Winnetka
Trail Running Calendar near Winnetka 2026-2027
Explore the top trail runs near Winnetka for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
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.
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 12 hour and 6 hour races on a 2 mile lakeside loop in Evanston with aid stations, public fountains, and handcrafted finisher awards.
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.
Trail races at Deer Grove Forest Preserve on Oct 24, 2026 offering 50K, 25K and 5-mile options on a runnable 5.5 mile loop with stocked aid stations and cash prizes.
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.
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 4.5 mile trail race at Schiller Woods West with crushed limestone and single/double track, on-site packet pick-up, finish-line chili and post-race raffle.
April 2027
May 2027
Trail marathon and 10 mile on Sag Valley Trail through Cap Sauers Nature Preserve with wide horse trail, multiple aid stations, and notable elevation.
Looped trail endurance event in Wolf Road Woods offering 7 or 11 hours on a four mile singletrack with an aid station stocked with hot dogs and pixie sticks.