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About Us

We are celebrating the Annapolis region's maritime history

and our connection to the water

Annapolis has deep roots connected to the water. Local waterways including Spa Creek, the Severn River, and the Chesapeake Bay provide transportation, recreation, and seafood.  The water inspires our food, arts, heritage, and culture. As a port city since colonial times, our maritime history has a wide range of stories. This event will highlight some of the historic boats that worked or played on the waters of the region. 

We hope after your visit you feel more connected to the water, boats, ships, people, art, culture, and heritage that call Annapolis and the Chesapeake area home. 

If you enjoy this event we invite you to visit Chestertown Maryland in late October for the Sultana Downrigging Tall Ships & Bluegrass Festival.

Event Location

Susan Campbell Park, 1 Dock Street, Annapolis, MD


Free Parking at

Calvert Street Parking Garage, 19 St. Johns Street

(Friday evening and all day Saturday and Sunday)

Paid Parking at

Whitmore Parking Garage, 25 Clay Street (Free on Sunday until 4 pm)

Gotts Court Parking Garage, 25 Northwest Street

Free shuttles from the following Annapolis parking garages

Knighton Parking Garage, 1A Colonial Ave 

Park Place Parking Garage, 1 Park Place 

Click here for additional parking tips

Visitor Services

Visitor Center Booth (1 Dock Street) next to Harbormasters office

Visit Annapolis Visitors Center 26 West Street

Lodging Partners

Annapolis Waterfront Hotel, 80 Compromise Street


Flag House Inn, 26 Randall Street

Georgian House, 170 Duke of Gloucester Street


Gibson's Lodgings of Annapolis, 110 Prince George Street

Reynolds Tavern, 7 Church Circle

Arriving by boat

Check with the Annapolis Harbormasters office (1 Dock Street) for docking and mooring options


Pets are not recommended for this event as pets are not allowed on boats and

the asphalt can burn your pet's paws on a warm day. If you bring a pet it must be friendly and leashed.

Waterfront Saftey

This event is next to the water, so make sure you are aware of your surroundings and do not allow kids to roam near the water unattended.


Are available at the Harbormasters office (1 Dock Street)

First Aid

Is available at the Harbormasters office (1 Dock Street)

Rain or Shine

The boats are here rain or shine. If weather affects any portion of the event we will update the website.

Boarding Boats

Some boats will be open to tour. Wear soft-soled shoes if going on deck.

Click the image below to plan a fun downtown Annapolis experience

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