Trail Running calendar near Williams Bay 2026-2027

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.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Trail races of about 3 and 5 miles through the woods at Camp Big Timber in Elgin on November 8, 2026. The course runs on grass, gravel and single track and includes a creek crossing, participant shirts and a pancake breakfast.

Fast Track Cross Country Open in Schaumburg on November 8, 2026 features separate men's and women's 3 mile races, an optional team competition, packet pickup at Xtra Mile Running, a $25 registration fee, and spikes are recommended.

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.

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.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

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 2.5 mile chip timed cross country Turkey Trot on Thanksgiving morning in Orland Park, with long sleeve race shirts, a post race raffle, and prize turkeys for top finishers.

Regional cross country championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.

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.

A four-race winter trail series in Dixon, Illinois, featuring events from 5K to 20K across mixed terrain. Individual race and full-series entry options are available, with series awards and completion apparel for multi-race finishers.

A dog-focused trail run at Lake Geneva Ziplines and Adventures offering one or two loops on winding singletrack. Canicross and dog friendly options are available, with podium awards reserved for dog-equipped finishers and a finisher gift fo..

Quiet Silence on December 18, 2026 in Lake Mills, WI offers night out and back runs of 31 and 16 miles on a flat crushed limestone trail. The event includes aid stations, drop bags at the midway point, and required lights and reflective gea..

A winter trail series at Dick Young Forest Preserve in Batavia featuring 5K, 8K, and 10K races on separate dates in early 2027, with combined registration and a series swag reward program.

A winter obstacle race at Lake Geneva Ziplines & Adventures on January 30, 2027 offering distances from a kids loop to a 20K Yeti Challenge; fun heats allow optional obstacles while a competitive division awards cash prizes. All in-person f..