Trail Running calendar near Freeport 2025-2026

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..

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..

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 Swiss Valley Trail Races, held in Peosta, Iowa, offer runners three distance options: 5.2 miles, 25K, and 50K. Set within the scenic Swiss Valley Nature Preserve, the course features rugged terrain, creek crossings, and steep inclines, with each 5.2-mile loop climbing approximately 875 feet. The..

October 4-5, 2025, The Hennepin Hundred is Illinois’ only point-to-point, all-trail ultramarathon, running from Sterling along the Rock River to Colona near the Mississippi and following the 104-mile Hennepin Canal State Trail through northwest Illinois’ historic locks, lift bridges, and scenic farm..

The Haunted Heritage Trail Fun Run / Hero Walk in Dyersville, Iowa, offers a festive and spooky running experience with multiple events including a 5K Haunted Heritage Trail Fun Run, a 10K Trail Run, and a 1 Mile Hero Walk. Participants are encouraged to wear Halloween costumes as they navigate a 3...

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..

Mines of Spain 100, held in Dubuque, Iowa, offers 100-mile and 100-kilometer ultramarathons on October 17-18, 2025. Set in the driftless region’s bluffs, prairies and forests above the Mississippi River valley, it delivers a true Midwest trail experience. The course is described as a ~20‑mile loop f..

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..

Saw Wee Kee - Fall Trail Run is held at Saw Wee Kee Park, Sundown Lane, Yorkville, Illinois. The event is the Fall Trail Run segment of a four-race series; each race features a different course and medal piece, and completing all four earns the series medal with different seasonal swag at each stop...

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..

Black Hawk Ridge Trail Run is a trail-running event held in Mazomanie, Wisconsin, at the Black Hawk Unit of the Lower Wisconsin State Riverway. The race offers two distances, 8K and 16K, inviting runners of varied experience to tackle woodland and river-adjacent trails. Described as a scenic and his..

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..