March 4, 2024
Annapolis, US 46 F

Are You Ready for Midnight Madness in Annapolis?

The first three Thursday nights in December are the biggest and most fun nights of the year to shop in downtown Annapolis.  It’s the annual Midnight Madness shopping nights on December 7, and 14, when stores and restaurants stay open until Midnight, and on December 21, the Eleventh Hour they stay open until 11 pm at about 90 stores and 80 restaurants in downtown Annapolis, Maryland.

The downtown Annapolis area, including West Street, Maryland Ave, Main Street, and the City Dock area will be filled with traditional holiday decorations, including beautiful storefront windows, garland, wreaths, holiday lights, a snowflake alley on Main Street, light canopies over Maryland Ave and West street, a large real Christmas tree, and a menorah near the Market House.

“The local shops and restaurants are ready for you to enjoy late-night shopping and dinner with your family,” says Erik Evans Executive Director of the Downtown Annapolis Partnership. “You will find that downtown Annapolis is a vibrant, and festive place to shop. When you add in the on-street entertainment, you will understand why Annapolis is rated as one of the top Christmas towns in the nation.” 

Several new shops can be found this year on West Street, Maryland Ave, Fleet Street, and Main Street alongside your favorite long-time businesses. The Downtown Annapolis Partnership Ambassadors will be out strolling the sidewalks to assist visitors with directions, parking questions, etc. 

For the first Midnight Madness (Dec 7) you can also enjoy the opening night of Annapolis Holiday Market on City Dock from 4 pm to 10 pm. The Dec 21st Midnight Madness is perfect for procrastinators as it is the Eleventh Hour of the shopping season. 

Free and discounted parking is abundant during the holiday season in downtown Annapolis. The Calvert Street Parking Garage (19 St Johns Street) has free parking Monday through Friday from 6 pm to 6 am, and free parking all day Saturday and Sunday.  The City of Annapolis is offering 2-hour free parking on commercial streets when you enter the code ParkDTA in the Park mobile App. and the first hour is free parking in the new Hillman Garage on Gorman Street when you use the Parkmobile App. Whitmore Parking Garage (25 Clay Street) is offering $2 parking every day from 4 pm to 6 am. The free circulator bus is operating extended late-night hours during all Midnight Madness events and will pick you up and drop you off at the Park Place and Knighton parking garages and take you downtown. 

For additional information on Midnight Madness, lodging, shopping, restaurants, sponsors and other downtown Annapolis events visit the Downtown Annapolis Partnership’s website at  

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