Trail Running calendar near Bristol 2025-2026

Summer Trail Classic takes place on August 24, 2025 at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. The event offers three trail distances: approximately 4 miles, 9.5 miles, and 13 miles, forming the third stop in the Dick Pond Athletics Darn Tough Trail Race Series. Runners navigate t..

Naperville Trails Half Marathon & 10K, hosted by All Community Events, takes place in the Danada Forest Preserve area near Wheaton/Naperville, Illinois. It offers two distances: a USATF-certified half marathon and a 10K along crushed limestone trails, finishing around a grassy horse-racing track. Th..

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..

Dirt Circus Chicago is a one-day, free community trail-running festival in the Chicago area, organized by UltraSignup. The event blends a casual social run with a pop-up expo featuring local race directors, brands, shops, and coaches. Participants choose between two routes, approximately 4.5 miles o..

Timely Nonsense is an urban ultramarathon held at a 58-acre park in Chicago, at the intersection of California and Montrose. The course features a 0.75-mile paved loop that runners complete for the 6-hour or 12-hour timed events. An aid station at the Start/Finish provides typical ultrarunning fare,..

Last Dot Standing at Belleville, Wisconsin, organized by Ten Junk Miles Racing, kicks off at Belleville Community Park. The LMS format features a 4.2-mile out-and-back course between Belleville and Dot's Tavern, a 70-year-old tavern off the trail; each leg must be completed in one hour, with the nex..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. The 8th edition of this event features a challenging 10-mile course with twists, turns, and hills through scenic natural areas. Participants receive a custom finisher's medal and..

Half Day at the Lake is a unique ultra-running event held in Evanston, Illinois, featuring 6- and 12-hour race options. The race takes place on a scenic 2-mile loop along Chicago’s north shore lakefront path, passing through Evanston’s lakefront and Northwestern University’s campus. The course is a..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually at Fox River Park in Waukesha, Wisconsin, honoring the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast. The race features a scenic trail course through the woods, offering a refreshing alternative to..

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..

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 races on wide, well-groomed ski and hiking trails. The 5K course tours the park's middle level, while the 10K f..

Zachariah's Acres Fall Run, Walk & Roll is held in Oconomowoc, Wisconsin, on a scenic 125-acre private property featuring tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The event offers a 5K, a half marathon, and a family-friendly 1-mile walk/roll loop with gentle hill..

The Des Plaines River Trail Races, held in Lake County, Illinois, offer a scenic and fast trail running experience with distances including a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Starting and finishing at Half Day Forest Preserve, the course features a flat, wide, crus..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event includes three distances: a 5-mile run, a 5-mile bike, and a final 5-mile run, with options for solo competition or 2- or 3-person relays (Soulo, or teams). The run takes place on wide, gro..

Race For Open Space is a West Bend, Wisconsin trail running event at Cedar Lakes Conservation Foundation's Fox Hill Nature Preserve. It offers a 5K trail run, a 10K trail run (two loops), a 1-mile trail walk, and a 5K for ages 18 & under. The course traverses deciduous forest, restored prairieland,..

Soul Crusher is a trail-running event in Crystal Lake, Illinois, offering 5- and 10-mile options. Runners navigate single-track forest trails through Veteran Acres and Sternes Woods, with a course described as challenging, fun, and bone-decorated. The start line sits in the middle of the park at a s..

Palos Park Spooky Shuffle 2025 is a 5K and 10K trail run/walk held at Swallow Cliff South Forest Preserve in Palos Park, IL, organized by the Palos Park Department of Recreation & Parks in partnership with the Forest Preserves of Cook County. Runners traverse the Sag Valley Trail System on wide, unp..

The Over The Vines Wine Run/Walk is held at Over the Vines Vineyard & Wine Barn in Edgerton, Wisconsin. This event offers a 5K timed run, a 5K untimed walk, and a 2K untimed walk, all on a scenic trail featuring grass, gravel, and compacted dirt terrain. Participants must be 21 or older and enjoy fo..

Fancy Nonsense 25k/50k is a whimsical ultramarathon organized by CUSS Running, held near Chicago at Red Gate Woods in the Palos Trail System (Willow Springs/Lemont, IL). The course is a 5.5-mile mostly runnable single-track loop, repeated to reach 25k or 50k. Expect a playful, mischievous atmosphere..

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and picturesque experience amid vibrant fall colors. Both races..