Paint Annapolis is a premier plein-air painting festival held annually in Annapolis, Maryland, celebrating the city’s rich maritime heritage and vibrant arts scene. Hosted by the Maryland Federation of Art, this week-long event brings artists from across the country to capture the charm of Annapolis through open-air painting. Visitors can watch artists at work, attend gallery exhibits, and even purchase original artwork showcasing historic streets, waterfront views, and lively cityscape.