Midnight Madness

A Festive Shopping Celebration in Downtown Annapolis 

Dec 3, 10, and 17, 2020

The first two Thursdays of December from 4 pm until Midnight and the third Thursday of December from 4 pm until 11 pm


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 4 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.

To make these annual shopping nights safe during COVID, stores will be limiting the number of people inside stores to 50% of capacity. We also ask everyone to wear a facemask, to bring hand sanitizer so you can wash your hands frequently and stay home if you are sick.

We are also starting the event earlier at 4 pm so shoppers can stagger their arrival time to either early and later hours when it is less busy. Many restaurants will have tents set up for extra socially distanced seating and some outdoor music locations will be repositioned to allow for more social distancing.


For those not ready to shop in person you can also shop our stores online by clicking here or buy local restaurant gift cards by clicking here.


A very special thank you to our premier sponsor the City of Annapolis and the State of Maryland for their strong support! Also thank you to our media sponsors What's Up Magazine and Eye on Annapolis for their support. 


Some of our Featured Attractions:

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

  • Snowflake Alley: A magical passageway on Main Street that helps you begin your journey towards State Circle and Maryland Ave. (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.

  • Visit the Alpacas on the top of Main Street. 

  • 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:

  • Main Street and Maryland Ave will be pedestrian-only.

  • Free parking is available at most parking garages during Midnight madness including Knighton Parking Garage, Gotts Court Parking Garage, and Hillman Parking Garage from 4 pm to midnight and the Calvert Street Parking Garage from 6 pm to 6 am.

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

  • Parking Meters will be free for short term parking. Use the Code ParkDTA on Parkmobile App and one hour bonus time at parking meters.

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