Trail Running calendar near Madison 2026-2027

Event Overview Tour de Trails is a series of four winter trail runs held on Saturdays from December 2025 to March 2026. Each race is held at a different forest preserve or park in the Rockford, Illinois area. Participants can register for i..

The Fight for Air Stair Climb returns to Milwaukee's 411 East Wisconsin Center on March 21, 2026. Participants can choose to climb the 30-story building once, twice, or take on the Power Hour challenge. A virtual option is also available fo..

Join a long-standing Waukesha tradition featuring marathon and shorter distances plus new rucking categories. Support local parks while enjoying a professionally managed event on scenic city trails.

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

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.

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.

Rumble on the Ridge is a backyard ultra held on a private farm near Madison. Runners tackle a secret 1+ mile loop every 20 minutes until only one remains. The event supports the creation of a new local trail network.

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.

The Sugar Badger 50 Miles is a trail ultramarathon scheduled for May 2026. Organized by Ten Junk Miles Racing, it focuses on a community atmosphere on the trails. The event is a single 50-mile distance challenge.

Test your grit at Byron Motosports Park with tactical obstacle courses ranging from 5K to 10K endurance laps. Choose from elite vest challenges, weighted rucking, or open waves designed to honor the resilience of first responders.

A trail run at Blue Mound State Park on June 6, 2026 offering 10K and 18K courses over varied single-track and ski trails; proceeds benefit the Friends of Blue Mound State Park.

Experience one of the oldest 100 mile races in the US on the scenic Ice Age Trail. This all-trail event offers distances from 38 miles to a 100 mile Western States qualifier in the heart of Wisconsin.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

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.

Experience the Savage Race in Spring Grove with obstacles and mud across multiple distances. Choose between a five to seven mile course or the shorter three mile Blitz for an engaging outdoor fitness experience.

Event Overview The DWD Devil's Lake is a trail running event scheduled for July 11, 2026. It takes place at Devil's Lake, an area noted for its geological features formed in the ice age. The event is located in Baraboo, Wisconsin, just nort..

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

Challenge yourself on the scenic trails of Iowa's Mines of Spain with 4-mile, 7-mile, and half marathon races. The courses feature a mix of prairie paths, forest tracks, and blufftop views. Proceeds support local trail conservation.