 hour cutoff. Runs alongside The Next Loop series but is scored separately.
Alumni cross country meet in Chicago Heights on August 15 2026 using the old 2 Miles course with decade-based teams, chip timing and place-based scoring.
A 6 km cross-country race at Lovelace Park in Evanston with scholastic races, team and individual entries, race shirts, awards, and a post-race gathering with food.
September 2026
USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve with chip timing, pacers, shuttle parking and finisher medals.
A timed urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.
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.
Timed 6 and 12 hour events on a 2 mile lakefront loop in Evanston with two aid stations, public water fountains, nearby parking, and a nonalcoholic finish beverage and finisher award.
A 30 minute run or walk up Mt. Hoy in Blackwell Forest Preserve, Warrenville IL, with proceeds funding two years of housing through Bridge Communities.
October 2026
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.
A trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.
Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.
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.
A trail festival in Lemont on November 14, 2026, offering 10K, 20K, 30K and 60K on single and double-track trails and gravel around the Lemont Quarries and I&M Canal, with multi-lap courses and variable terrain.
An annual canicross friendly 5K at Deer Grove-East in Palatine on November 14 2026 supporting a local scholarship fund, with awards, refreshments and a paved course option.
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.
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