The Cottonwood River Watershed is located in southwestern Minnesota, draining 1,310 square miles of land within the Minnesota River Basin. The watershed is comprised of parts of Brown, Cottonwood, Lyon, Murray, and Redwood Counties. This essay gives a brief account of the initial European settlement of the area and the establishment of the current political boundaries. It then focuses on the major developments in agricultural production during the past 150 years, touching on the changes in landscape and wildlife due to drainage and restructuring of water bodies and the clearing of forest land.