December 9, 2023
Annapolis, US 50 F

7 must-do events in Annapolis this May

What’s happening in Annapolis and Anne Arundel County in May? Plenty! With finals out of the way, thousands of midshipmen donned in their dress whites are out and about in downtown Annapolis – on the streets, in restaurants and shops, along City Dock. There’s an excitement in the air as the community celebrates our nation’s newly minted Navy and Marine Corps officers. To make it easier to enjoy the sights and sounds of May in Maryland’s capital city, Visit Annapolis and Anne Arundel County is highlighting seven events you won’t want to miss!

  1. Some say it’s the most beautiful day in Annapolis! Come, camera in hand, and capture door after door of baskets filled with colorful spring flowers during the 63rd Annual May Day Basket Competition. May 1.
  2. Shop among the creations of 130 local and regional artisans; dine at outdoor cafes; and enjoy several live bands during the 17th Annual First Sunday Arts Festival. May 5 and every first Sunday through November 3.
  3. Runner’s World Magazine calls the Maritime Republic of Eastport .05K Bridge Run “the least challenging athletic event ever conceived.” May 11.
  4. After four years of 24/7 work and commitment, graduating midshipmen are commissioned as officers in the U.S. Navy and Marine Corps during Commissioning Week festivities. The celebration includes concerts, a formal parade, the Herndon Monument climb, and a Blue Angels flight demonstration. May 17-May 24. See full schedule here.
  5. Celebrate the men and women who made the ultimate sacrifice for our country at the Annapolis Memorial Day Parade. May 27.
  6. Spend Wednesday evenings dining, dancing and enjoying live music beneath a canopy of lights at Dinner Under the Stars. Restaurants offer international and hometown flavors. May 29 and every Wednesday through September 18.
  7. Capture a taste of Athens at the Annapolis Greek Festival. May 30-June 2.
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