Trail Running calendar near St. Charles 2025-2026

The Frozen Tundra IPA 5K is an exciting running event taking place in Lincolnshire, Illinois. Participants can enjoy a brisk 5K run, with all runners receiving a long sleeve shirt, a finisher medal, and a $15 gift card to local establishments. The event also features a lively post-race party, comple..

ARKTOS is an ultra-running event taking place in Dousman, Wisconsin, from February 22 to 23, 2025. The event features various challenges, including 6-hour, 12-hour, and 20-hour races, available for both solo runners and relay teams of up to four participants. With a cap of 160 runners, the event is ..

The Bald Unyielding Twilight Trail Trial is an exciting ultra-running event taking place at the Bald Hill Prairie Preserve in Mount Morris, Illinois. Scheduled for February 22-23, 2025, this unique nighttime race features three timed events: a 3-hour, 6-hour, and 12-hour challenge, allowing particip..

The Yeti Trail Half Marathon is set to take place at Bluhm County Park in Westville, Indiana, on February 22, 2025. This event features a challenging course consisting of three loops primarily on single-track dirt trails, complete with switchbacks and tree roots. Participants will experience manual ..

The Foot Pursuit 5K Trail Race is a challenging 3.1-mile run/walk set in the scenic Sunset Hill County Park in Valparaiso, Indiana. Scheduled for March 1, 2025, this event features a wooded trail with rolling hills and unpredictable weather, promising an exciting experience for participants. Runners..

The Tombstone 30k/50k Trail Run is set to take place at Sunset Hill Farm County Park in Valparaiso, Indiana, on March 8, 2025. Participants can choose between two distances: a 30k and a 50k trail run, both featuring challenging loops that include the famous "Roller Coaster" hills. Runners will recei..

The Muddy Shamrock @ The Forge is an exciting trail running event taking place in Lemont, IL, featuring a Trail Half Marathon and a Trail Quarter Marathon. Scheduled for March 15, 2025, this fourth annual race promises a challenging course through scenic wooded trails, including single and double-tr..

The Skunk Ape 806/314 Trail Race is a unique running event taking place on March 22, 2025, in Dixon, Illinois. Participants can choose between two challenging distances: 33.75 miles to be completed in 8 hours and 6 minutes, or 13.5 miles in 3 hours and 14 minutes. The race features a 2.25-mile loop ..

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 on April 26, 2025, in Crystal Lake, IL, offers participants a choice of three race distances. The course features a scenic 5-mile loop through single track and rolling hills, designed to challenge runners while promoting a landfill-free environmen..

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 emphasizes community and inclusivity, offering free en..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting long-distance running event taking place in the scenic Kettle Moraine State Forest. Scheduled for May 3-4, 2025, participants can choose from various race formats, including 6-hour, 12-hour, and 24-hour solo or relay options. The course feat..

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 Yeti 7-11 Hour Endurance Run is a unique trail running event that combines endurance, camaraderie, and a fun atmosphere. Set in Willow Springs, Illinois, participants can choose between 7-hour and 11-hour races on a scenic 4-mile loop through the Palos Preserves. The course features a mi..

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 in the scenic Kettle Moraine region, featuring a variety of race distances including 100 miles, 100k, 50k, and 38 miles. Established in 1996, this trail race showcases the beautiful Ice Age Trail, with 65 miles of the cour..

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, and a 50K, all set against the stunning backdrop of the Ice Age Trail, a 1,200-mile scenic footpath. The cou..

The Kishwauketoe 5K Cross Country Run is an exciting running event taking place at the Kishwauketoe Nature Conservancy in Williams Bay, Wisconsin. The event features a 5K run/walk and a children's 1/4 mile walk/run, making it accessible for participants of all ages. The course winds through scenic g..