The WhistleStop Marathon and Half Marathon is an annual road running competition held in October in Ashland, Wisconsin, in the United States. The course runs point-to-point and is held on the Tri-County Corridor, a rail-trail now paved with limestone gravel. The course stretches from two miles east of Iron River, Wisconsin and features ten re-decked railroad trestles, wetlands, trout streams, Chequamegon National Forest woodlands, dairy farms, residential neighborhoods and traffic-free quiet. The finish is located near Ashland's Bay Area Civic Center. The WhistleStop Marathon is USATF certified (#WI98019WG).
The WhistleStop Marathon and Half Marathon was first run in 1997. In 2006 the marathon accommodated 600 runners while the half marathon accommodated 1,000 runners.