Wisconsin
Wisconsin Trail Running Calendar 2026-2027
Explore the best trail runs in Wisconsin for 2026-2027! Our updated list features 75 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 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.
Community running, rucking, and family walking event on October 10, 2026 in Oconomowoc, with proceeds supporting children with special needs.
Six, 12 and 20 hour trail ultras in the Southern Kettle Moraine Forest with three loop options, solo or relay teams, and a village basecamp.
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.
Looped fundraising run and walk at Another Chance Ranch in Neosho, WI offering distances from a few miles to a marathon and beyond, with a $35 registration donation.
A community fundraiser on October 10, 2026 at Petrifying Springs Park benefiting Rey de Reyes Ministry, with in-person trail distances and a virtual participation option.
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 in Black River State Forest offering 10k, 25k, 50k and a combined 85k with on site camping and a 12 hour cutoff for the 85k.
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 of 25K, 10K and 5K at Iola Winter Sports Club on October 17, 2026 with on-course aid for longer routes and awards for top finishers.
A trail running event on October 18, 2026 at the Black Hawk Unit in Mazomanie offering 8K and 16K distances in support of Groundswell Conservancy.
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.
A community 5K trail run at Minocqua Winter Park raising funds for the park and the Lakeland Union High School cross country team.
Experience a festive 5K trail run through Baldwin featuring bonfires and s’mores with costumes highly encouraged for all participants.
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.
October running event at Optimist Community Park in Janesville offering 1 mile and 5K courses with proceeds to Momentum Track and Cross Country Club.
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.