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.
Timed trail races at Richard Bong State Recreation Area offering 24 hour, multiple 12 hour formats, 6 hour and 3 hour options on September 26, 2026.
October 2026
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.
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.
Trail races in Crystal Lake on October 17, 2026 offering 10 mile and 5 mile courses through Veteran Acres and Sternes Woods.
A fall event at Richardson Adventure Farm in Spring Grove, IL with a 10K, a 5K through a corn maze, and a 1 mile family adventure, plus finisher medals for all.
A nighttime trail event in Pingree Grove, Illinois featuring multiple 5K heats through haunted sets with animatronics and actors, plus a costume contest, bonfire, live entertainment and food.
November 2026
A 5K trail run and 2 mile walk at Bristol Woods County Park supporting Pringle Nature Center environmental education, with youth pricing and event shirts.
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.
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.
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
A canicross-focused trail event in Lake Geneva, WI offering a 4-mile loop or two laps for 8 miles, with on-course aid and dog-only podium awards.