Wisconsin
Wisconsin Trail Running Calendar 2026-2027
Explore the best trail runs in Wisconsin for 2026-2027! Our updated list features 78 exciting trail runs across the region. Find your next trail run in Wisconsin below and join the trail community at these great events!
September 2026
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.
October 2026
Trail running and a guided perimeter walk at Rock River Heritage County Park with a timed 5K using chip timing and a heritage celebration with food trucks and live music.
Explore the scenic trails and steep hills of Mirror Lake State Park with several distances available. Finish your race with refreshments and s'mores around a campfire while supporting local park projects.
A farm based obstacle course at Heim's Hillcrest Dairy in Algoma covers about 1.5 miles with tasks such as feeding calves and climbing over hay bales. Registration opens July 1 with an early price of $20 until September 1.
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 with a virtual option at Glacier Creek Middle School on October 3, 2026, featuring packet pickup, awards, live timing, and local fundraising.
A community 5K run and walk in Minocqua hosted by the local police association to raise funds for youth and family programs.
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.