Trail Running calendar near Libertyville 2025-2026

The Dig the Dunes Beer Run will take place in Michigan City on Thursday 1 May 2025.

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting endurance running event taking place in the scenic Kettle Moraine State Forest. Participants can choose from various race formats, including 6-hour, 12-hour, and 24-hour solo or relay options. The course features three unique loops of differ..

The Great Western Half-Marathon & 10K, organized by Fox River Trail Runners, is a popular race held annually on the scenic Great Western Trail. With a history spanning over 25 years, the event features a flat, out-and-back course that attracts runners of all levels. Participants can choose between t..

The F^3 Cap Sauers Trail Marathon & 10 Mile is set to take place in Palos Hills, IL, on May 10, 2025. This event features a challenging marathon and a 10-mile race, both traversing the scenic Cap Sauers Holding Nature Preserve, the largest undeveloped area in Cook County. Participants will experienc..

The Wildflower Run is an exciting running event taking place in Bristol, Wisconsin, featuring a 4.5-mile trail run and a 2-mile fun run/hike through the scenic Bristol Woods County Park. Scheduled for the third Saturday in May, the event coincides with peak wildflower viewing, making it a beautiful..

The Chicago 7-11 Hour Endurance Run, organized by Yeti Trail Runners, is a unique trail running event set in Willow Springs, IL. Participants can choose between a 7-hour or 11-hour endurance challenge, navigating a scenic 4-mile loop through the picturesque Wolf Road Woods and Palos Preserves. The e..

Trail Run Xtreme is an exciting trail running event held in Portage, Indiana, featuring a challenging 12K trail race and a 3K kids race. Participants can expect a rugged course filled with roots, hills, and mud, designed to test their endurance and spirit. The event promotes camaraderie among runner..

Bong Backyards is an ultramarathon event held at Richard Bong State Recreation Area in Brighton, Wisconsin, on June 6, 2025. The event offers multiple race distances, including the Backyard Ultra and Backyard 24, catering to runners of all skill levels. Participants can enjoy scenic trails, rolling..

The Hickory Knolls Trail Run, taking place on June 8, 2025, at the Hickory Knolls Discovery Center in St. Charles, IL, features a 5K, 10K, and a 10K relay event. Participants can enjoy a scenic course that includes grass and dirt trails, with a mix of flat sections and hills.The event is part of the..

The Kettle Moraine 100 Endurance Races is a premier ultra marathon event held annually in June, featuring a variety of race distances including 100 miles, 100 kilometers, 50 kilometers, and 38 miles. Established in 1996, this trail race showcases the scenic beauty of the Kettle Moraine region, with..

The Whitewater Trail Challenge is a scenic trail running event held in Whitewater, Wisconsin, along a portion of the iconic Ice Age Trail. This National Scenic Trail showcases the glacially sculpted landscape of the region. The event offers three race distances: 10K, half marathon (21K), and 50K, fe..

The Trail Golf Endurance Challenge is a unique trail running event held in Valparaiso, Indiana, featuring distances of 50K, 10 miles, and relay options. Inspired by golf, participants complete a series of 3-4 mile routes called "holes," starting at the top of each hour. Runners aim for the lowest cu..

The Kishwauketoe 5K Cross Country Run is a community-focused running event taking place in Williams Bay, Wisconsin. Participants can choose between a 5K run/walk and a children's 1/4 mile walk/run for ages 10 and under. The course features scenic grass trails through hills, woods, and prairie, with..

The Jennie Hamilton Memorial 5 Mile Trail Run is held at Stoney Run County Park in Hebron, Indiana. This challenging trail race features a marked course with flags and arrows at major turns, including natural obstacles such as mud, bugs, and a pond crossing near the end, with a detour option availab..

Oakadoke Trail Runs, held in Valparaiso, Indiana, offers scenic trail racing through Creekside Trails featuring tree-covered single-track, switchbacks, creek crossings, and farmland views. The event includes three distances: 18 miles, 9 miles, and 4 miles, with start times in the morning. The challe..

The Gristmill Grind 10K is an annual trail race held at Franklin Creek State Parks Natural Area, known for its challenging terrain and scenic views. Scheduled for August 30, 2025, this event features a 10K race with significant elevation changes and creek crossings, as well as a 1-mile walk. Partici..

The Chupacabra Endurance 10-hour Run, part of the Crazy Legs Race Series, takes place at Bluhm County Park in Westville, Indiana. This challenging event features a 3.4-3.5 mile trail loop with minimal pavement, which runners must complete within one hour per loop to continue. The race lasts 10 hours..

The Naperville Trails Half Marathon & 10K is a scenic running event taking place in Wheaton, Illinois, on September 6, 2025. Participants can choose between a half marathon and a newly introduced 10K distance, both of which traverse the beautiful crushed limestone trails of the Danada Forest Preserv..

Timely Nonsense is a unique running event taking place in Chicago, IL, featuring both 6-hour and 12-hour timed races. Participants can choose to run individually or as part of a relay team of two or four. The race is set in a scenic 58-acre park, where runners will navigate a 0.75-mile paved loop.Ea..

The Tiger 10 Miler is an annual trail race held in Byron, Illinois, featuring a challenging 10-mile course through the scenic Byron Forest Preserve and Nardi Equine Prairie. Participants receive a custom finisher's medal, a race shirt, and have the chance to win awards in various age categories. The..