Trail Running calendar near Portage 2025-2026

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 held at Kankakee Community College in Kankakee, Illinois. This donut-themed event features a 5K Donut Dash and a shorter 2K Sprinkle Sprint, both designed for participants of all ages, including children under 12 who can join for free. The course..

The Hickory Knolls Trail Run, held at Hickory Knolls Nature Area in St. Charles, Illinois, offers 5K and 10K individual races plus a 10K two-person relay. The course features a scenic, approximately 3-mile loop of grass, dirt, and gravel trails with a mix of flat sections and hills, set in a diverse..

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 Jennie Hamilton Memorial 5 Mile Trail Run is held at Stoney Run County Park in Hebron, Indiana. This challenging trail race features a 5-mile course marked with flags and arrow signs at major turns. Runners may encounter mud, bugs, and a pond crossing near the end, with an optional detour adding..

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 an annual running event held in Wheaton, Illinois, at the scenic Danada Forest Preserve. Scheduled for September 6, 2025, the race offers both half marathon and 10K distances, including virtual options. The course is USATF certified, featuring a flat and..

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..

Half Day at the Lake is a unique 6- and 12-hour ultramarathon held in Evanston, Illinois, along a scenic 2-mile loop on Chicago’s north shore lakefront path. The course features paved and crushed gravel surfaces, passing through Evanston’s lakefront and Northwestern University’s campus, offering bea..

The Tryon Farm 50k is a trail running event held at Tryon Farm in Michigan City, Indiana. The course features an 8-loop 4-mile trail that includes open grassy fields, single-track dirt trails, and small pavement sections connecting different parts of the trail system. The event offers multiple dista..

The Des Plaines River Trail Races, held in Lake County, Illinois, offer a scenic and fast trail running experience with distances including a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Starting and finishing at Half Day Forest Preserve, the course features a flat, wide, crus..

The St. Pats 24 Hour Race is a unique running event held at St. Patrick's County Park in South Bend, Indiana.Participants can choose between 12 and 24-hour races, navigating scenic dirt and grass trails with minimal asphalt sections. The event offers amenities such as overnight accommodations, showe..

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 cho..

The Forge Trail Run Festival, scheduled for November 15, 2025, in Lemont, IL, features a variety of trail running events including 10K, 20K (Half Marathon), 30K, and 60K races. Participants will navigate single and double-track trails through scenic woods and gravel paths around the historic Lemont..

The Bigfoot Half Trail Run is a half marathon trail race held at Stoney Run County Park in Hebron, Indiana. Participants complete the distance by running two loops around the park. The course features two aid stations: a manned station at the start/finish area and an unmanned station approximately 3..

The Arctic Frog Run in Libertyville, IL, is a beginner-friendly endurance race featuring multiple distances, including 50K, 25K, 15K, 10K, and 5K. The scenic course combines pavement, wooded trails, and crushed limestone paths along the Des Plaines River and Northwest Casey Trails. Participants can..