West Street will feature vendors and performances throughout the day, as will Maryland Avenue and State and Church Circles.
Lots of street festivals promise something for everyone, but Arts Annapolis 2026 is aiming to raise the bar. Organizers are planning a dazzling city-wide display of art, live music, and performances that will stretch from Maryland Avenue to State and Church Circles and up West Street to Calvert Street. Designed to delight, inspire, and entertain, the free event is scheduled for Saturday, June 13 from noon to 10 p.m.
“This is a real celebration of arts and culture—more than 60 visual artists, vendors, authors, buskers, choral groups, stilt walkers, dueling pianos, drummers, tango dancers, and more,” says Don Lamb-Minor of the Annapolis Arts District, who’s helping to coordinate the event. “We not only have Ballet Theatre of Maryland and the Annapolis Opera representing the city’s professional arts groups, but we’re also showcasing an amazing collection of international musicians for a global vibe.” The program will include Afro-Caribbean, bluegrass, jazz, Latino, Turkish-Indian, and island music, with bands performing on stages throughout downtown and in informal sidewalk sessions.
Al fresco dining is scheduled for the evening, with performances continuing on the Calvert Street stage.
Visual artists will demonstrate their technique and sell their work at this year’s festival.
Many of the offerings will be interactive, connecting artists and audiences through demonstrations and free activities. Darin Gilliam of AND Creative points out, “There’s a focus on local visual artists who are making really beautiful, dynamic, contemporary artwork. This isn’t only sailboats and maritime art, which Annapolis is well-known for. There’s more diversity, more for kids, more for communities, with everyone engaging with the art and being involved.”
Melissa MacMichael, a wildlife artist inspired by the Chesapeake, will demonstrate her painting prowess while she displays her work. She says she enjoys sharing her creative experience. “When I’m painting in the studio, it’s a very immersive process. I’m trying to capture what it might feel like to exist in that space.
“When I paint live, it’s a completely different energy. It becomes much more open and playful; people stop, watch, ask questions, and kids especially are drawn in right away. I love that because it breaks down the idea that art has to be serious or intimidating. Instead of just seeing a finished piece, people are part of it as it’s happening, which makes it feel more immediate and alive.”
At stations around town, adults and kids can channel that energy through printmaking, painting mini-canvases, and drawing chalk murals. Or they can attend demonstrations of less-traditional artforms, including fused glass and laser etching.
For a continuous flow of creativity, head over to the People’s Park Youth Stage on Calvert Street, where the playbill includes performances from Class Act Performing Arts, Naptown Sings, and School of Rock. At St. Anne’s Churchyard, see performances by the Chesapeake Youth Symphony Orchestra, vocalists from Severna Park High School, and a barbershop chorus.
Literary arts will share the spotlight, too, with author-artist Roxie Munro reading from her new book, Treasure Thieves on the High Seas: Pirates, Privateers, and Plunder—a nod to Annapolis’ seafaring history. Created especially for young swashbucklers, it’s a compendium of pirate lore and fun facts, which Munro will share in her appearance at the Annapolis Collection Gallery on West Street.
Dueling pianos will face off during Arts Annapolis 2026.
In addition to two shows by the artists of Ballet Theatre of Maryland, the festival will present the return of Tango on the Dock, an area troupe that specializes in the sensuous Argentine dance form. The group, known for its performances in previous years at City Dock, will appear at the Calvert Street stage from 4 to 8 p.m. Accompanied by a live trio as well as recorded music, dancers will be demonstrating the steps and inviting audience members to join in.
West Street, Calvert Street, and Maryland Avenue will be closed to traffic for the event, and restaurants along West Street will roll out tables and seating for evening dining (a la Dinner Under the Stars). Capping a full day of performances next to Stan & Joe’s and Wiseman Park (next to the Visitors’ Center on West Street), the evening promises to be a grand finale to an arts extravaganza.
Learn more at the Annapolis Arts District website, annapolisartsdistrict.org.
