A Photographic Reconsideration of the Oregon Trail calls on the historical and contemporary iconography of the Trail, represented by the ruts created by wagons that often parallel today’s freeways, the communities that honor their roots tied to the Trail, and the depictions celebrating those who blazed a path for 2,000 miles to stake their claim. For years I have traveled many sections of the Oregon Trail, creating my story along the way. It is a part of my journey—influencing my life, from my ancestor’s migration to my own. The Oregon Trail celebrated its 175th anniversary in 2018. It is the largest American migration where pioneers took tremendous risks venturing into unknown territory on primitive thoroughfares seeking the promise of a better life. This work characterizes our interaction with the Oregon Trail from start to finish as tourists, artists, historians, and preservationists.