Wisconsin
Wisconsin Trail Running Calendar 2026-2027
Explore the best trail runs in Wisconsin for 2026-2027! Our updated list features 82 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 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 family friendly fundraiser at Petrifying Springs Park offering 1 mile and 2.25 mile options to support Rey de Reyes Ministry in Guatemala with virtual participation available.
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 through Black River State Forest on October 17 2026 with 10k, 25k, 50k and a combined 85k that has a 12 hour 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.
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.
Timed trail challenge at Whitetail Ridge, River Falls WI offering 4 hour or 8 hour options on a 5 mile single track loop with a final hour 1 mile bonus loop.
Trail event at Peninsula State Park with 30K and 14K courses, finish at Welcker's Point, post-race food and proceeds for park trail maintenance.
The 14th annual Frosty Rock Challenge in Fort Atkinson offers a 12k, a 5k and a free 1 mile walk run with proceeds supporting local and international Rotary projects.