The Whistlestop Marathon, set for October 10, 2026, in Ashland, Wisconsin, offers a truly distinctive autumn running experience with distances including a full 26.2M marathon, 13.1M half-marathon, 10K, and 5K. Renowned as the "Upper Midwest's best fall classic," this event traces the historic Tri-County Corridor, a converted rail-trail that showcases the breathtaking peak fall colors of northern Wisconsin. The USATF-certified, point-to-point course is largely a gentle, net-downhill profile, making it an excellent opportunity for personal records and a Boston Marathon qualifying race. Typical race day conditions in October feature ideal running temperatures, with highs around 57°F and lows around 36°F, and only a 12% chance of precipitation, providing a crisp and comfortable atmosphere.

Runners on the Whistlestop course will navigate a crushed limestone gravel surface, designed to be easier on the joints than asphalt, though some areas may present softer or "washboard" conditions. The scenic journey from Iron River to Ashland on Lake Superior's south shore unfolds through vibrant deciduous forests, over re-decked railroad trestles, past serene wetlands, trout streams, and through the Chequamegon National Forest, offering a traffic-free and quiet immersion in nature. While the course provides ample natural beauty, some stretches through the woods can be less populated by spectators. However, the race makes up for this with exceptional community engagement; enthusiastic local volunteers staff 15 aid stations, offering water and Powerade, with some providing food. Themed aid stations, live music at both the start and finish, and a lively post-race Blues & Brews Festival at the Bay Area Civic Center in Ashland contribute to a celebratory atmosphere.

The Whistlestop Marathon stands out not just for its picturesque course and potential for fast times, but for its deep-rooted community spirit. First established in 1997, the event has grown into a beloved tradition, attracting runners seeking a supportive environment and warm hospitality from the residents of Ashland. Shuttles are efficiently organized to transport runners to the various start lines, with the full marathon beginning east of Iron River and all distances converging on the finish line at Ashland's Railyard Park. Whether you're chasing a Boston Qualifier, aiming for a personal best, or simply looking to experience a truly beautiful and well-organized race, the Whistlestop Marathon promises a memorable fall classic.