Rickey Chernik

Board Member

Rickey grew up in southern Wisconsin but truly fell in love with the Driftless Area after meeting his wife, whose family has deep roots in Iowa County. The region’s rugged topography, winding valleys, and sense of place quickly became central to both his personal life and his professional passions.

Rickey is an avid trail runner and the owner of a local trail‑running organization, Driftless Endurance, where he designs events that highlight the unique terrain and character of the Driftless. His professional background spans events, marketing, operations, and project management, and he’s especially interested in work that connects people to the outdoors in practical, hands‑on ways. He’s also passionate about the Driftless Trail project and the opportunities it creates to help more people experience the landscape.

Outside of work, Rickey enjoys building and maintaining trails on his family’s land and spending time exploring new routes throughout the region. He values the mix of physical work, creativity, and stewardship that trail building offers.

Rickey lives in Middleton with his family and two German Shorthaired Pointer, and he’s grateful to be part of a community that cares deeply about the Driftless and its future.