During the winter of 1812, a pilot boat drifted ashore at Kitty Hawk with a woman’s belongings on board. The crew and passengers were not present and local residents salvaged goods from the vessel, including a painting of young woman. In 1869, the portrait was given to a local physician as payment. The physician found the portrait similar to images of Theodosia Burr, daughter of Aaron Burr, who had disappeared while traveling off the North Carolina coast in 1812. While the portrait’s subject has not been positively identified, the author posits the questions of what if the vessel ashore was carrying Theodosia Burr.