Trail Running calendar near Cherry Valley 2025-2026

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..

ARKTOS is a challenging ultra running event held in Dousman, Wisconsin, featuring 6, 12, and 20-hour race options for solo runners or relay teams of up to four. Set in a quiet, cold forest environment with frozen ground, the race tests participants' endurance and mental toughness in potentially unco..

The Muddy Shamrock @ The Forge is a trail running event held in Lemont, Illinois, featuring a Trail Half Marathon (approximately 13.1 miles) and a Trail Quarter Marathon (about 6.6 miles). The race takes place on wooded single and double-track mountain bike trails, as well as gravel paths around the..

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 Earth Day 50k is a trail running event held in Crystal Lake, Illinois, at Veterans Acres Park. It offers three race distances: 50 kilometers, 15 miles, and 5 miles, all starting together on a 5-mile loop course featuring single track trails and rolling hills. The race emphasizes environmental re..

Childish Nonsense is a trail running event held in Palatine, Illinois, at Deer Grove Forest Preserve West. It offers multiple distances: 10K, 25K, 50K, and 50 miles, with courses consisting of laps on a mostly wide, non-technical trail. Runners encounter a single aid station at the start/finish area..

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 Prickly Pine Jackpot 24 Hour will take place in Dousman from Saturday 2 May 2026 to Sunday 3 May 2026. You can run between 6 and 24 kilometers.

The F^3 Cap Sauers Trail Marathon & 10 Mile is a trail running event held at Teason’s Woods in Palos Hills, Illinois. The marathon features a challenging course on the Sag Valley Trail, consisting of wide horse trails with minimal technical terrain but significant elevation—1050 ft for the marathon..

The Galena Sky Trail Race is an annual trail running event held at Chestnut Mountain Resort in Galena, Illinois, typically on the third weekend of May. The race features challenging, runnable trails winding through ski hills with majestic views of the Mississippi River and neighboring states Iowa an..

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..

Kettle Moraine is a renowned ultra marathon held in LaGrange, Wisconsin, featuring multiple race distances including a 100-mile, 100K, 50K, 38-mile, and a 100-mile relay. Established in 1996, it is one of the oldest 100-mile races in the U.S. The course is 100% trail, with about 65 miles on the scen..