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!
April 2027
Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.
Moonlight Meltdown on April 24, 2027 in Belgium WI features chip timed 5k, 10k and 13.1 courses with scenic park sections and proceeds to local rescue and snowmobile groups.
May 2027
Trail races at Donald County Park offering 5 km, 15 km and a Kids One Mile Fun Run with proceeds supporting Friends of Donald Park for trail maintenance.
Test your endurance at Sylvan Park in Wausau with a backyard ultra format or individual trail loops ranging from 4.167 to 8.334 miles on a scenic and hilly course.
One of the oldest continuously running ultras in the country, Ice Age Trail 50 runs through glacial terrain and offers 50 mile, 50K and half marathon distances.
Rumble on the Ridge is a backyard ultra style last person standing race near Arena, Wisconsin, run on a 1 to 1.25 mile loop with 20 minute laps. The course reverses direction every four hours and includes 250 to 300 feet of elevation gain per lap.
A chip timed 5k run/walk at Wild Mountain Winery on May 16, 2027, with race swag, a wine pour at the finish, and age group awards. The two-lap course runs through vineyards and scenic trails with uneven sections and short steep inclines.
Out-and-back trail event in Belleville, Wisconsin offering 50 mile, 50K, and Half Marathon distances on the Badger and Sugar River rail trails with regular aid stations.
Trail races at Scuppernong Trailhead in Dousman, WI offering 50K, 30K and 10K on a 10K+ loop with an aid station, cupless policy, and proceeds supporting Kettle Moraine projects.
June 2027
Trail run at Crossroads at Big Creek Nature Preserve offering 2K, 5K and 10K routes with chip timing, local prizes, tree giveaways, and race day services.
Two days of long‑distance hiking in Northern Kettle Moraine State Forest offering 20 and 30 mile single loops with aid stations, medals, certificates, and on site parking.
July 2027
Experience the natural beauty of the Kishwauketoe Nature Conservancy in Williams Bay during this annual 5K and kids fun run held on the scenic trail system.
Experience a 10k trail run through High Cliff State Park featuring over 500 feet of elevation gain with rocks and roots across the scenic Sherwood landscape.
Evening trail race at Nine Mile County Forest with 5K, 10K and 20K lap options on single track and ski trails; runners must carry lights.
August 2027
Timed trail event at Pine Mountain on August 8 2027 with loop distances from 2 to 10.8 miles, lift access to the top and a pancake breakfast.
Road and trail runs in Brule, WI on 08/08/2027 offering a 5 mile point to point and a 2 mile out and back walk/run.
A 24 hour event at Nashotah Park with solo and relay options plus a range of fixed distance runs and ruck events, camping and evening activities.
Community run, walk, and bike event at Lake Antoine County Park that raises funds for Special Olympics with paved and unpaved course options.
Community run and walk at Kettle Moraine Lutheran High School featuring a two-loop 5 km, a 2 mile walk, and a 400 m kids run.
October 2027
A timed long distance walking event at Alpine Valley, Elkhorn, WI on October 9, 2027 offering 7, 14, 21, and 28 mile loops, optional weighted vests, and a 10 hour finish limit.