The Bayfield Winter Festival started in 2006 as a fundraiser for the Recreation Center. Initially called Manypenny Madness, it covered approximately three blocks and included a Polar Plunge, sledding down Manypenny Avenue, broomball, and a benefit dinner at Maggie's. All proceeds were donated to the Rec Center. The event has grown substantially each year. This year's events take place all over Bayfield as well as at nearby Mt Ashwabay and Legendary Waters Casino.