In this lecture, attendees will explore the complex movement of ancestors who entered North America through Canadian ports before migrating south to the United States. While many researchers focus on major U.S. seaports, this session examines why many forebears chose routes through the Maritime Provinces and Quebec City, often crossing the border multiple times and creating a diverse trail of records. Participants will learn how to navigate historical geography and boundary changes, alongside practical strategies for locating digitized passenger lists at Library and Archives Canada (LAC) and border crossing records from the National Archives (NARA). By examining the historical context of groups such as the Acadians, Loyalists, and Home Children, researchers will gain a comprehensive framework for tracing these overland migration patterns and understanding the documents created by ancestors who moved between both nations.