Trail Running calendar near Irving Park 2025-2026

XTERRA DINO Northern Indiana is an off-road multisport event held in South Bend, Indiana, near Chicago. 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 kayak triathlon. The course is known for bei..

The Dino South Bend Trail Run, known as the XTERRA Dino 7K Trail Run, takes place at Potato Creek State Park in South Bend, Indiana. This 7-kilometer race features a lollipop loop course with wide, stable paths suitable for both beginners and speed-focused runners. The course includes two challengin..

The Trail Golf Endurance Challenge, held in Valparaiso, Indiana, is a unique trail running event featuring distances of 50K, 50K relay, 10 miles, and 10-mile relay. Unlike traditional races, it uses a golf-style scoring system where runners complete 3-4 mile "holes" each hour, aiming for the lowest..

The Kishwauketoe 5K Cross Country Run takes place in Williams Bay, Wisconsin, starting at the KNC entrance on Highway 67. The course features scenic grass trails through hills, woods, and prairie, offering a natural and challenging terrain for runners. The event includes a 5K run/walk and a children..

The Jennie Hamilton Memorial 5 Mile Trail Run is held at Stoney Run County Park in Hebron, Indiana. This trail race features a challenging 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..

The Oakadoke Trail Runs, held in Valparaiso, Indiana, is a summer trail running event featuring challenging courses through the scenic Creekside Trails. Participants can choose from three distances: 18 miles (two loops), 9 miles (one full loop), and 4 miles (half loop focusing on the Salt Creek sect..

The Summer Trail Classic is a trail running event held at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. It offers three race distances: approximately 4 miles, 9.5 miles, and 13 miles, featuring twisting single-track trails that provide a true trail running experience. The event is part..

The Chupacabra Endurance Run is a 10-hour endurance race held at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants run multiple loops of a 3.4-3.5 mile trail with minimal pavement, completing each loop within one hour to avoid elimination. The event..

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, set for September 6, 2025. Participants can choose between a USATF-certified half marathon or 10K race, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on crushe..

The Hobo Trail Runs, hosted by Rockford Road Runners, take place at Rock Cut State Park in Rockford, Illinois. This annual event offers multiple trail running distances including 10k, 25k, and 50k races, with options to participate in single races or the challenging Triple Crown series (85k total) o..

Timely Nonsense is a unique timed running event held in Chicago, IL, at a 58-acre park located at California and Montrose. Participants run a 0.75-mile paved loop for either 6 or 12 hours, with an aid station at the start/finish offering typical ultrarunning fare and additional vendor treats like ho..

Half Day at the Lake is a unique 6- or 12-hour ultra-running event held in Evanston, Illinois, along a scenic 2-mile loop on the lakefront path near Northwestern University. The course features a mix of paved and crushed gravel surfaces, offering beautiful views of the Chicago skyline and the north..

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 circuit through a mix of open grassy fields, single-track dirt trails, and small pavement sections connecting different trail areas. The event also offers shorter distances..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

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, held at St. Patrick's County Park in South Bend, Indiana, is a premier timed trail running event featuring 12- and 24-hour race options.Participants run primarily on scenic dirt and grass trails with brief asphalt crossings, enjoying a challenging yet picturesque course. T..

Soul Crusher is a challenging trail running event held in Crystal Lake, Illinois, offering 5-mile and 10-mile distances. The course, designed by Jeff Lenard, is known as the toughest 5-mile loop in the Midwest, with runners able to complete one or two loops depending on their endurance. The race sta..

The Buckley 5 Miler is a scenic and challenging cross-country trail race held at the Buckley Homestead in Lowell, Indiana. The 5-mile course features a 2-mile loop on the north side of the park followed by a 3-mile loop through the park, finishing at the pioneer farm. Runners encounter a picturesque..

The Fancy Nonsense 25K/50K is a whimsical ultramarathon held in the Palos Trail System near Willow Springs and Lemont, Illinois, about 20 minutes from downtown Chicago. Runners can choose from 25K, 50K, or 5-mile distances on a mostly single-track, 5.5-mile loop course that starts and finishes at Re..

The Fast Track Cross Country Open is a 3-mile cross country running event held in Schaumburg, Illinois, on the MacNider course near Hoover Elementary School. Open to all ages and abilities, the event features separate women's and men's races. Participants can enjoy running on grass and have the opti..