Trail Running calendar near Madison 2026-2027

A trail race at Donald County Park in Mount Horeb on May 2, 2026, offering 5 km, 15 km and a Kids One Mile Fun Run; chip timing, aid stations, awards, and proceeds benefit Friends of Donald Park for trail maintenance.

The Prickly Pine Jackpot 24 Hour offers timed running events in the scenic Kettle Moraine State Forest. Runners choose from three different loop distances to build their mileage, with cash jackpots for top solo and relay finishers. Amenitie..

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

Trail run in Dubuque on May 2, 2026 offering 5K, 10K and half marathon distances. The event features marked trails, basic timing, a custom bib, a rotating race item, and post-race food; series entry includes a series gift.

A long running Wisconsin trail ultramarathon that winds through forests, rocky ridges and glacial landforms. The event offers 50 miles, 50K and a half marathon and typically sells out quickly.

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 8 hour and 4 hour loop trail events at Chestnut Mountain Resort near Galena, Illinois, with 2.91 and 0.6 mile loops, timing-based mileage awards, a finisher medal, and an on-site meal and after party.

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

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..

Rail-trail event in Belleville, WI using the Badger State Trail and Sugar River State Trail. Distances include 50 miles, 50K and a half marathon on flat, soft surfaces with trestle bridges and a quarter mile tunnel.

Frontline OCR at Byron Motosports Park on May 23, 2026 offers 10K and 5K obstacle courses, a ruck division, a kids mile, Special Forces and Heroes waves, plus team entry packs, organized by a 501(c)(3) foundation.

Experience an inclusive trail running event at Richard Bong State Recreation Area. Choose from five different timed options ranging from three to twenty four hours on a scenic course with rolling hills.

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.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group 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.