In 2010, the University of Winnipeg and the Government of Manitoba hosted the Arctic Gateway Summit to discuss the regular use of a commercial shipping line running from Winnipeg to Murmansk, Russia via the Port of Churchill and the waters of Nunavut. In this article, I put this initiative in the historical and spatial context of the town of Churchill to help us understand how the Arctic Gateway represents the town’s past and current positioning in Northern transportation and economic development plans. The Arctic Gateway vision echoes various proposals developed since the 1910s for a port on Hudson Bay to become a key link between Western Canada and foreign markets. However, it raises concerns among Churchill’s leaders that the town is shifting from being perceived as a Northern Canadian community to becoming an outpost not quite North enough anymore. Based on archival work and interviews, I utilize community reactions to the Arctic Gateway project to examine how Churchill is positioned in the Canadian geography of transport and Northern development, and to reveal the shift that the community has perceived in recent years in terms of investment and public attention being directed to other, more Northern communities.