Midnight Madness

A Festive Shopping Celebration in Downtown Annapolis 

The first two Thursdays of December from 6pm until Midnight and the third Thursday of December from 6pm until 11pm


Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garland, snowflakes, bows and lights to create a Downtown Winter Wonderland.


Residents and visitors are invited to stroll along Main Street, West Street, Maryland Avenue, State Circle, and Dock Street from 6 PM until Midnight to support our local businesses. When we Shop Local, we reinvest in our community and help our downtown businesses thrive. Check out all the stores, galleries, and boutiques along West Street, Maryland Ave, State Circle, Main Street, Market Space, Randall Street, and Dock Street.


A very special thank you to our premier sponsor, Sheehy Lexus of Annapolis for their ongoing support!


Some of our Featured Attractions:

  • Holiday Light Canopy over West Street / Annapolis Arts District & Maryland Ave.

  • Snowflake Alley: A magical passageway to a delightful evening of fun, entertainment, shopping deals and treats to eat. | Main Street (Cabbage Alley)

  • Holiday Christmas Tree at Market Space 

  • Our historic, brick-lined streets will be full of carolers, choirs, musicians, and other street performers. We will offer fun photo opportunities for all ages.

  • Downtown merchants may offer complimentary refreshments, specials, shopping incentives and a personalized approach to customer service that is certain to create a delightful sense of community and belonging. Please join us!


To make your experience more enjoyable:

  • The Calvert Street Parking Garage is Free Parking between 6 pm and 6 am. Located  at 19 St Johns Street

  • Use the Park & Shop program is earn free parking at Hillman, Gott's Court, Park Place and Knighton Parking Garages.

  • The Whitmore Parking Garage is free from 4 pm to 6 am. Located at 25 Clay Street.

  • $5 parking at Gott's and Knighton Parking Garages when you prepay at www.annapolisparking.com 

  • Free Circulator buses run along West Street, Calvert Street, State Circle, and Main Street.  

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