Trail Running calendar near Roseland 2026-2027

Trail half marathon, 10K and ruck events at Riley Trails in Holland MI with proceeds supporting the Egress Endurance Project.

A 5K chip-timed run and a 3K scavenger-hunt walk through St. Patrick's County Park featuring trail terrain, participant medallions, post-event refreshments, awards by age group, and proceeds that support park programs.

Alumni cross country meet in Chicago Heights on August 15 2026 using the old 2 Miles course with decade-based teams, chip timing and place-based scoring.

A chip timed 5K trail run at Salamonie Lake with wooded, gently rolling trails, a participant pancake breakfast, and fresh sweet corn for sale. Proceeds support Friends of the Upper Wabash Interpretive Services.

A 10 hour trail endurance event at Bluhm County Park on August 29, 2026 with hourly loop cutoffs, chip based prizes, and a race t shirt and wooden medal.

A 6 km cross-country race at Lovelace Park in Evanston with scholastic races, team and individual entries, race shirts, awards, and a post-race gathering with food.

A six hour timed night trail event at Franke Park where participants complete laps on paved, gravel and single track trails with laps recorded on a whiteboard and electronically.

A casual farm-based fun run on September 5, 2026 at Gast Family Farms offering a 5K and 1 Mile through farm fields; $10 registration supports the Lakeshore Lions and includes a shirt, medal, and grape juice.

A remembrance event at the Lake County Fairgrounds Grandstand in Crown Pont, IN where participants climb 17 laps totaling 1,980 steps or join a 1 mile non timed walk. The event includes hero wristbands, limited finisher medals, and supports..

A timed urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.

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.

A one day trail running festival in Beecher, IL offering natural-terrain distances from 3 to 31 miles, cupless aid stations, finisher shirts and medals, a ruck category with weight rules, and awards including a DFL prize for the 50K.

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 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..

Conquer 14000 steps at Waldo Stadium to earn 14ER status in this unique stair climbing challenge. Participate as an individual or form a relay team of two to four people to complete the trek within three hours.

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.

Timed 6 and 12 hour events on a 2 mile lakefront loop in Evanston with two aid stations, public water fountains, nearby parking, and a nonalcoholic finish beverage and finisher award.

Trail runs and a fun run/walk on a 4-mile loop at Tryon Farm, with multiple distance options and aid at the main station.

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.

Trail races at Creekside Trails in Valparaiso on October 3, 2026: a 5K loop and a 30K team relay hosted by local firefighters.