Wisconsin
Wisconsin Trail Running Calendar 2026-2027
Explore the best trail runs in Wisconsin for 2026-2027! Our updated list features 83 exciting trail runs across the region. Find your next trail run in Wisconsin below and join the trail community at these great events!
December 2026
A progression run on a 443 m indoor track at Pettit National Ice Center on 12/26/2026 where pace increases every three laps until one runner remains.
January 2027
A winter human powered event on the Tuscobia and Wild Rivers State Trails in Northern Wisconsin offering 80 mile one way and 160 mile out and back courses.
Snowshoe races in Cable, WI on January 2, 2027 offering 5 km and 10 km courses with online or mail in registration, a water station on the course, and participant goodie bags.
Live races on January 16, 2027 and virtual self-timed ski and snowshoe events from December 19 to February 14 at MECCA Trails in Mercer, WI.
Winter trail ultramarathon near Palmyra, WI offering a two loop 100K and a new single 50K loop on Ice Age, Whitewater and Scuppernong trails.
A winter trail event in Phillips WI with 10K 5K and 1K options, in person and virtual entries, required snowshoes, limited wool socks, and team divisions.
A winter obstacle race in Lake Geneva with kids courses, fun runs, a 20K Yeti challenge, and a competitive 10K offering cash prizes and age group awards.
A multi-loop cross-country ski marathon and half marathon at Minocqua Winter Park on January 30, 2027, with skate or classic technique and 24K or 48K options.
February 2027
A winter 5 km snowshoe race in Eagle River, Wisconsin on February 6, 2027, held at Ripco Road Park Unit with early and later entry fees and free entry for under 18s.
An annual cross-country ski event at Mt Ashwabay with 15k and 30k classic, skate and skiathlon races plus youth and college divisions and on-course aid.
A classical technique cross-country ski event in Cable, WI on Feb 14, 2027 featuring 12.5 km and 25 km loops plus a Cookie Classic for youth.
A winter timed ultra in the Southern Kettle Moraine Forest offering 6, 12 and 24 hour loop options for solo runners and relay teams. The field is limited to 160 participants and the 6 hour option is available in AM and PM waves.
March 2027
A stair-climbing fundraiser on March 13, 2027 at 411 E Wisconsin Center in Milwaukee, featuring a 30-floor climb and a $100 per person fundraising minimum.
A muddy 5K through maple woods with maple snack stops and a Last Person Standing race where runners repeat a 5K loop with 1000 feet of ascent every hour.
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.
Trail races at Governor Dodge State Park with 50K, 27K and 10K options, cupless aid stations, and organizer policies on registration, safety, and sustainability.
Trail series in Oconomowoc offering 5K, 10K, 13.1 mile, walk and ruck events from April to October 2027; registration opens October 16, 2026.
Annual trail race at the IWSC in Iola, WI offering 5k and 15k courses on new Singletrack trails, a kids 1k if weather permits, plus food and on-site registration.
Three chip-timed races in Belgium, Wisconsin on April 24, 2027, from a flat 5K to a 13.1 mile half marathon with park trails, water stations, T-shirts and a post-race party.