Wisconsin
Wisconsin Trail Running Calendar 2026-2027
Explore the best trail runs in Wisconsin for 2026-2027! Our updated list features 86 exciting trail runs across the region. Find your next trail run in Wisconsin below and join the trail community at these great events!
October 2026
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-country pro..
Community 5K at Torpy Park in Minocqua supporting the Minocqua Professional Police Association with medals for top finishers and a cops and robbers costume theme.
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.
A 10 miles trail race at Willow River State Park with technical single track, climbs, stairs, a waterfall, and a cupless format with one aid station.
Looped trail race in Dodgeville Wisconsin with 50K, 20 mile and 10 mile options across rocky singletrack, ridgelines and fully stocked aid stations.
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.
Trail races of 10k, 25k, 50k and an 85k combined course through Black River State Forest, with camping and finish line food.
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.
Trail races at Iola Winter Sports Club on 10/17/2026 offering 25K, 10K and 5K with on course aid, post race refreshments and age group awards.
An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.
Hixon 50 is a two-day trail running weekend in Hixon Forest near La Crosse, Wisconsin. It offers races from a kids event and 5K and 10K up to 25K and 50K on singletrack with Mississippi River Valley views.
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.
Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.
November 2026
A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.
Timed trail challenge at Whitetail Ridge: choose a four hour or eight hour run on a 5 mile single track loop with a one mile bonus.
Trail runs of 30K and 14K through Peninsula State Park with on-course support, bluffs, and food and beverages at the finish.
A community running event at Fort Atkinson High School featuring a 12K mixed terrain route, a 5K on neighborhood streets, and a 1 mile untimed walk/run, with overall and age group awards for the 5K and 12K.