Experience
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Spring Happenings in Annapolis
As the days grow longer and the harbor awakens, Annapolis moves with the rhythm of the season. Sailboats return, flowers line the streets, and the city comes alive with tradition, film, and celebration. Here’s what’s ahead this spring.
18th Annual Maryland Day Celebration Weekend
March 22-23, 2025
History is at home in Annapolis. This spring, over 40 historic sites open their doors for just one dollar—or free. Walk the halls of the William Paca House & Garden, watch living historians bring the past to life on Pinkney Street, and explore four centuries of maritime tradition at the Museum of Historic Annapolis.
Annapolis Film Festival
March 27–30, 2025
For four days, Annapolis turns into a storyteller’s city. Independent films, documentaries, and global cinema light up the screens of historic venues downtown. Between screenings, meet filmmakers, take part in discussions, and watch the Chesapeake Bay set the scene.
Annapolis Spring Sailboat Show
April 25–27, 2025
Spring on the water starts here. The harbor fills with catamarans, monohulls, and family cruisers, while industry experts and seasoned sailors gather to talk boats, gear, and the season ahead. Step aboard, explore what’s new, and celebrate the return of sailing.
May Day in Annapolis
May 1, 2025
On the first of May, Annapolis comes alive with color. For nearly 70 years, homes and businesses throughout the historic district have adorned their doorsteps with vibrant baskets of fresh-cut flowers in a beloved springtime tradition. Stroll the cobblestone streets, take in the artistry of each unique arrangement, and embrace the beauty of spring on full display.
Celebrate a City in Bloom
Spring Awaits on the Waterfront
As the harbor awakens and the city comes to life, spring in Annapolis invites you to slow down, look around, and take it all in. Stay in the heart of it all and let the water set the pace.