Trail Running calendar near Cherry Valley 2025-2026

The Whitewater Trail Challenge is a scenic trail running event held in Whitewater, Wisconsin, featuring distances of 10K, half marathon, and 50K. Set along a picturesque segment of the Ice Age Trail near Rice Lake, the course showcases rolling hills and well-established trails shaped by glacial hist..

The Kishwauketoe 5K Cross Country Run takes place in Williams Bay, Wisconsin, starting at the KNC entrance on Highway 67. The course features scenic grass trails through hills, woods, and prairie, offering a natural and challenging terrain for runners. The event includes a 5K run/walk and a children..

The Pinetum Mind Games Endurance Event, held at Lowell Park in Dixon, Illinois, is a unique running challenge featuring a 0.411-mile loop course through the pine tree upper loop area. Participants can choose from 6, 12, or 24-hour solo runs or three-person relays, starting on a Friday evening. The e..

The Chupacabra Trail Races take place in Dixon, Illinois, featuring night trail running on a 5-mile loop course composed of grass, gravel, dirt, and 30% single track. Participants can choose from distances of 5, 10, or 15 miles by completing one to three laps, or join a three-person relay team. The..

The New Glarus Woods Trail Run is an annual event held at New Glarus Woods State Park in Wisconsin, part of the Savanna Trail Run Series. The 6th edition features multiple race distances: a 1-mile kids' fun run, 5 km, 8 km, and 16 km trail runs. The event supports the development of mountain bike tr..

Run The Hawk Trail Run takes place at the historic Blackhawk Ski Club in Middleton, Wisconsin. This endurance event features 3, 6, and 12-hour challenges where participants complete as many laps as possible on a scenic 2.25-mile loop with 345 feet of elevation gain per lap. The course includes diver..

The Summer Trail Classic is a trail running event held at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. It offers three race distances: approximately 4 miles, 9.5 miles, and 13 miles, featuring twisting single-track trails that provide a true trail running experience. The event is part..

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 hill climbs, and four creek cr..

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, set for September 6, 2025. Participants can choose between a USATF-certified half marathon or 10K race, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on crushe..

The Hobo Trail Runs, hosted by Rockford Road Runners, take place at Rock Cut State Park in Rockford, Illinois. This annual event offers multiple trail running distances including 10k, 25k, and 50k races, with options to participate in single races or the challenging Triple Crown series (85k total) o..

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 ultrarunning fare and additional vendor treats like ho..

Last Dot Standing is a unique endurance running event held at Belleville Community Park in Belleville, Wisconsin. Participants alternate running 4.2-mile legs between Belleville and Dot's Tavern, a historic local tavern, with one hour to complete each segment. The race continues hourly until only on..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. This 10-mile course features twists, turns, and hills, offering a challenging and scenic run through natural settings. Participants receive a custom finisher's medal, shirt, and..

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..

Hindsight Ultra Trail Runs, held in Dixon, Illinois, offers a grassroots ultra running experience with distances of 25K, 50K, 100K, and 100 miles. The course features a 7.85-mile loop combining roughly 50% singletrack, 30% grassy meadow paths, and 20% gravel, with about 6,200 feet of elevation gain..

The Hennepin Hundred is a premier ultramarathon held in Sterling, Illinois, featuring 100-mile, 50-mile, 50K, and 100-mile team relay races. The point-to-point course follows the scenic, flat, and fast Hennepin Canal State Trail, Illinois’ longest multi-use trail, stretching from Sterling to Colona..

The Trail Run at Indian Lake is an exciting running event held at Indian Lake County Park, featuring two course options: a long course of approximately 10.5 km and a short course of about 5.8 km. The event promotes sustainability by adopting a cup-free policy, encouraging participants to bring their..

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..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

Zachariah's Acres Fall Run, Walk & Roll is a scenic event held in Oconomowoc, Wisconsin, featuring a 5K, half marathon, and a family-friendly 1-mile walk/roll. Set on 125 acres of natural beauty, the course includes tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The fa..