Trail Running calendar near Michigan City 2025-2026

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

Run the DINO 7K Trail Run on June 20, 2026 at Potato Creek State Park for a scenic 7 km lollipop loop with two rolling hills. Part of the DINO Trail Run Series, the event awards series points and age group medals.

Take on the Trail Golf Endurance Challenge in Valparaiso on June 27, 2026 at Trailyard Outpost. Choose 50K, 10 mile or relay teams and tackle looped timed holes with rolling climbs and golf style scoring that blends pace and strategy.

Tackle tree covered single track and creek crossings at Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 18 mile, 9 mile, and 4 mile options for all abilities. Custom finisher awards and youth pricing make this a fun family friendl..

Run the Mattawan Wildcat Road and Trail 5K through neighborhood streets and scenic wooded trails, finishing on school grounds with a festive community vibe. All finishers earn medals and proceeds support Brainstrong education programs.

Take on the Mt Baldhead Challenge in Saugatuck, Michigan with a 10K plus or half marathon course that winds through trails, dunes and downtown streets. Both routes include the iconic 302 step climb and finish in Coghlin Park.

Experience scenic 4 mile loops across grassy fields and single track trails at Tryon Farm, with distances from a 2 mile fun run to a 50k ultra. Proceeds support Tryon Farm Institute and the race is part of the Crazy Legs series.

Fancy Nonsense is a looped trail race at Red Gate Woods near Willow Springs and Lemont, Illinois, with 50K, 25K and 5 mile options on runnable singletrack. Expect repeated 5.5 mile loops, plentiful aid and classic ultra snacks.

Join the Bigfoot Half Trail Run on November 14, 2026 at Stoney Run County Park in Hebron, IN for a scenic two-loop course across fields, trails and gravel. Enjoy on-course aid, raffle prizes and event merch in a friendly, relaxed race atmos..

The Forge Trail Run Festival in Lemont Illinois offers 10K to 60K on scenic single and double track trails around the quarries and the I&M Canal. Field capped at 400 with lap courses that call for trail shoes and self supported hydration.