Winter on The Chesapeake
Known for its cozy coastal charm, historic streets, and waterfront views, Annapolis is consistently ranked as one of the best holiday destinations in America. Explore our guide to the best holiday events and start planning your winter getaway to Annapolis and Anne Arundel County.
Annapolis Chocolate Binge Festival
The Annapolis Chocolate Binge Festival takes over the first block of West Street, in a family-friendly celebration of all things cocoa. 2025 marks the 11th year of the event, and some new activities are coming your way!
Bay Bridge Run
The Bay Bridge Run is a 10K race that provides the perfect opportunity for runners, walkers, and spectators alike to race across the Cheasapeake Bay Bridge’s eastbound span from Anne Arundel County to Kent Island to Queen Anne’s County.
