Trail Running calendar near Waukesha 2024-2025

The Frigid Fox Ultra Trek will take place in New Prospect on Saturday 11 January 2025.

The Frozen Gnome is a challenging winter running event held in Crystal Lake, IL, featuring a scenic course through Veteran Acres and Sterne’s Woods. Participants can choose between a 50K ultra run or a 10K race, both rated as "Triple Black Diamond" for their difficulty. The 50K consists of five loop..

The 50K Mashup Slam is a series of challenging 50K trail races held throughout the Midwest, designed to celebrate the often-overlooked distance in ultrarunning. Kicking off in January with the Frozen Gnome 50K and concluding in November with the Miner 49er 50K, participants who complete all five rac..

The Frozen Assets 5K Run/Walk, organized by Clean Lakes Alliance, invites participants to experience a unique running event on the frozen surface of Lake Mendota in Madison, Wisconsin. This event features both a chip-timed 5K and an untimed walking option, allowing participants of all skill levels t..

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

The NK50k is an annual trail running event held in Greenbush, Wisconsin, featuring a scenic point-to-point course along the Northern Kettle Moraine Ice Age Trail. Participants can expect a fun and challenging experience, with aid stations providing water, sports drinks, and snacks throughout the rou..

The Trailbreaker is a running event scheduled for April 6, 2025, in Waukesha, Wisconsin. It features a variety of race options, including a marathon along the scenic Glacial Drumlin Trail, a half marathon, 10K, 5K, a walking event, and a Kiddos 1K for children. This event not only promotes fitness a..

The Earth Day 50K/15 Mile/5 Mile event, taking place in Crystal Lake, IL, offers participants a choice of three race distances. The course features a scenic 5-mile loop through rolling hills and single-track trails, designed to challenge runners while promoting an eco-friendly atmosphere. The event ..

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 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 Sugar Badger 50/50 and Half is a scenic running event taking place in Belleville, Wisconsin, featuring a 50-mile, 50K, and half marathon distance. The race is set on the flat and soft rail trails of the Badger State Trail and the Sugar River State Trail, offering participants beautiful views, tr..

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 Dawn to Dusk Endurance Run is an exciting running event scheduled for June 28-29, 2025, at Camp Sinawa in Valders, WI. Participants can choose from various race durations, including 24 hours, 15.5 hours, 8 hours, 6 hours, and a unique Dusk to Dawn challenge. The course features a scenic 4.5-mile..

The Naperville Trails Half Marathon and 10K is an annual running event held in Wheaton, Illinois, featuring a scenic course through the Danada Forest Preserve. Participants can choose between a half marathon or a new 10K distance, both of which are USATF certified. The event celebrates its 15th anni..

Timely Nonsense is a unique running event taking place in Chicago, IL, featuring both 6-hour and 12-hour timed races. Participants can choose to run individually or as part of a relay team, with options for 2 or 4-person teams. The race is set in a scenic 58-acre park, where runners will navigate a ..

The Last Dot Standing event, hosted by Ten Junk Miles, takes place from September 19 to 22, 2025, in Belleville, WI. This unique running challenge requires participants to alternate between running 4.2 miles to Dot's Tavern and back, with a one-hour time limit for each leg. The event continues until..

Fallinline 125 is an exciting running event taking place in Greenbush, Wisconsin, featuring a challenging 132-mile race and a fun "Party Next Door" option. This event invites runners of all levels to participate in a unique experience that combines endurance and community spirit. Participants can re..

The Des Plaines River Trail Races feature a variety of endurance events, including a Half Marathon, Marathon, 50K, and 50 Mile race, all set along the scenic Des Plaines River Trail in Lake County, Illinois. Participants will enjoy a flat, wide, crushed gravel trail that meanders through lush forest..