An examination of the city of Calgary and its culture requires that we look through the lens of the double image — one-half ‘cowboy’, one-half ‘urban dweller’. To explore this image further, this thesis proposes the development of a dude ranch called the Carousel Hotel, a resort that will encircle the recently approved Springbank Reservoir on the outskirts of the city on a strip of land affectionately known as ‘The Cowboy Trail’. Here at the intersection of Highway 1 and Highway 22, old meets new. Drawing on architectural memory and the cinematic, this project circles the wagons as a means to question our understanding of nostalgia, whimsy, and the dusty trails in-between.