Trail Running calendar near Oconomowoc 2025-2026

DWD Devil's Lake is a trail running event held in Baraboo, Wisconsin, just north of Madison, set against the stunning geological backdrop of Devil's Lake, shaped by the Ice Age. The race offers multiple distances including 10K, half marathon (13.1 miles), marathon (26.2 miles), 50K, and 50 miles, ca..

The Byron Fest 5K & 1 Mile Fun Run is an annual family-friendly event held at the scenic Byron Forest Preserve in Byron, Illinois. The 5K race features well-maintained trails with panoramic views and varied terrain, making it part of the 2024 Rockford Road Runners Circuit Race. Chip timing is provid..

The Cliff Runner 10K is an extreme trail running event held in Sherwood, Wisconsin, within High Cliff State Park. Covering a challenging 10-kilometer course, the race features mostly single-track trails with natural obstacles such as rocks, roots, boulders, and hills, accumulating over 500 feet of e..

The Thanks Sandy event is a 9-mile trail run held at Kohler-Andrae State Park in Sheboygan, Wisconsin. The course features a mostly flat terrain with a total elevation gain of 509 feet and descent of 485 feet, combining concrete paths, wide trails, sandy shoreline running along Lake Michigan, marsh,..

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 offers 3, 6, and 12-hour solo and relay challenges on a scenic 2.25-mile loop course featuring 345 feet of elevation gain per lap. Runners experience diverse terrain including grass pa..

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 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 free community running event held in Crystal Lake, Illinois, celebrating local trail running and races. Organized by UltraSignup, this one-day festival features a social group run with options of 3 or 5 miles through scenic Veteran Acres Park. The event fosters camaraderie..

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 Fallinline 125 is an ultramarathon event held in Greenbush, Wisconsin, covering approximately 132 miles through the scenic Kettle Moraine State Forest along the Ice Age National Scenic Trail. The course traverses the Northern, Middle, and Southern Kettle units, featuring a mix of rugged single-t..

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..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually in Waukesha, Wisconsin, at Fox River Park. This race honors the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast from Heritage Christian School. The course features a scenic trail through the woods, o..

Twisted Roots is a trail running event held at High Cliff State Park in Sherwood, Wisconsin, featuring both half marathon and full marathon distances. Set against the scenic backdrop of Lake Winnebago and the Niagara Escarpment's majestic cliffs, runners experience a mix of technical single tracks a..

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..

The S'more Fun Trail Run takes place at Mirror Lake State Park in Baraboo, Wisconsin, offering a variety of distances including a Mini-Marshmallow Mile for kids 11 and under, 5K trail walk and run, 10K trail run, and a half marathon trail run. Participants experience scenic trails featuring Mirror L..

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..

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..