Trail Running calendar near Richmond Township 2025-2026

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..

Elver Park Trail Run takes place at Elver Park in Madison, Wisconsin. It offers three distances: a 10K, a 5K Run/Walk, and a free 1K Kids Fun Run. All races start and finish behind the Main Shelter.The 5K uses the West Side first before returning, while the 10K continues to the East Side for a secon..

Bristol Woods Trail Run takes place in Bristol, Wisconsin at Bristol Woods County Park, hosted at the Pringle Nature Center (9800 160th Ave). The event offers a 5K Trail Run and a 2 Mile Walk, plus junior versions for participants 18 and under. The course runs along the park’s trails, described as a..

The Fast Track Cross Country Open is a 3.05-mile race held in Schaumburg, Illinois, on the MacNider cross country course near Hoover Elementary School. Scheduled for November 9, 2025, it features separate women's and men's races open to all ages and abilities. The course consists of a short start fo..

Big Timber XC Challenge is an autumn trail race held at Camp Big Timber in Elgin, Illinois (Big Timber Road at Tyrrell Road). Runners can choose between a 3-mile Run/Walk (one loop) and a 5-mile Run (two loops), with the course featuring gravel roads, open grass, wooded paths, and a creek crossing w..

The Forge Trail Run Festival takes place at The Forge: Lemont Quarries in Lemont, Illinois, a late‑fall Midwest trail event set among woods, gravel paths, and the historic Lemont Quarries and I&M Canal. Runners may choose from 10K, 20K (Half Marathon), 30K, or 60K distances. All races share a common..

The Bucks & Does 13.1 Pointer is a trail running event held in Nashotah Park, Wisconsin, featuring distances of 5K, 10K, and a half marathon (13.1 miles). The course is primarily wood-chipped with some grassy sections, shaded by trees for a comfortable run, and is run in a counterclockwise direction..

Fast Eddie 50k/5k takes place at Lapham Peak in Delafield, Wisconsin. The event offers a challenging 50K consisting of five loops on the Blue Loop, featuring rolling terrain and woodland scenery, alongside a 5K out-and-back on the same trails. Now in its inaugural 50K and fourth year for the 5K, the..

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or teams of 2 to 4 in relay format. Participants navigate chall..

Orland Park Turkey Trot is a 2.5-mile chip-timed cross-country race in Orland Park, Illinois. The annual Thanksgiving morning event invites runners and walkers to traverse paved roads, paths, and wooded sections near the Village Hall, starting at the Franklin Loebe Center (14650 S Ravinia Ave). It h..

The Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove, covering a mostly flat, crushed gravel path. Participants h..

The Frozen Gnome is a challenging winter trail running event held in Crystal Lake, Illinois, at Veteran Acres park. Featuring a "Triple Black Diamond" rated course, the race offers a 50K ultra run and a 10K race, both run on a scenic 10K single-track loop through Veteran Acres and Sterne’s Woods. Th..

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second loop to the Scuppernong Trails and back, totaling 100 kilom..