Trail Running calendar near Williams Bay 2026-2027

Multi-hour looped trail challenges at Blackhawk Ski Club in Middleton, WI, with individual and team relay options, plus a 1.7 mile fun run that highlights the course features and terrain.

Run the Rails in Elburn, Illinois on August 22, 2026 offers a 1 mile fun run plus 4 mile and 7 mile courses that begin and end at Prairie Park. Courses cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve on August 23, 2026. Part of the Dick Pond Athletics Darn Tough Trail Race Series with awards, raffle prizes, and proceeds benefiting Chicago Area Mountain Bike..

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm features 5K and 15K obstacle runs, an 8-hour Infinity lap format, Mudder Village festival amenities, and finisher medals, shirts, headbands and drinks.

A continuous loop trail race at Half Day Forest Preserve offering 3.1 mile laps for 40 or 50 mile distances, with a 12 hour cutoff and fully stocked aid at each lap. Crew access and personal staging areas are provided.

Loop based trail event at Half Day Forest Preserve near Vernon Hills, Illinois. Runners complete one 5K loop at a time on mostly flat crushed limestone, gravel and natural trails with centralized aid and crew access.

A technical trail event at Franklin Creek State Natural Area in Franklin Grove, IL, offering 5K and 10K courses with multiple creek crossings and about 100 ft elevation gain per mile. Runners, walkers, and ruckers take part and proceeds sup..

Timed 24 hour, 12 hour and 6 hour runs take place at Lapham Peak State Park on September 5 and 6, 2026, on a one mile loop with night lighting and chip timing. The event includes a cupless aid station and a Distance division.

A half marathon and 10k at Danada Forest Preserve in Wheaton on crushed limestone trails, finishing around the horse race track. USATF certified courses with chip timing, pacers, finisher medals, shuttle parking and packet mailing options.

A new trail race in Verona, Wisconsin offering 5K and 10K courses through prairies, woodlands and oak savannas. Net proceeds support Prairie Moraine Friends for park restoration; parking is limited and ride sharing is encouraged.

A three day trail event at Rock Cut State Park featuring a night 10 km plus 25 km and 50 km races, with single race entries and Triple Crown series options that award commemorative spike prizes to finishers.

A timed urban ultra at Horner Park with 3, 6 and 12 hour options on a short paved loop, hourly challenges, a single aid station, and two or four person relay teams.

An event in Belleville, WI that alternates hourly 4.2-mile legs between Belleville Community Park and Dot's Tavern until one runner remains; it also offers 24-hour, 48-hour, and 8-hour races with prize pots and mileage buckles.

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

A 136 mile point to point on the Ice Age State Trail through the Southern Kettle Moraine, with varied trail surfaces, nine staffed aid stations and full on-course support over an approximate 55 hour time limit.

A grassroots looped ultra in Dixon, IL, offering distances from about 8 miles to 100 miles on mixed singletrack, meadow, and gravel. Two aid stations, crew access, and pacers are allowed; medals and a buckle are awarded for finishers.

A multi-distance running and walking event at Moraine Hills State Park offering 5K, 10K and half marathon options in person and virtually during September 2026, with courses on crushed limestone trails and support stations along the routes.

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 hour and 12 hour events on a two mile loop along Evanston’s lakefront and the Northwestern University campus. The course has paved and crushed gravel sections, two aid stations, public fountains, and handcrafted finisher awards.

An annual trail run and family day in Fort Atkinson that raises funds for research into ataxia-telangiectasia. The event includes a 5k trail run, a one mile walk, kids races, and a virtual participation option.