Trail Running calendar near Libertyville 2024-2025

The Kettle Moraine 100 Endurance Races is a premier ultra marathon event held in the scenic Kettle Moraine region, featuring a variety of race distances including 100 miles, 100k, 50k, and 38 miles. Established in 1996, this trail race showcases the beautiful Ice Age Trail, with 65 miles of the cour..

The Whitewater Trail Challenge is an exciting running event taking place on June 21, 2025, in Whitewater, Wisconsin. Participants can choose from three race distances: a 10K, a half marathon, and a 50K, all set against the stunning backdrop of the Ice Age Trail, a 1,200-mile scenic footpath. The cou..

The Jennie Hamilton Memorial 5 Mile Trail Run is set to take place at Stoney Run County Park in Hebron, Indiana. This event is part of the Crazy Legs Race Series, which aims to promote trail running in the Northwest Indiana region. Participants can expect a challenging course with features such as m..

The Oakadoke Trail Runs is a summer trail running event held in Valparaiso, IN, featuring scenic courses of 18 miles, 9 miles, and 4 miles through the picturesque Creekside Trails. Participants can enjoy a challenging yet enjoyable experience with tree-covered single-track paths, winding switchbacks..

The Chupacabra Endurance Run is a 10-hour race taking place at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants will tackle a loop of 4.1-4.2 miles, consisting of both pavement and single-track trails, with the challenge of completing each loop wit..

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 compete 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 loo..

The Tryon Farm 50k is part of a multi-distance running event that includes a 4 Miler, 8 Miler, 25k, and a 2-mile Fun Run/Walk, taking place at Tryon Farm in Michigan City, Indiana. The course features a scenic 4-mile loop through the farm, combining grassy fields, dirt trails, and minimal pavement. ..

The Fancy Nonsense 25K/50K is a whimsical running event held in Lemont, IL, designed to bring joy and laughter to participants. Set in the scenic Palos Trail System, the race features a 5.5-mile loop course primarily on single track trails. Runners can choose between 25K and 50K distances, with aid ..

The Forge Trail Run Festival is an exciting trail running event taking place in Lemont, Illinois. Scheduled for November 15, 2025, the festival features multiple race distances, including a 10K, 20K (Half Marathon), 30K, and 60K. Participants will navigate through scenic single and double-track trai..

The Bucks & Does 13.1 Pointer is a running event taking place in Nashotah, Wisconsin, featuring multiple race distances including a 5K, 10K, and a half marathon (13.1 miles). Scheduled for November 15, 2025, this event embraces a deer-themed atmosphere, coinciding with Wisconsin's deer hunting seaso..