Winnetka
Trail Running Calendar near Winnetka 2026-2027
Explore the top trail runs near Winnetka for 2026-2027! We've gathered 24 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.
Trail races at Paul Douglas Preserve offering approximate 4, 9.5 and 13 mile single-track courses as part of the Dick Pond Athletics Darn Tough Trail Race Series.
September 2026
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.
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.
October 2026
Trail races on the flat, crushed gravel Des Plaines River Trail in Lake County offering Half Marathon, Marathon, 50K and 50 Mile distances.
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 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.