This article discusses the intersection of two Carteret County residents—Confederate General Robert E. Lee and Elizabeth Oakes Prince Smith, the mother of the infamous Appleton Oaksmith. Lee was responsible for the inspection of forts in North Carolina, and in 1840, arrived at Beaufort. While Lee would spend the next year fortifying Fort Macon, he left for New York City in 1841. At the same time, Elizabeth Oaksmith and family resided in New York City where she met General Lee. The two met and conversed on bravery and their long-term dreams. Eventually, Oaksmith would move to Carteret County where she later wrote on her memories of the General.