Every December, the city of Annapolis, Maryland, transforms into a festive wonderland for one of its most beloved traditions — Midnight Madness Annapolis. This annual event captures the true spirit of the holidays with twinkling lights, cheerful music, and late-night shopping that brings the entire community together. Whether you’re a local resident or visiting for the season, Midnight Madness Annapolis is an unforgettable experience that combines small-town charm, holiday cheer, and the joy of supporting local businesses.