The Tower of London, a historic landmark and UNESCO World Heritage Site, has stood for nearly 1,000 years as a royal palace, prison, and symbol of British history. Its imposing walls housed some of the most infamous prisoners in history, but not all stayed confined. Tales of daring escapes, such as those of John Gerard, who fled using a rope smuggled into his cell, or the Earl of Nithsdale, disguised in women’s clothing, add an element of intrigue to its legacy. These incredible stories highlight both the resilience of the prisoners and the Tower’s fascinating past as a place of both oppression and ingenuity.