Celebrate Maryland Day

Family-friendly Walking Tours & Cruises in Annapolis

Maryland Day Weekend is a unique heritage-based group of events in Annapolis and southern Anne Arundel County. Maryland Day celebrations are a hit with family and friends getting together to experience the local history, culture and heritage of the region…Maryland Day commemorates the formal founding of the colony of Maryland, when the newly arrived colonists erected a cross on St. Clement’s Island, offered prayers (perhaps by saying Mass), and took “possession of this Countrey for our Saviour and for our soveraigne Lord the King of England.” Information provided by Maryland Day.

“The Everything” Walking Tour

  • Saturday, March 21st 1:00pm-2:30pm
  • Tour Departure Location: 25 Market Space 
  • Free event (Walk up tickets may be available.)

Join Mistress Mary as she leads guests through an entertaining stroll of the Historic District. You’ll get a little history, a splash of scandal, some mysterious ghost stories, and much more on this entertaining sampler of Watermark’s various walking tours.

Reserve Spot

Annapolis Street Art Walk

  • Sunday, March 22nd 1:00pm-2:30pm
  • Tour Departure Location: 188 Main St.
  • Free event (Walk up tickets may be available.)

Art is all around in Annapolis…if you look for it! Follow your guide through the historic streets to discover the brilliant work of artists, without ever entering a gallery. Hidden treasures await you with murals, sculpture, statues, and small art works that are not only beautiful, but meaningful as well. 

Reserve Spot

Maryland Day Annapolis Harbor Cruise

  • Date: Monday, March 23
  • Time: 4:00pm
  • Tour Departure Location: The Piers At 1 Prince George Street
Buy Tickets

Maryland Day Annapolis Harbor Cruise

  • Date: Tuesday, March 24
  • Time: 4:00pm
  • Tour Departure Location: The Piers At 1 Prince George Street
Buy Tickets

Maryland Day Annapolis Harbor Cruise

  • Date: Wednesday, March 25
  • Time: 4:00pm
  • Tour Departure Location: The Piers At 1 Prince George Street
Buy Tickets

Maryland Day Celebrations March 19-25, 2026

Learn More about Other Maryland Day Celebration Events across the City and the County by visiting: https://marylandday.org/plan-your-visit/