Trail Running calendar near Roseland 2025-2026

The Chupacabra Endurance 10-hour Run is held at Bluhm County Park in Westville, Indiana. This challenging event features a 3.4-3.5 mile trail loop with minimal pavement, which runners must complete within one hour per loop or face elimination. The race lasts 10 hours, testing endurance and speed, wi..

The Farm Fresh 5k and 1 mile at Gast Family Farms takes place in Saint Joseph, Michigan (5165 Lincoln Avenue). The event offers two distances—a 5k trail run and a 1-mile option—through farm fields on an informal, made-up route that can twist and turn depending on harvest activity. Runners and walker..

Mt. Baldhead Challenge in Saugatuck, Michigan, is the Midwest’s premier multi-terrain race. Participants choose the 10K+ (about 7 miles) or the Half Marathon (13.1 miles), weaving through woodlands, dunes, waterfront views, and the friendly streets of Saugatuck–Douglas to the Mt.Baldhead summit. The..

Firefly Six Hour Trail Race is a six-hour timed night trail race at Franke Park in Fort Wayne, Indiana. Runners complete as many laps as they can on a 4.1-mile loop featuring about one mile of paved path, two miles of gravel, and one mile of single-track dirt. Each loop starts and finishes at the HU..

DIRTY FOX FIVE HOUR TRAIL RELAY is a five-hour trail race at Franke Park in Fort Wayne, Indiana. Runners follow a three-mile loop on the east side, while riders tackle a five-mile loop on the west. Teams or solo participants aim to complete as many full laps as possible within the time limit, with n..

Timely Nonsense is an urban ultramarathon held at a 58-acre park in Chicago, at the intersection of California and Montrose. The course features a 0.75-mile paved loop that runners complete for the 6-hour or 12-hour timed events. An aid station at the Start/Finish provides typical ultrarunning fare,..

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 Tryon Farm 50k is a trail running event held at Tryon Farm in Michigan City, Indiana. The course features an 8-loop 4-mile trail combining open grassy fields, single-track dirt trails, and small pavement sections. The event also offers shorter distances including 2-mile, 4-mile, 8-mile, and 25k..

The Gwi-Zhetomen Ode 5K and 1 Mile Trail Challenge is an annual running event held at Camp Jijak in Hopkins, Michigan. It features a 5K run/walk and a 1-mile trail challenge, welcoming participants of all ages with various age group categories. The event also includes a unique "24 Miles in 24 Hours"..

Bloomingdale Trail 5K is an annual, family-friendly running event in Chicago, Illinois. The day features a timed 5K race along with ¼- and ½-mile dashes for young runners. The event location is 1834 N Lawndale Ave, Chicago, IL 60647, and the site describes a welcoming atmosphere for runners of all a..

The Fenn Valley Vine Wine'd is an annual running event held at Fenn Valley Vineyards and Wine Cellar in Fennville, Michigan. Celebrating its 13th year in 2025, the race offers a scenic 5K trail run and a 1-mile untimed course through premium wine grape vineyards, meadows, and diverse forested ecosys..

Glory Days 5K Community Run at The Portage Invitational takes place in Portage, Michigan, on Moorsbridge Rd. The 5K course offers participants a chance to run a real cross-country route that has been used by thousands of student athletes. The event is open to the entire community, including spectato..

Indiana Trail 100 is an Ignite Trail Series ultramarathon held at Chain O’Lakes State Park in Albion, Indiana, on October 11–12, 2025. The event offers 100-mile, 75-mile, and 50-mile race distances run on a multi-loop trail course. It serves as a Western States qualifier and is renowned for its enth..

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..

NIJC Community for Immigrant Justice 5K is a 5K run/walk organized by the National Immigrant Justice Center. It offers in-person participation on race day at Millrace Trail in Goshen, Indiana, or a virtual option through the race week. Participants can run a 5K on the Millrace Trail course or on the..

St. Pats 24 Hour Race is a timed trail event held at St. Patrick’s County Park in South Bend, Indiana.It offers 12- and 24-hour options on scenic dirt and grass trails, with three short asphalt segments mixed into the loop. Runners may extend their efforts with a final 0.25-mile out-and-back during..

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..

Witches in the Woods 5K/2K is a Halloween-themed running event at the Lake County Fairgrounds in Crown Point, Indiana. Participants can choose a 5K Timed Halloween Run or a Non-Timed Halloween 2K Walk. The night-time course weaves through the fairgrounds’ trees and surrounding roads, with flashlight..

Bigfoot Half Trail Run takes place at Stoney Run County Park in Hebron, Indiana. The course covers the half marathon distance by circulating the park twice on trail terrain. Runners will have two aid stations: one at the start/finish area and an unmanned aid station around mile 3.5.All runners recei..

The St. Joe Valley Happy Trail Run takes place at St. Patrick's County Park in South Bend, Indiana.This event offers multiple distances including a 1-mile fun run, 5k, 10k, and a half marathon, all on beginner-friendly trails with beautiful scenery. The course features loops: 5k is one loop, 10k two..