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Annapolis Holiday Market
getting there


We recommend heading straight for one of the parking garages listed below and plan on spending the day in downtown Annapolis. This is the easiest and most stress-free way to visit downtown Annapolis, Maryland. There is a ton of shopping, dining, entertainment, and attractions within an easy walk from the Annapolis Holiday Market. If planning on bringing a large group, tour buses can drop off at the entrance to the Annapolis Holiday Market. Street parking has strictly enforced time limits.


Annapolis Holiday Market Location

1 Dock Street, Annapolis, MD 21401

Free Parking at

Calvert Street Parking Garage, 19 St. Johns Street

(Open every weekday evening by 6 pm and all day Saturday and Sunday)

Commercial Streets downtown is free for 2 hours if using the Parkmobile App.

Sunday only: Free parking at Hillman Parking Garage if you exit by 2 pm 

Sunday only: Free parking at Whitmore Parking Garage if you exit by 4 pm 

On-street parking on commercial streets is free for the first 3 hours.

Paid Parking at

Hilman Parking Garage 150 Gorman Street. (first hour free if using the Parkmobile app)

Gotts Court Parking Garage, 25 Northwest Street

Whitmore Parking Garage, 25 Clay Street ($6 until 4 pm and $2 after 4 pm and Free on Sunday until 4 pm)

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

Downtown Annapolis Shopping, Dining, Tours and entertainment options

Click here for more information

Visitor Services

Visit Annapolis Visitors Center 26 West Street and the Visitors Kiosk at the event.

Group Travel

Bus and Tour Groups are welcome. If your group likes free admission to Christmas Markets and Kris Kringle Markets this event is for your group. Large groups needing help with lodging or dining can contact Elizabeth Joyner, Visit Annapolis Director of Group Travel 410-280-0445, ext. 306

Dining Partners that can handle large groups with advance reservations and located within a block or 2 of the holiday market are

Latitude 38, Iron Rooster, Middleton Tavern, Annapolis Market House, McGarvey's Saloon, Federal HouseBuddys Crab and Ribs, and Obrien's Restaurant, ​

Lodging Partners with a short walk to the holiday market

134 Prince Boutique Hotel,134 Prince George Street

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

Historic Inns of Annapolis, 58 State Circle

Reynolds Tavern, 7 Church Circle

Arriving by boat

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


Busy venues like this are not the best venue for pets. We recommend that they be left at home. If you bring a pet, it must be friendly and leashed.

Waterfront Safety

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, Snow, or Shine

This event is rain, snow, or shine. If the weather affects any portion of the event, we will update the website.


The map below highlights parking garages and the Annapolis Holiday Market location.

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