Trail Running calendar near Irving Park 2025-2026

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

The Run Happy 50K, along with other distances, is set to take place on May 3, 2025, at Potato Creek State Park Nature Center in North Liberty, Indiana. This event caters to both walkers and runners, making it ideal for families who wish to participate in various distances together. The course featur..

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..

Glazin' the Trail is a family-friendly run/walk event taking place at Kankakee Community College in Illinois. Scheduled for May 31, 2025, this fun-filled morning features a donut-themed atmosphere, encouraging participants to enjoy the scenic trails along the Kankakee River. The event includes a 5K..

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 Dino South Bend Trail Run is a 7-kilometer race held at Potato Creek State Park in Indiana. The course features wide, stable paths suitable for runners of all levels, with a mix of easy terrain and two challenging hills that test endurance. Participants can earn bonus points toward the Dino Trai..

XTERRA DINO Northern Indiana is an off-road multisport event held in South Bend, Indiana, and part of the XTERRA World Tour. It offers a variety of races including a full-distance triathlon (800m swim, 24K bike, 7K run), duathlon, trail run, and a kayak triathlon, suitable for individuals and relay..

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 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 Half Day at the Lake is an exciting running event taking place in Evanston, IL, featuring both 12-hour and 6-hour races. Set along a scenic 2-mile loop by the lakefront and Northwestern University, this race caters to all experience levels, from seasoned ultra-runners to first-timers. Participan..