In 2000, Leah Roberts abandoned her life to embark on a journey inspired by Jack Kerouac's 'On the Road,' leaving behind journal entries and notes that suggested a planned adventure. Her wrecked car was found in Washington state, but she had vanished. We examine her final writings, bank transactions, and witness accounts from her last known locations. The episode delves into the literary connections in her farewell messages, analyzing whether her disappearance was a planned escape or something more sinister.