This paper investigates the Canada–US borderlands relationship along the two geographic corridors as bounded by Lake Superior: Sault Ste. Marie, Ontario–Sault Ste. Marie, Michigan and Thunder Bay, Ontario–Duluth, Minnesota. Borderland communities—driven by their shared cultural characteristics (ethnicity, language,religion)—are said to challenge the border as a dividing device and undermine the very essence of international borders. Moreover, borderlands regions are dynamic and overlapping, providing the first point of contact and interaction between nations. Our results depict inherent differences between these particular border regions, with each illustrating characteristics that both connect and divide. Despite the passage of time and both countries’ determined efforts to make the passage safe and less demanding, the peoples in these border regions perceive a continuing frustration with crossing the border and connecting to the people on the other side of the border.