Trail Running calendar near Jackson 2026-2027

Thanks Sandy in Sheboygan, WI is a 9 mile trail run at Kohler-Andrae State Park featuring beach shoreline, trails, a boardwalk and post-race snacks.

A community run/walk in Brillion honoring Mike Ariens, featuring 10K, 5K and a Kids 1K on trails and downtown routes, with finish-line ice cream, commemorative bucket hats, medals, and shuttle service between venues.

Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.

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.

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.

Participate in the annual Kettle Klomp featuring a 5k run and a 2 mile walk on a scenic cross country course. This community event supports the local high school cross country team and offers awards for various age groups.

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 mud obstacle event on August 29, 2026 at Richardson Adventure Farm offering 5K, 15K, timed Infinity laps, Mudder Village, and finisher rewards.

The 40/50 Mile Challenge - Half Day Forest Preserve will take place in Lincolnshire on Saturday 29 August 2026. You can run between 40 and 50 miles.

Loop based trail event at Half Day Forest Preserve where runners repeat a 3.1 mile loop, stop after any loop with no penalty, and receive official timing for each completed loop for combined results.

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 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 community run at Woodland Middle School in Gurnee on September 11, 2026, offering a 5K, 1 Mile, and a shirt only option. Proceeds support the Woodland PTA and confidential financial assistance for fees is available.

A USATF certified chip timed family 5K run and walk through Pla-Mor Park and the Devil's River State Recreational Trail in Francis Creek, WI. The event includes a virtual option and proceeds support local first responders and community prog..

A multi day event in Belleville WI with a Last Dot Standing format between Belleville Community Park and Dot's Tavern plus 24 and 48 hour races and long distance buckles.

Trail marathon and half marathon at High Cliff State Park on September 20, 2026, featuring technical singletrack, lake views, cupless support, and ages 16 and up.

Echo 136 is a 136 mile trail ultramarathon on the Ice Age State Trail in Whitewater WI with a 55 hour time limit and nine fully stocked aid stations.

In-person and virtual 5K, 10K and half marathon at Moraine Hills State Park with marked trails, water stations, and proceeds supporting park programs.

A 10th annual farm-based 5k trail run and family day in Fort Atkinson, WI supporting A-T research with in-person and virtual participation options.

Multi-hour trail running at Richard Bong State Recreation Area offering 24, 12, 6 and 3 hour options plus a backyard 24 loop format.