Name: Midnight Madness in Downtown Annapolis 2025
Start: 2025-12-18T16:00:00-05:00
End: 2025-12-18T23:00:00-05:00
Location: Downtown Annapolis

Midnight Madness in Downtown Annapolis 2025

Shop local during Midnight Madness on December 4th and 11th, from 4 pm until Midnight, and on the Eleventh Hour on December 18 until 11 pm at 90 stores and 80 restaurants in downtown Annapolis, rated by many in the press as a Top 10 Christmas Town destination. These are fun nights to shop local.
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, light canopies, a large Christmas tree, and a menorah. This will create a fun, safe, outdoor environment for late-night shopping and dinner with your family. On-street entertainment will be throughout downtown Annapolis. On the third Midnight Madness (Dec 12), you can also enjoy the Annapolis Holiday Market at St John's College front lawn from 4pm to 9 pm.
The easiest and best parking deals for all evening are at the Calvert Street Parking Garage (19 St Johns Street) from 6 pm to 6 am, where parking is free all evening, and at the Whitmore Parking Garage (25 Clay Street), where parking is just $2 all evening from 4pm to 6am. You can also find 2-hour free parking (2-hour limit is strictly enforced) on commercial streets when you use the Park mobile App.
The free circulator bus will pick you up and take you downtown with pickups at the Park Place Parking Garage and the Knighton Parking Garage, both located off of West Street. On-street metered parking spaces on commercial streets are free for short-term parking.
For additional information on Midnight Madness, lodging, shopping, restaurants, and downtown Annapolis events, visit the Downtown Annapolis Partnership’s website