Vegetation structure, composition, and community patterns on the landscape of southwest Oregon have changed since Euro-American settlement began in the mid-1800s. Much of this change has been attributed to the transition of land management strategies from those dominated by Native American practices, through the early Euro-American settlement period, and on to the post World War II era of industrial scale timber harvest and fire suppression. Using homestead patent applications and associated land classification maps generated under the Forest Reserve Homestead Act of June 11, 1906, we add to the understanding of historic vegetation conditions and evaluate vegetation change over time for land applied for by homesteaders in the Applegate River watershed of southwest Oregon. These homesteads were predominately located on areas now supporting chaparral, Pinus and/or Quercus woodlands, mixed conifer forests, pastures, and agricultural land. Our study presents primary source documentation that describes stands dominated by broadleaf trees and shrubs as dense at the time of patent application, contrary to the assumption that such stand structures are an artifact of fire suppression efforts of the last century. Historic vegetation polygons cross tabulated with current classified imagery in GIS indicate that conifer forests and shrublands each retain most of their former extents within their same locations on the landscape. The persistence of shrub stands to current times implies longer-term stability of these communities and indicates that a transition to conifer domination is not evident in all shrublands.