Trail Running calendar near Portage 2025-2026

The Oakadoke Trail Runs, held in Valparaiso, Indiana, is a summer trail running event featuring challenging courses through the scenic Creekside Trails. Participants can choose from three distances: 18 miles (two loops), 9 miles (one full loop), and 4 miles (half loop focusing on the Salt Creek sect..

Run the Rails is a community running event held in Elburn, Illinois, featuring a 4-mile run, a 7-mile run, and a 1-mile fun run. Presented by the Elburn Parks Commission, the race offers a vibrant atmosphere with opportunities for local businesses to sponsor and gain visibility through banners, race..

The Running Wild 5K Run & 3K Scavenger Hunt Walk takes place at St. Patrick's County Park in South Bend, Indiana. The 5K run is professionally chip-timed and features a course through wooded and open field trails, park roads, grass, and gravel, with awards for top finishers in various age categories..

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, providing a true trail running experience on twisting single-track trails. The event is part of the 202..

The Chupacabra Endurance Run is a 10-hour endurance race held at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants run multiple loops of a 3.4-3.5 mile trail with minimal pavement, completing each loop within one hour to avoid elimination. The event..

The Farm Fresh 5k and 1 Mile at Gast Family Farms is a fun trail run held annually at 5165 Lincoln Avenue, Saint Joseph, Michigan. Originating from a family grape juice weekend, the event has grown into a public race featuring a 5k and a 1-mile course through farm fields with a route decided just da..

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, set for September 6, 2025. Participants can choose between a USATF-certified half marathon or 10K distance, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on cr..

Dirt Circus - Chicago is a free community running event held in Crystal Lake, Illinois, celebrating local trail running culture. Organized by UltraSignup, the event features a festive atmosphere with a social run, food, raffle prizes, and an expo showcasing local races, run clubs, brands, and busine..

The Timely Nonsense - Chicago, IL will take place in Chicago on Sunday 14 September 2025.

Half Day at the Lake is a unique 6- or 12-hour ultra-running event held in Evanston, Illinois, along a scenic 2-mile loop featuring the lakefront and Northwestern University campus. The course combines paved paths and crushed gravel, offering beautiful views of the Chicago skyline. Runners share the..

The Tryon Farm 50k is a trail running event held at Tryon Farm in Michigan City, Indiana. The course features an 8-loop 4-mile circuit through a mix of open grassy fields, single-track dirt trails, and small pavement sections connecting different trail areas. The event also offers shorter distances..

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..

The Sandhill Crane All Trail Half Marathon is an annual running event held at Dr. T. K.Lawless County Park in Vandalia, Michigan. The 17th edition, scheduled for October 11, 2025, features a scenic, non-repetitive all-trail course through 820 acres of forest and fields, including six bridge crossing..

The St. Pats 24 Hour Race, held at St. Patrick's County Park in South Bend, Indiana, is a premier timed trail running event featuring 12- and 24-hour race options.Participants run primarily on scenic dirt and grass trails with brief asphalt crossings, enjoying a loop course that includes a final 0.2..

The Buckley 5 Miler is a scenic and challenging cross-country trail race held at the Buckley Homestead in Lowell, Indiana. The 5-mile course features a 2-mile loop on the north side of the park followed by a 3-mile loop through the park, finishing at the pioneer farm. Runners encounter a picturesque..

The Palos Park Spooky Shuffle is a 5K and 10K trail run/walk held at Swallow Cliff South Forest Preserve in Palos Park, Illinois. The event features scenic courses through the Sag Valley Trail System, known for its unique topography with ravines and hills uncommon in the Chicagoland area. The 5K cou..

The Witches in the Woods 5K/2K is a Halloween-themed nighttime running and walking event held at the Lake County Fairgrounds in Crown Point, Indiana. Participants can choose between a timed 5K run or a non-timed 2K walk through wooded trails and roads, so bringing flashlights or headlamps is recomme..

The Fancy Nonsense 25K/50K is a whimsical ultramarathon held in the Palos Trail System near Willow Springs and Lemont, Illinois, about 20 minutes from downtown Chicago. Runners can choose from 25K, 50K, or 5-mile distances on a mostly single-track, 5.5-mile loop course that encourages joy and imagin..

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..

The Big Timber XC Challenge is a trail running event held at Camp Big Timber in Elgin, Illinois. Participants can choose between a 3-mile run/walk (one loop) or a 5-mile run (two loops) through a natural wooded area featuring grass, gravel, dirt, and a notable creek crossing with a rope for support...