Since its colonial days, Annapolis has been a hub for both artists and art enthusiasts. Today, there remain lots of ways to experience art in Annapolis. You can visit any one of over two dozen art galleries, or gaze at public art throughout the downtown district. But perhaps the most fun and lively way to engage in the Annapolis arts community is by attending one of the several arts-oriented festivals that take place throughout the year. Here are some that you may want to put on your calendar today. 

First Sunday Arts Festival 

The First Sunday Arts Festival has become a much-anticipated seasonal tradition in Annapolis. Started in 2002, the charming street festival held in Annapolis' Arts District is an event where the community and arts “fuse.” Held on the first Sunday of each month from May to November, this festival is a free entertainment showcase slash arts and crafts show featuring some hundred artists selling creative, unique wares. You’ll find plenty of entertainment, with live music, dance, theater, and street performers. Bring your appetite: West Street cafes and festival food trucks serve up delicious menu items during the festival. 

Paint Annapolis

Annapolis is a picturesque town that inspires artists to capture its beauty. And one week each year, Annapolis encourages artists from across the country to do just that. Paint Annapolis is a five-day juried plein air painting competition during late spring in which artists from across the country descend on Annapolis, set up their easels outdoors, and allow passersby to look over their shoulders while they work. The competition component occurs at the end of the festival. Whether you’re a plein air (outdoor) painter or an enthusiast of the artistic form, this festival’s for you. 

Annapolis Film Festival

The annual Annapolis Film Festival in early spring brings to our town a four-day line-up of critically acclaimed feature and short films from around the world. The films include compelling narratives and documentaries. Some are Academy Award nominees. Several are fresh from Sundance and South by Southwest. In addition to showcasing riveting films, the festival offers panelists and lectures that take movie viewers “behind the scenes”. More than seventy films are presented, all at venues in downtown Annapolis within walking distance of each other. Guests may also catch a ride on the City Circulator bus.

Annapolis Arts & Wine Festival

Does sipping wine from local wineries, listening to jazz, and enjoying the work of the region’s finest artists and craftsmen sounds appealing? Then come to the Annapolis Arts & Wine Festival. Conveniently located at the Navy-Marine Corps Memorial Stadium, the festival presents the perfect way to kick off the summer. View the works of over 200 of the region's best artists and craftsmen employing a variety of media including painting, sculpture, ceramics, digital art, mixed media, printmaking, jewelry, fiber art, glass, wood, leather, metal and photography. Sample wines from more than 25 Maryland wineries in our wine pavilions. Purchase a bottle of wine and relax while listening to smooth jazz all day long. Bring the children, too, for activities in the Kids' Art area including theatrical, dance, and musical performances on stage.