Jake and Nate delve into the fascinating history and mystery surrounding the Lost Colony of Roanoke. Starting with light-hearted reflections on the Oregon Trail game, they transition to a detailed discussion on the failed English attempts to establish a permanent settlement in America before Jamestown. They highlight the two main colonization attempts between 1585 and 1587, led by Sir Richard Grenville and John White, respectively. The podcast covers the colonists' initial troubles, interactions with Native Americans, and the eventual disappearance of the settlers, leading to various theories and historical investigations. Sprinkled with humor, trivia, and casual banter, Jake and Nate make history engaging and entertaining.