From fine art galleries and live music venues to performance arts studios and festivals, Annapolis offers a little something to art-lovers no matter the time of year. Here’s a quick breakdown of what you can expect in Annapolis’ thriving arts and culture scene when you visit.


Spring is the perfect time to wander around town. So, what better way to bring in the spring than with a film festival spread across the city? First held in 2013, the Annapolis Film Festival has become one of Annapolis’ most anticipated events, showcasing over 70 local, national, and international films. Along with documentaries, full-length features, and short films, the four-day event also features lectures with filmmakers and screenwriters. It’s the perfect event for film junkies. 

Maryland Ave Spring Festival

Spring also brings about the beginning of the beginning of festival season. The First Sunday Arts Festival is held on the first Sunday of each month (from May through December) on the first block of West Street. The festival features live music, food, and of course, art. There’s also the Maryland Ave Spring Festival, similar to First Sunday, where artists from all over Maryland line the street selling their work to passersby. Both festivals are a great excuse to get outside, walk around the city, and purchase some great art. 


Summer is packed with music, theatre, and art. Primarily featuring local musicians, festivals like the Annapolis Irish Festival and the Nextival offer visitors a great peek into the area’s talented performers. The Arts and Wine Festival is another summer favorite, offering local artists the chance to display and sell their art while visitors sample tasty Maryland wines. 

Photo by Joshua McKerrow.

May marks the start of Comedy in the Courtyard at Reynolds Tavern. Put on by the Annapolis Shakespeare Company, Comedy in the Courtyard is a must for all theatre enthusiasts. Here, visitors can enjoy a performance by one of the area’s most acclaimed studios, all set outside in the historic patio of Reynolds Tavern. The shows run through September, so there’s plenty of time for you to catch a performance.

Paint Annapolis

Paint Annapolis is another great, weeklong event in Anne Arundel County. Each year, artists from all over descend on the county for a juried plein air painting bonanza. Wander around Annapolis and you’ll see artists showcasing their craft, painting the landscapes, seascapes, and architecture around town. The event culminates in a public reception and award ceremony before paintings can be bought by the public. It’s a unique event where the public can view a painting as it’s being created, then actually purchase it at the end of the event. 


Autumn in Annapolis is a great time to browse through the city’s 20-plus art galleries. All within a short walk from one another, you’ll find galleries selling sculptures, paintings, ceramic artwork and everything in between. It makes for the perfect time to get a jumpstart on holiday shopping for the art-lover in your life. 

McBride Gallery


The winter months are a great time to experience the world-class theatre available in Annapolis. The Ballet Theatre of Maryland is one of the area’s favorites for performing arts. Shows like the Nutcracker and Sleeping Beauty are perfect for the whole family. There is also the Annapolis Shakespeare Company’s performance of the holiday classic, It’s a Wonderful Life. 


If live music is more your speed during the winter, there are a number of live music venues across Annapolis that host local musicians each night. Rams Head on Stage is the largest in town, playing host to national and local acts each and every night. If you’re looking for a larger venue, head up to Arundel Mills where you’ll find Rams Head Center Stage located inside the Maryland Live! Casino.