Trail Running calendar near Galena 2025-2026

Woodpecker Six is a six-hour endurance trail run held in Linn County's scenic Pinicon Ridge Park near Central City, Iowa. The course features a challenging 1.2-mile loop with two significant climbs and multiple stairs, totaling about 215 feet of elevation gain per loop through heavily wooded terrain..

Set in Governor Dodge State Park, The Guv’nor Frozen 50 is Driftless Endurance’s winter ultra featuring 50K, 25K, and 15K options. The 50K is two loops totaling about 31 miles with roughly 4,400 feet of elevation gain, traversing a mix of horse trails, dirt single and double tracks, and prairie path..

The Frozen Assets 5K Run/Walk is a unique winter event held in Madison, Wisconsin, where participants run or walk entirely on the frozen surface of Lake Mendota. The 5K course offers scenic views of downtown Madison and the University of Wisconsin-Madison campus. Starting and finishing at The Edgewa..

The Skunk Ape 806/314 Trail Race, held at Lowell Park in Dixon, Illinois, offers challenging trail running events on March 21, 2026. Participants can choose between a 33.75-mile race to be completed in 8 hours and 6 minutes, a 13.5-mile race with a 3 hour and 14 minute limit, or a relay option. The..

The Donald Dash Trail Run is a popular trail running event held at Donald County Park in Mount Horeb, Wisconsin. It offers two race distances: a 5K for beginners and a more challenging 15K for experienced runners. The course features diverse terrain including prairie, single track, sand, slick bridg..

The Friends of Yellow River State Forest Trail Run/Walk is an annual event held in Harpers Ferry, Iowa, featuring multiple race distances including a family-friendly, fast, and flat 5K on Friday evening, followed by a 5K, 10K, and half marathon on Saturday. The races take place on existing trails wi..

Rumble on the Ridge is a Last Person Standing endurance event held on a private dairy farm in Arena, Wisconsin, in the Driftless Area. Runners tackle The Drifty Mile, a loop of about 1–1.25 miles with at least 250 feet of elevation gain, each loop completed in 20 minutes. The route changes year to y..

Galena Sky Trail Race is held at Chestnut Mountain Resort in Galena, Illinois. It features two timed loop formats: an 8-hour loop and a 4-hour loop on the resort’s trails that climb the same hills skied in winter, offering views of the Mississippi River and the Iowa–Wisconsin shores. The long loop i..

The Sugar Badger 50/50 and Half Marathon is a scenic trail running event held in Belleville, Wisconsin, featuring distances of 50 miles, 50 kilometers, and a half marathon. The course follows the flat, soft rail trails of the Badger State Trail and Sugar River State Trail, showcasing trestle bridges..