Experience a truly unique and historic five-mile journey at the Fort2Fort Five Mile Challenge, held on Mackinac Island, Michigan, on Saturday, May 9, 2026. This challenging yet rewarding race kicks off with the thrilling sound of a musket firing inside Fort Mackinac, sending runners and walkers through the iconic Sally Port gate to begin their adventure. The course is anything but flat, taking participants on beautiful paved trails that wind past breathtaking island landmarks, including the stunning Arch Rock, the historic cemeteries, Sugarloaf Rock, and Point Lookout. The ultimate test of endurance is the ascent to Fort Holmes, the highest point on the island, offering panoramic views of the Straits. This scenic and historic route then leads participants back down to finish on the lawn behind Fort Mackinac.

Now in its ninth year, the Fort2Fort Five Mile Challenge has established itself as a must-do event, renowned for its captivating scenery and its significant contribution to the Mackinac Historic State Parks. Runners can expect aid stations and restrooms conveniently located along the course, with additional facilities available inside Fort Mackinac and at the Huron Road Pavilion near the start/finish area. Upon completing this memorable race, every participant receives a commemorative race shirt, a unique "woodalion" finisher medal, and free entry to Fort Mackinac and other state historic parks for the entire day, making it an exceptional experience beyond the run itself. After crossing the finish line, join fellow participants for an awards ceremony hosted by The Pink Pony, complete with light appetizers. Typical race day conditions in early May feature pleasant highs around 60°F and lows around 37°F, with only a 12% chance of precipitation, providing ideal weather for tackling the challenging yet incredibly picturesque course.