Trail Running calendar near Hoffman Estates 2025-2026

The Hickory Knolls Trail Run is an annual trail running event held at the Hickory Knolls Nature Area in St. Charles, Illinois. The race offers three options: a 5K run/walk (one loop), a 10K run (two loops), and a 10K relay for two-person teams, with each member running one 5K loop.The course feature..

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 the region. The event offers three race distances: 10K, half marathon (21K), and 50..

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 Pinetum Mind Games Endurance Event, held at Lowell Park in Dixon, Illinois, is a unique endurance challenge featuring 6, 12, and 24-hour running or relay options. Participants run, walk, or crawl around a 0.411-mile loop known as the Pinetum, testing their mental toughness in a fun, supportive a..

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 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, or join a three-person relay team. The race starts just before sunset,..

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 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 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, 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..

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..

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 meadows, and 20% gravel paths, with about 6,200 feet of elevation gain..

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..