Trail Running calendar near Jackson 2026-2027

Trail marathon and half marathon at High Cliff State Park near Sherwood WI on September 20, 2026, featuring Lake Winnebago views, technical single track and prairie sections. Aid stations, a postrace pasta buffet, and a cupless policy are p..

Echo 136 in Whitewater, WI is a 136 mile trail ultramarathon on the Ice Age State Trail with a 55 hour cutoff and 10 aid stations. The event lists about 11,148 ft of ascent and is organized by TYDISH Running.

A multi-distance run and walk at Moraine Hills State Park on September 26, 2026 offering 5K, 10K and half marathon options plus a virtual period in September to support Friends of Moraine Hills State Park.

Emmy's Rustic Run is a Fort Atkinson trail run and family fun day raising funds for the A-T Children's Project, featuring a 5k, a one mile walk, kids races and virtual participation.

Backyard Nonsense is a timed trail event at Richard Bong State Recreation Area in Brighton WI offering 3 hour, 6 hour, 12 hour and 24 hour formats. The 24 hour options include a backyard loop format and a continuous 24 hour option; a 2026 p..

Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

A fall trail event at Lapham Peak State Forest featuring timed 5K and 10K runs, accessible walk options, and a free 1K Smokey Bear run for children age 10 and under; participant shirts, awards, and post-event treats are included.

Two trail routes around Indian Lake County Park in Cross Plains, Wisconsin feature wetlands, forested slopes, and a section of the Ice Age Trail. The event is cup free and includes post-race music, food, and awards.

A community 2-mile cross country run/walk at Glacier Creek Middle School with in-person and virtual options, evening and race-day packet pickup, live electronic results, and awards; proceeds support course upkeep and the high school cross-c..

A community 5k and a 54 yard dash on October 4, 2026 in Glendale with an out-and-back course on the Oak Leaf Trail. Registration includes all-day entry to Milwaukee's Original Oktoberfest at Old Heidelberg Park.

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 loop-based trail ultra in Eagle, Wisconsin offering 6, 12 and 20 hour formats for solo runners or relay teams up to four people, set on three mapped autumn loops through the Southern Kettle Moraine Forest.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

Trail runs and a 1-mile walk at Fox Hill Nature Preserve on 10/11/2026, held to support conservation in the Cedar Lakes region; varied distances include 5K, 10K, a 1-mile walk, and a Kiddos 1K.

A fall ultramarathon on the Ice Age Trail near Greenbush, Wisconsin offering 50 mile and 50K out and back courses. Aid stations are spaced four to eight miles and the event is cupless with reusable cups provided at check in.

Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.

Trail races of about 5 miles and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with race shirts and finisher medals, a cup-less format, and a 3 hour 30 minute cutoff.

National Sweetest Day at Nashotah Park on October 17, 2026 offers running, walking, and ruck events from a kids 1K to a half marathon. Entry fees vary and several events include post race treats.

A fall event at Richardson Adventure Farm in Spring Grove on October 18, 2026 featuring a 10K, two 5K options including a corn maze route, a 1-mile family adventure, chip timing, and a finisher medal for every participant.