Trail Running calendar near Libertyville 2025-2026

The Tombstone 30k/50k Trail Run is an exciting trail running event taking place at Sunset Hill Farm County Park in Valparaiso, Indiana. Scheduled for March 8, 2025, participants can choose between two distances: 30k and 50k. The course features challenging loops, including the famous "Roller Coaster..

The Muddy Shamrock @ The Forge is an exciting trail running event taking place in Lemont, Illinois, featuring a Trail Half Marathon and a Trail Quarter Marathon. Set against the scenic backdrop of the historic Lemont Quarries, participants will navigate through wooded single and double-track trails,..

The False Spring Trail Runs is a challenging trail race held at Soldiers Memorial Park in LaPorte, Indiana. Participants can choose between a 10K and a Half Marathon, with the course featuring scenic woodsy single-track trails, winding switchbacks, and views of lakes and ponds. The event is known fo..

The Forrest Gump Hump 5K Trail Run is scheduled to take place at Oak Ridge Prairie and Oak Savannah Trail in Griffith, Indiana. This event, organized by the Crazy Legs Race Series, promotes non-pavement races in the Northwest Indiana region. Participants can expect a fun and challenging course, with..

The Trailbreaker is an annual running event held in Waukesha, Wisconsin, since 1993, featuring a variety of races including a Marathon, Half Marathon, 10K, 5K, Walk, and a Kiddos 1K. Organized by the Park Foundation of Waukesha, the event serves as a fundraiser to enhance local parks and recreation..

The Earth Day 50K/15 Mile/5 Mile event, taking place in Crystal Lake, IL, offers runners a choice of three distances to celebrate Earth Day. The race features a scenic 5-mile loop course that includes single track and rolling hills, with a major aid station providing refreshments. Participants are e..

Childish Nonsense is a whimsical running event taking place at Deer Grove Forest Preserve in Palatine, IL. Participants can choose from various distances, including a 50 Miler, 50K, 25K, and 10K, all set on a wide, non-technical trail. The event aims to foster a sense of community and joy in ultraru..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting long-distance running event taking place in the scenic Kettle Moraine State Forest. Participants can choose from various race formats, including a 6-hour, 12-hour, 24-hour solo, and a 4-person relay. The course features three unique loops of..

The Great Western Half-Marathon & 10K, organized by the Fox River Trail Runners, is a well-established running event held on the scenic Great Western Trail. Celebrating over 25 years, this competitive race features a flat, out-and-back course, making it accessible for runners of all levels. Schedule..

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 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..

Bong Backyards is an exciting trail and ultra running event scheduled for June 6, 2025, at the Richard Bong State Recreation Area in Brighton, WI. This event caters to runners of all skill levels, offering multiple race distances, including the challenging Backyard Ultra and the shorter Backyard 24...

The Kettle Moraine 100 Endurance Races is a premier ultra marathon event held annually in June, featuring a variety of race distances including 100 miles, 100 kilometers, 50 kilometers, and 38 miles. Established in 1996, this trail race showcases the scenic beauty of the Kettle Moraine region, with..

The Whitewater Trail Challenge is an exciting running event taking place on June 21, 2025, in Whitewater, Wisconsin. Participants can choose from three race distances: a 10K, a half marathon (21K), and a 50K, all set against the stunning backdrop of the Ice Age Trail. This iconic trail spans 1,200 m..

The Kishwauketoe 5K Cross Country Run is an exciting running event taking place at the Kishwauketoe Nature Conservancy 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 h..

The Jennie Hamilton Memorial 5 Mile Trail Run is set to take place at Stoney Run County Park in Hebron, Indiana. This event is part of the Crazy Legs Race Series, which aims to promote trail running in the Northwest Indiana region. Participants can expect a challenging course with features such as m..

The Oakadoke Trail Runs is a summer trail running event held in Valparaiso, Indiana, featuring three race distances: 18 miles, 9 miles, and 4 miles. Participants will navigate scenic, tree-covered single-track trails with various elevations and terrain challenges. The event promotes inclusivity, all..

The Gristmill Grind 10K is an annual trail race held at Franklin Creek State Parks Natural Area, known for its challenging terrain and scenic views. Scheduled for August 30, 2025, this event features a 10K race with significant elevation changes and creek crossings, as well as a 1-mile walk. Partici..

The Chupacabra Endurance Run is a 10-hour race taking place at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants will tackle a loop of 4.1-4.2 miles, consisting of both pavement and single-track trails, with the challenge of completing each loop wit..

The Naperville Trails Half Marathon & 10K is a scenic running event taking place in Wheaton, IL, 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 Preserve. Thi..