What’s Happening in Annapolis This May?
May in Annapolis brings together waterfront charm, local traditions, and a full lineup of events worth getting out for 🌊 From festivals and markets to live entertainment and community celebrations, there’s something happening all month long in and around the city.
Annapolis Book Festival
May 2nd
Kick off the month with a day dedicated to stories, ideas, and community at the Annapolis Book Festival 📚 Held on the beautiful Key School campus, this event brings together authors, readers, and speakers for engaging talks, book signings, and family-friendly activities. It’s a relaxed, inspiring way to spend a spring day.
First Sunday Farmers Market
May 3rd
There’s nothing better than a farmers market in the spring 🌿 The First Sunday Farmers Market features fresh produce, local goods, and a welcoming atmosphere that makes it easy to slow down and enjoy the morning. Whether you’re shopping or just browsing, it’s a great way to support local vendors.
Brewgrass in the Barn
May 9th
Live bluegrass, local brews, and a rustic setting come together at Brewgrass in the Barn 🎶🍻 This event blends great music with a laid-back outdoor vibe, making it perfect for a casual day out with friends. It’s one of those events where you can settle in, listen, and enjoy the atmosphere.
Comedy Murder Mystery
May 21st
Looking for something a little different? The Comedy Murder Mystery delivers an interactive night of laughs, suspense, and entertainment 🎭 Follow along, piece together clues, and enjoy a unique experience that’s part comedy show, part whodunit. It’s a fun night out in downtown Annapolis.
Annapolis Irish Festival
May 29th & 30th
Celebrate Irish culture with a weekend full of music, dancing, food, and community ☘️ The Annapolis Irish Festival is lively, welcoming, and packed with entertainment that keeps the energy going all day. Whether you’re there for the performances or the atmosphere, it’s a standout event to close out the month.
Paint Annapolis
May 31-June 7th
Wrap up May and head into June with Paint Annapolis, a week-long celebration of art and creativity 🎨 Artists set up throughout the city to capture Annapolis in real time, creating a unique, ever-changing gallery experience. It’s a great way to explore the area while taking in some incredible local talent.
