Trail Running calendar near Whitewater 2025-2026

Located in Franklin Grove, Illinois, the Grist Mill Grind 10K is a technical trail race held in Franklin Creek State Park’s natural area. The fifth annual event offers a challenging 10K course with about 800 feet of elevation gain, winding over forest trails with several hills and four crossings of..

Badgerland Striders 24-12-6 Hour Runs takes place at Lapham Peak State Park in Delafield, Wisconsin. Runners choose 24-, 12-, or 6-hour formats, with day or night divisions for the shorter races, plus a Distance division for longer goals (marathon, 50K, 50 miles). The course is a 1-mile loop on a ge..

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..

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..

Fallinline 125 is a two-day ultramarathon in Greenbush, Wisconsin, run through the Kettle Moraine State Forest along the Ice Age National Scenic Trail. Limited to 75 entrants, the main 132-mile event features aid stations and a 48-hour, 46-minute time limit, offering a grueling, scenic challenge acr..

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..

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..

Queen of the Ridge is a women-only endurance running event held on a family dairy farm in Arena, Wisconsin, located in the scenic Driftless Area near Madison. This unique race features a "Last Woman Standing" format where female runners complete a challenging 1 to 1.25-mile loop with at least 250 fe..

Anderson Humane's Walk4Animals & 5K Run takes place in Batavia, Illinois, centered at the Peg Bond Center at 100 N Island Ave along the Batavia Riverwalk. The event offers a 5K Run (timed), a 1.5-mile Walk, and a T-Shirt Only option. The Walk4Animals route is a 1.65-mile loop around the Batavia Rive..

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. The course features scenic views along Mirror Lake, sand..

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..

The Trail Run at Indian Lake is a scenic trail running event held at Indian Lake County Park in Cross Plains, Wisconsin. The race offers two distances: a long course of approximately 10.5 km and a short course of about 5.8 km. The course begins in a restored sedge meadow near the kettle lake formed..

Autumn Leaf Run is a 5K trail race held in Freeport, Illinois, at Oakdale Nature Preserve. The course loops through diverse terrain, including wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and several single-track sections. The start and finish are in close proximity, and..

The Milwaukee Beer Run 5k & .05k takes place in Glendale, Wisconsin, at the Bavarian Bierhaus. The event features a 5k Beer Run/Walk (3.1 miles) and a 54-yard .05k Beer Run/Walk, with a virtual option for remote participants. The course is an out-and-back run along the tree-lined Oak Leaf Trail, fin..

Farmer Ken's Pumpkin Dash 5K takes place in Franksville, Wisconsin (53126). It is a 5K trail run along a grass/dirt path set beside corn and other farm fields, offering a scenic rural landscape. The course runs through agricultural surroundings, giving runners a scenic, rustic experience.Participant..

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..