Trail Running Calendar Wisconsin 2026-2027

Tackle a 1.5-mile farm-themed obstacle course at Heim's Hillcrest Dairy. The event features challenges like feeding calves, flipping tires, and climbing hay bales. Afterwards, enjoy a yogurt bar and an optional farm tour.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

The Trout Brook 10 miler is a trail race at Willow River State Park in Hudson WI, featuring single-track trails, hills, a stair climb, and waterfall views with an aid station near the halfway point.

Trail runs on a looped Driftless Area course near Dodgeville, Wisconsin, with 50K, 20 mile and 10 mile options, technical terrain, two aid stations per loop and on course support.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

Join the charity trail run or walk in Denmark, Wisconsin. Choose your distance for canicross with your dog or go solo on the wooded trails. The event includes a costume contest and supports the Crisis Cafe.

Run scenic glaciated woodlands and rolling ridges at the Black River Trail Classic in Millston WI with options from 10k to the 85k ultra. Expect well marked trails, hot finish line food, a winter hat and wooden finisher medals.

A point-to-point 50 mile road ultramarathon in Door County, WI on October 24, 2026, from Gills Rock to Sturgeon Bay. Solo runners have a 12 hour limit, dedicated aid tents, multiple drop bag exchanges, and a finisher tent plus post‑race par..

Experience a scenic trail running weekend in Hixon Forest featuring distances from a 5k to a 50k ultra. Run through rugged singletrack and rolling bluffs with views of the Mississippi River Valley.

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.

A trail run and celebration in Peninsula State Park on November 7, 2026. The event features a 30K option, race hoodies, on course support, post race beer from Sway Brewing, and contributions to Friends of Peninsula State Park.

The Red Yeti Rampage is a fall trail run at Tower Ridge in Eau Claire. Choose from 5K, 10K, or the new 15K Yeti Challenge, all starting at the Chalet. A post-race lunch, awards, and refreshments are included.

A last runner standing race at Palmer's Landing where runners complete a one mile out and back on the North Country Trail every 15 minutes until they cannot finish a lap. The event raises funds for the Brule St. Croix Chapter.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

A winter trail event at Governor Dodge State Park on Dec 5, 2026 offering 50K, 25K and 15K over horse trails, single and double track with multiple aid stations, cup-less hydration, and specific pacer and crewing rules for the 50K.

A dog friendly trail running event at Lake Geneva Ziplines and Adventures with a 4 mile loop, an 8 mile option, and a focus on Canicross. Awards are reserved for teams running with dogs and all finishers receive a small gift.

Experience a unique winter obstacle course in Lake Geneva featuring distances from 5K to 20K. Enjoy a festival atmosphere with fire pits and food trucks after conquering challenges designed for both fun and competitive athletes.

Experience a unique 5K race held entirely on the frozen surface of Lake Mendota. Participants can run walk or skate across the ice while enjoying scenic views of downtown Madison and the university campus.