The WhistleStop Race in Ashland, Wisconsin is an annual fall trail race that began in 1998 and has grown into a well-established event featuring a marathon, half-marathon and 5K/10K.  The race draws runners from across the Upper Midwest and beyond, welcoming athletes of all ages and abilities.  

Organized by the Ashland Area Chamber of Commerce, the event was created to extend the autumn tourism in the Chequamegon Bay area and highlight the region’s vibrant fall colors.  What began with roughly 300 participants has expanded over the years into a celebration attracting well over a thousand runners annually from across the United States.

The course takes advantage of the Tri-County Corridor rail-trail, an old abandoned railroad line that reflects the area’s rail history and gives the race its name.  The mostly flat, point-to-point course runs from Iron River to downtown Ashland, offering a fast course with scenic views of surrounding forests, farm land, trestles and a finishing glimpse of Lake Superior.

Today, the WhistleStop Race is known for its beautiful fall setting, strong community volunteer support, and runner-friendly atmosphere, Boston Qualifying Marathon and a great race to do your personal best, earning its reputation as a beloved Northwoods autumn tradition and a staple of Wisconsin’s racing calendar.