Trail Running calendar near Irving Park 2025-2026

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..

Bong Backyards is an exciting trail and ultra running event held at the scenic Richard Bong State Recreation Area in Brighton, Wisconsin. Scheduled for June 6, 2025, it offers multiple race distances, including the challenging Backyard Ultra and the Backyard 24, catering to runners of all skill leve..

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

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 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 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 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 at Twin Creeks Farm in Valparaiso, Indiana, offer a scenic and challenging summer trail running experience. Participants can choose from 18-mile, 9-mile, or 4-mile distances, with courses featuring tree-covered single-track trails, winding switchbacks, farmland views, a..

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, 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 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 ultra running fare and additional vendor treats like h..

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 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 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 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 encourages joy and imagin..

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..