Things to Do Events & Festivals

Midnight Madness

3 Church Circle, Box #210, Annapolis, Maryland 21403

About Midnight Madness

Midnight Madness is a local holiday shopping tradition in the heart of the city of Annapolis. Streets and storefronts will be adorned with holiday decorations, trees, garland, snowflakes, bows and lights along with performers in the streets and in-store refreshments and entertainment. The festivities and shopping take place along Maryland Ave, State Circle, West Street, Main Street, Market Space, Randall Street and Dock Street. Residents and visitors are invited to stroll throughout downtown Annapolis from 5PM until Midnight on Thursdays, December 5th and 12th and 5PM until 11PM on December 19th. Free Annapolis Parking is plentiful during the Midnight Madness. Free parking all evening at Calvert Street Garage - 19 St Johns St. Free parking all evening at John Whitmore Garage - 25 Clay St. Free parking for 3 hours at all metered spaces when you use the promo code ParkDTA in the Parkmobile App Discounted $5 parking is available when you prepay online at for Knighton Garage - 1A Colonial Ave Park Place Annapolis Garage at 3 Park Place $6 all-day parking is available at Amos Garrett Garage at 275 West Street. The free circulator shuttle runs about every 10 minutes on West Street / Annapolis Arts District, Calvert Street, State Circle, and Main Street to make it easy to get around town. It now stops by every downtown parking garage, just waive it down anywhere along its route and climb aboard. You can see its location at Ranked as one of America’s top 25 best towns for the holidays by Travel + Leisure, Annapolis, the perfect place to get into the spirit of the season