Trail Running calendar near Roseland 2026-2027

Experience a unique multi-terrain race through the scenic sand dunes and woodland trails of Western Michigan. Scale the iconic steps of Mt. Baldhead and celebrate your achievement at a festive post-race party in downtown Saugatuck.

An obstacle course race at Indiana Dunes National Park on September 13, 2026, featuring 10k, 5K and a K9 3.1-mile event. The course uses varied landscapes to reflect terrains associated with military service.

A family-oriented Rogue Obstacle Adventure Race at Sherman Lake YMCA on September 13, 2026, featuring mud pits, water, color and obstacles across one and two mile courses for ages 5 to 14.

A five hour endurance event at Franke Park where runners, mountain bikers and wheelchair athletes complete as many full laps as possible on separate loops. Food and drinks are available at a central HUB and winners are top lap counts per ca..

Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.

A timed 6 hour and 12 hour event on a 2 mile lakefront loop in Evanston that passes Northwestern University's campus. The race includes two aid stations, public fountains, handmade finisher awards, and a non alcoholic Hop Water for finisher..

Multiple trail distances run on a 4 mile loop at Tryon Farm with grassy fields, singletrack and short pavement. Proceeds benefit the Tryon Farm Institute and the event is part of the Crazy Legs Race Series.

Trail running through Fenn Valley vineyards on October 3, 2026, with a timed, challenging 5K and an untimed 1 mile course amid harvest sights and smells.

A community trail event in Valparaiso with a single-loop 5K and a two-loop 30K team relay hosted by local firefighters, featuring chip timing, aid stations, and team results.

Experience an ultra running tradition in Albion Indiana through the IGNITE Trail Series. Choose between 50, 100, or 150 mile distances on a 25 mile loop course with pacer options for the longer distances.

A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.

A community trail event on October 10, 2026 in Holland, Michigan honoring first responders and people affected by cancer. Options include a 5K Run or Walk and a 2K Walk on a scenic course that includes a hill.

Trail races at Lawless Park in Vandalia, Michigan on an all trail course through forest, streams and lakes. Distances include a half marathon, 10K, 5K and a 1K kids run with chip timing and on course aid.

A community 5K cross-country run at Portage on October 10, 2026, using the local high school course. Pre-registration includes a race t-shirt; top 50 finishers receive medals.

A timed trail event at St. Patrick's County Park in South Bend offering 24 hour, 12 hour, and 6 hour formats on mostly dirt and grass trails. Park amenities are available and proceeds benefit the ALS community.

A Halloween themed nighttime run and walk at Lake County Fairgrounds in Crown Point on October 30, 2026. The event features a 5K and a non timed shorter course, costume prizes, awards, and entry to the Hometown Hocus Pocus Market.

Bigfoot Half Trail Run at Stoney Run County Park in Hebron IN is a two-loop trail race over mixed surfaces with aid stations, packet pickup, raffle items for park fundraising and manual finishing with numbered popsicle sticks.

The St. Joe Valley Happy Trail Run will take place in Roseland from Saturday 14 November 2026 to Monday 16 November 2026. You can run between 5 and 13 miles.

A mixed-surface 5K run/walk at Homestead High School Environmental Center with a short 15,000 centimeter Turkey Toddlers trot for children 10 and under. Packet pickup is available the day before and the morning of the event.

A trail based Turkey Trot at Southwestern Michigan College offering 10K, 5K and a free 1K kids run, chip timed with live results, guaranteed tech shirts for early registrants and age division medals.