Grayslake
Trail Running Calendar near Grayslake 2026-2027
Explore the top trail runs near Grayslake 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.
September 2026
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.
An ultrarunning event at Richard Bong State Recreation Area offering 24h, 12h, 6h, and 3h formats, including a backyard 12-hour loop race and inclusion-focused entry options.
October 2026
Trail races in Lake County, Illinois offering 50 Mile, 50K, Marathon and Half Marathon on a flat crushed gravel course with timed cutoffs and multiple aid stations.
A family friendly fundraiser at Petrifying Springs Park offering 1 mile and 2.25 mile options to support Rey de Reyes Ministry in Guatemala with virtual participation available.
Experience a single track trail adventure through Veteran Acres and Sternes Woods in Crystal Lake featuring 5 and 10 mile distances and custom skeleton medals.
A fall race at Richardson Adventure Farm in Spring Grove featuring 10K, two 5K options and a 1 mile family run through the corn maze with finisher medals for all.
A 5K trail event in Pingree Grove featuring haunted sets, animatronics, multiple heats, a costume contest, bonfire, live entertainment, food, and free parking.
November 2026
A trail event at Pringle Nature Center on November 7, 2026 offering a 5K run and 2 mile walk with fees supporting environmental education.
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.
On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.
Thanksgiving morning 5K on the Green Bay Trail in Winnetka with rolling starts, three waves including a family division, packet pickup and postrace refreshments.
A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.
December 2026
Experience a technical trail race in Lake Geneva featuring 4 and 8 mile distances designed for both solo runners and Canicross enthusiasts with their dogs.
January 2027
Winter trail races in Crystal Lake IL with a 10K loop repeated for a 50K, plus 2 and 5 person relay options and on-course aid at Veteran Acres.