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.
Great Annapolis Pumpkins
October 2025. You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Sponsored by Visit Annapolis & Anne Arundel County and coordinated through the Downtown Annapolis Partnership, these gigantic gourds make for the perfect fall...
