Trail Running calendar near Williams Bay 2026-2027

A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.

Trail races at New Glarus Woods State Park on August 15, 2026 include 16K, 8K, 5K and a free 1K kids run. Proceeds benefit Friends of New Glarus Woods State Park and awards include age-group prizes plus a 16K consistency award.

A community cross country style event at Lussier Stadium in Madison featuring a 5 km run and a 1 mile walk; established as a memorial and serving as a fundraiser for LaFollette High School middle school feeder schools.

Loop format trail event at Busse Woods in Ned Brown Forest Preserve on August 15, 2026. Runners complete 3.1 mile loops on crushed limestone and packed gravel with a centralized aid station and distances from 5K to 50K.

A continuous 40 or 50 mile loop race at Busse Woods on a 3.1 mile (5K) trail loop with fully stocked aid each lap and a 12 hour time limit. Personal supplies, crew zones, pacers, and on site medical staff support runners.

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.

A community road race in Elburn, IL on August 22, 2026 with 1-mile, 4-mile and 7-mile courses that cross the Union Pacific West rail line. The event benefits the Elburn Parks Commission and guarantees a racerback or tank if registered by Au..

A trail race at Paul Douglas Forest Preserve on August 23, 2026 offering approximate 4, 9.5 and 13 mile options. Part of the Dick Pond Athletics series with proceeds supporting the Chicago Area Mountain Bikers.

Tough Mudder Chicago at Richardson Adventure Farm on August 29 2026 offers 5K and 15K obstacle runs plus an 8 hour Infinity format, a Mudder Village with food and music, and finisher medals shirts and drinks.

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 ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.

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 5K and 10K trail run through 170 acres of restored prairie and oak savanna in Verona, Wisconsin. Proceeds support Prairie Moraine Friends and amenities include restrooms, aid stations, refreshments, and a takeaway gift.

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 community run and walk at Moraine Hills State Park offering 5K, 10K and half marathon options in person and virtually in September 2026, organized by volunteers to raise funds for park programs and improvements.