Trail Running calendar near Freeport 2025-2026

The Mines of Spain 100 is a challenging Midwest trail ultramarathon held in Dubuque, Iowa, set in the scenic bluffs, prairies, and forests of the Driftless Region along the Mississippi River valley. The event offers two distances: 100 miles (five loops) and 100 kilometers (three loops) on a roughly..

Soul Crusher is a challenging trail running event held in Crystal Lake, Illinois, offering 5-mile and 10-mile distances. The course, designed by Jeff Lenard, is known as the toughest 5-mile loop in the Midwest, with runners able to complete it once or twice depending on their endurance. The race sta..

The Over The Vines Wine Run/Walk is held at Over the Vines Vineyard & Wine Barn in Edgerton, Wisconsin. This event offers a 5K timed run, a 5K untimed walk, and a 2K untimed walk, all on a scenic trail featuring grass, gravel, and compacted dirt terrain. Participants must be 21 or older and enjoy fo..

The Black Hawk Ridge Trail Run will take place in Mazomanie on Sunday 19 October 2025.

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and picturesque experience amid vibrant fall colors. Both races..

The Miner 49er is an endurance running event held in the scenic Mines of Spain near Dubuque, Iowa. It features two race distances: a 25K out-and-back course with about 2,200 feet of elevation gain, and a 50K race that covers the 25K route twice, totaling approximately 4,400 feet of gain. Runners exp..

The Big Timber XC Challenge is a trail running event held at Camp Big Timber in Elgin, Illinois. Participants can choose between a 3-mile run/walk (one loop) or a 5-mile run (two loops) through a natural wooded area featuring grass, gravel, dirt, and a notable creek crossing with a rope for support...

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or teams of 2 to 4 in relay format. Participants navigate chall..

The Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove, covering a mostly flat, crushed gravel path. Participants h..

The Guv'nor Frozen 50K is a challenging winter ultra-marathon held at Governor Dodge State Park in Dodgeville, Wisconsin. Scheduled for early December, the event offers three distance options: 50K, 25K, and 15K. The courses feature a mix of horse trails, dirt single and double tracks, and prairie pa..

The Frozen Gnome is a challenging winter trail running event held in Crystal Lake, Illinois, at Veteran Acres park. Featuring a "Triple Black Diamond" rated course, the race offers a 50K ultra run, a 10K race, and relay options for teams of two or five. The course consists of a scenic 10K single-tra..

The Whitewalker Ultra 100k is a challenging winter ultramarathon held in Palmyra, Wisconsin, starting at the Emma Carlin Trailhead. Participants complete two 50k loops within 24 hours, traversing the Ice Age Trail to Whitewater and returning, then heading to the Scuppernong Trails and back. The race..

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 cold, wooded environment with frozen ground and brisk winds, the race offers a unique, rugged atmosphere that tests participants'..

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 an eco-friendly..

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 Solo/Relay is an endurance running event held in the scenic Kettle Moraine State Forest near Dousman, Wisconsin. Participants can choose from multiple race options including 6-hour, 12-hour, and 24-hour solo races, as well as 12-hour and 24-hour relays. The course fe..

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..

Rumble on the Ridge is a challenging Last Person Standing ultrarunning event held on a historic dairy farm near Arena, Wisconsin, in the scenic Driftless Area. Participants run a 1 to 1.25-mile loop called "The Drifty Mile," featuring 250-300 feet of elevation gain over mixed terrain including grave..