Annapolis, Maryland Calendar of Events

Annapolis is a feast of things to do year-round.  The biggest in-water sailboat and power boat shows in the United States take place in October a block from Flag House Inn.  Make Flag House Inn your destination then and for other special events listed below.  For Naval Academy events, see that page.

Annapolis Sailboat and Power Boat Shows

Simply no better way to beat the Boat Show congestion!  Just a block away & parking too!” Ideal for vendors and buyers alike.

At Flag House Inn you are only a block from the main entrance at City Dock.  You can come back from the show at any time and return in a moment. And it’s easy to explore & enjoy Annapolis’ nightlife at your ease.

At Flag House Inn you enjoy:

  • Hassle-free, on-site parking at no extra cost.
  • King-size beds for extra comfort.
  • In-room full bathrooms and cable TV.
  • Good seating and plenty of lighting for reading.
  • Large assortment of books & magazines. 
  • Unique two-townhouse floor plan assures privacy.

Summer concerts at the City Dock

Every Tuesday evening from early July through mid-August walk to the City Dock (a two-minute walk) and enjoy the US Navy Band present a free concert for you.


Monday – Friday during the academic year see the midshipmen during noon meal formation at Bancroft Hall.

View Friday afternoon formal parades on the Navel Academy Parade Ground – Worden Field.


On July 4th enjoy our small town parade followed by US Navy Band concert and then at dark oh and ah at the fireworks display over the water.

On New Year’s Eve enjoy music, dancing, food and fun during the evening and then fireworks over the water at midnight.

Outdoor summer theater

From June through mid-September on Thursday – Sunday evenings enjoy our outside Summer Garden Theater nestled in the heart of downtown just a five-minute walk from Flag House Inn.  An experience you are sure to enjoy.

Quiet Waters Park

Saturday evenings in July and August enjoy outdoor concerts in this lovely setting.  About a 10-minute drive from Flag House Inn.  Admission/car charge