Trail Running calendar near Cherry Valley 2025-2026

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 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 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 new 10K distance, both of which traverse the beautiful crushed limestone trails of the Danada Forest Preserve. This event..

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 Last Dot Standing event, hosted by Ten Junk Miles, takes place from September 19 to 22, 2025, in Belleville, WI. This unique running challenge requires participants to alternate between running 4.2 miles to Dot's Tavern and back, with a one-hour time limit for each leg. The event continues until..

The Hennepin Hundred is Illinois' only point-to-point, all-trail ultramarathon, taking place along the scenic Hennepin Canal State Trail. This event features multiple race distances, including 100 miles, 50 miles, and a 50K, making it suitable for both seasoned ultrarunners and newcomers. The course..

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..

Among the Trees is a scenic running event scheduled for October 25, 2025, in Dousman, Wisconsin. Participants can choose between two challenging distances: 100k and 50k, both set against the beautiful backdrop of the Southern Kettle Moraine Forest along the historic Ice Age Trail. Runners will start..

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..

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). This themed race, held during deer hunting season, offers participants a fun atmosphere with deer puns and a scenic course pr..

The Quiet Silence 50k is a unique running event taking place in Lake Mills, Wisconsin, on December 5-6, 2025. Participants will have eight hours to complete an out-and-back course on the scenic Glacial Drumlin State Trail, which features a mostly flat, crushed gravel surface. The race begins at Rota..

The Guv'nor Frozen 50K is an ultra-marathon event held in the scenic Driftless Area of Wisconsin, specifically at Governor Dodge State Park. This challenging race offers three distance options: 50K, 25K, and 15K, each featuring a mix of horse trails, dirt paths, and prairie terrain. Participants fac..

The Arctic Frog Run in Libertyville, IL, is an exciting endurance running event featuring multiple race distances: 50K, 25K, 15K, 10K, and 5K. Set against a scenic backdrop, the course includes a mix of pavement, wooded areas, and crushed limestone trails along the Des Plaines River. This unique win..