Trail Running calendar near Libertyville 2025-2026

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 Kettle Moraine 100 Endurance Trail Races, held annually in June in the Southern Kettles of Wisconsin, offer challenging ultra-distance events including 100-mile, 100k, 50k, and 38-mile races. Established in 1996, the course is predominantly trail-based, with about 65 miles running along the scen..

The Whitewater Trail Challenge, held in Whitewater, Wisconsin, is a scenic trail running event set along a portion of the iconic Ice Age Trail. This National Scenic Trail showcases the glacially sculpted landscape of Wisconsin with rolling hills and well-established trails. The event offers three ra..

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 Gristmill Grind 10K is a challenging trail race held annually at Franklin Creek State Park in Franklin Grove, Illinois. Known as one of the most difficult 10Ks in the area, the course features technical trails with approximately 800 feet of elevation gain, multiple hills, and four creek crossing..

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..

The Tiger 10 Miler is an annual trail race held in Byron, Illinois, featuring a challenging 10-mile course through the scenic Byron Forest Preserve and Nardi Equine Prairie. Participants receive a custom finisher's medal, a race shirt, and have the chance to win awards in various age categories. The..

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 Lapham Peak Colorama Run/Walk is an annual fall running event held at Lapham Peak State Forest in Delafield, Wisconsin. Celebrating its 36th year in 2025, the event features 5K and 10K courses on wide, well-groomed ski and hiking trails, with the 5K covering the park's middle level and the 10K f..

Zachariah's Acres Fall Run, Walk & Roll is a charitable event taking place in Oconomowoc, WI, designed to support children with special needs. The event features a 5K, a half marathon, and a family-friendly walk and roll, all set against the backdrop of 125 acres of beautiful natural scenery. Partic..

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..

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..