Trail Running calendar near Cross Plains 2026-2027

A Last Person Standing ultrarun on a farm near Arena, WI, run on a 1 to 1.25 mile loop with about 250 to 300 feet of climbing per lap. The course changes yearly, reverses every four hours, and continues until one runner remains.

Timed four-hour and eight-hour loop trail races at Chestnut Mountain Resort with scenic river views, looped laps, post-race music and meal, included shirt and finisher medal, and awards for mileage and costumes.

A low-impact, no-frills running event on May 16, 2026 in Delafield, Wisconsin offering distances from a 1K kids run to a half marathon, timed by a professional crew with proceeds supporting Tall Pines Conservancy.

Big Climb Wisconsin on May 16, 2026 in Madison is a team-based stadium climb that features stairs, ramps, and concourses. The event honors patients and survivors and awards participants a finisher medal while supporting efforts against bloo..

An out and back on the Badger State and Sugar River rail trails in Belleville, WI on May 23, 2026, offering 50 mile, 50K and half marathon options with aid stations, photos, pizza and beer provided.

A multiwave obstacle course at Byron Motosports Park offering 10K, 5K, ruck, and kids divisions, with Special Forces and Endurance competitive formats and team entry packs available.

Blue Mound Trail Run on June 6, 2026 in Blue Mound State Park features 10K and 18K trail races on single-track and ski trails, and serves as a fundraiser for Friends of Blue Mound State Park.

An annual June endurance trail event featuring 100 mile, 100k, 50k and 38 mile options on mainly Ice Age Trail terrain. Entry for 2026 is by lottery with an ordered waitlist and early invites for rollovers and volunteers.

A Spartan Trail event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 50K, half marathon and 10K, and the trail terrain ranges from smooth to technical.

An overnight timed 10 hour trail run at Millville Bridle Unit in Prairie du Chien, WI, on a 5.25 mile loop. Limited to 75 runners with one aid station and an emphasis on a joyful, supportive, inclusive atmosphere.

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

A trail running event at Devil's Lake near Baraboo, WI on July 11, 2026, offering distances from 10K to 50 miles, marked courses with aid, post-race food and a finisher medal.

A prairie trail run and walk at Lapham Peak State Forest on July 11, 2026 that raises funds for prairie management, offers awards and shirts for early participants, and includes merchandise, seed sales and on-site food.

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

MSRC XC 5k Classic is a cross country race at Verona Area High School on July 12, 2026. It includes a 5k and a 1.6 mile kids race, team scoring for teams of five runners, and awards across multiple age and team categories.

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

Experience the natural beauty of Dubuque with trail races through the Mines of Spain Recreation Area. Enjoy distances ranging from 4 miles to a half marathon followed by a post race party with brick oven pizza and local beer.

Test your endurance at Prairie du Chien's first backyard ultra featuring a 4.167 mile trail loop through La Riviere Park. Run one lap every hour until only one participant remains or enjoy a relaxed one lap fun run.

A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.

Trail races at New Glarus Woods State Park on August 15, 2026 include 16K, 8K, 5K and a free 1K kids run. Proceeds benefit Friends of New Glarus Woods State Park and awards include age-group prizes plus a 16K consistency award.