Trail Running calendar near Williams Bay 2026-2027

USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve in Wheaton, IL, with finisher medals, chip timing, pacers and a virtual option.

An inaugural trail race in Verona, Wisconsin on September 5, 2026, offering 5K and 10K courses through prairies, woodlands, oak savannas and pine woods. Net proceeds support Prairie Moraine Friends and participant numbers are limited.

Last Dot Standing runs alternating one hour 4.2 mile legs between Belleville Community Park and Dot's Tavern in Belleville WI. Parallel 24 hour, 48 hour and 8 hour events use the same course and offer mile buckles and cash prizes.

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.

Echo 136 is a 136 mile trail race in Whitewater WI on the Ice Age State Trail with a 55 hour cutoff, nine stocked aid stations, and roughly 11,148 feet of elevation gain. Registration closes Sep 22 at 10:00 PM CT.

A grassroots loop ultra at Dixon Park District offering 25K, 50K, 100K and 100 mile options on a 7.85 mile mixed surface loop with two aid locations, crew and pacer policies, and finisher awards.

The Bloomingdale Trail 5K is an annual family-friendly running event in Chicago. It features a timed 5K race alongside shorter dashes for young runners. Registration is available for all three distances.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Experience a chip timed 5k trail run through the diverse terrain and scenic landscapes of Oakdale Nature Preserve. All proceeds support local park projects and trail maintenance.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

A community 5k run and walk hosted by the Lockport Fire Foundation on October 4, 2026 at Hassert Park in Lockport, IL. Entry includes a t-shirt and finisher medal for registered participants present on race day.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

A flat, fast trail event in Lake County on crushed gravel with 50 Mile, 50K, Marathon and Half Marathon options. The Marathon is Boston qualifying, the race is cup-less, and all finishers receive medals plus post-race food and awards.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Trail races of about 5 and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with single-track trails, a cupless course, packet pickup options, and finisher medals for all distances.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

A woodland ultra with 50K, 25K and 5-mile options run on a 5.5-mile single-track loop at Deer Grove Forest Preserve, featuring multiple stocked aid stations and explicit inclusion policies for race entries.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

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.