Trail Running calendar near Wheaton 2025-2026

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 Kishwauketoe 5K Cross Country Run is an exciting running event taking place at the Kishwauketoe Nature Conservancy in Williams Bay, Wisconsin. The event features a 5K run/walk and a children's 1/4 mile walk/run, making it accessible for participants of all ages. The course winds through scenic g..

The Pinetum Mind Games Endurance Event is an exciting running challenge held at Lowell Park in Dixon, IL. Participants can choose to compete in 6, 12, or 24-hour formats, either solo or as part of a relay team. The course consists of a .411-mile loop designed to test mental and physical endurance, e..

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, Indiana, featuring three race distances: 18 miles, 9 miles, and 4 miles. Participants will navigate scenic, tree-covered single-track trails with various elevations and terrain challenges, including winding switchbacks and c..

The Chupacabra Trail Races, taking place in Dixon, IL, offers participants a unique night running experience on August 9, 2025. Runners can choose from three distances: 5 miles, 10 miles, or 15 miles, with a loop course that combines grass, gravel, and dirt trails. The event features a single aid st..

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 Run is a new event in the Crazy Legs Race Series, scheduled for August 30, 2025, at Bluhm County Park in Westville, Indiana. This 10-hour endurance race challenges participants to complete a loop of 4.1-4.2 miles, consisting of both pavement and single-track trails, within o..

The Naperville Trails Half Marathon and 10K is an annual running event held in Wheaton, Illinois, featuring a scenic course through the Danada Forest Preserve. Participants can choose between a half marathon or a new 10K distance, both of which are USATF certified. The event celebrates its 15th anni..

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, with options for 2 or 4-person teams. The race is set in a scenic 58-acre park, where runners will navigate a ..

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 Des Plaines River Trail Races feature a variety of endurance events, including a Half Marathon, Marathon, 50K, and 50 Mile race, all set along the scenic Des Plaines River Trail in Lake County, Illinois. Participants will enjoy a flat, wide, crushed gravel trail that meanders through lush forest..

The Fancy Nonsense 25K/50K is a whimsical running event designed to bring joy and laughter to participants while challenging their physical and mental limits. Set in the scenic Palos Trail System near Chicago, the race features a 5.5-mile loop course primarily on single track trails. Runners can enj..

The Forge Trail Run Festival is an exciting trail running event held in Lemont, Illinois, featuring a variety of race distances including a 4 Mile(ish), 10K, 20K (Half Marathon), and 30K. Participants will navigate through scenic single and double-track trails, experiencing the natural terrain of th..