Based on the book The Red River Trails: Oxcart Routes Between St. Paul and the Selkirk Settlement, 1820-1870, this article focuses on the symbolic role the trails played in linking two distance cultures (the preindustrial hunting-farming communities in Canada and the growing river town of St. Paul) as well a two geographical areas. Utilizing primary sources, the author explores the various perceptions of the prairie, the trails crossed, and how those perceptions were influenced by the traveler's point of origin and destination.