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Midnight Madness is Sponsored by
Christmas Tree is Sponsored by
U.S. Naval Academy Alumni Foundation
Diehl's Produce
Snowflake Alley is Sponsored by
RBC Wealth Management 

Midnight Madness

A Festive Shopping time in Downtown Annapolis 

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 and restaurants are at 25% capacity. We also ask everyone to wear a facemask while downtown, to bring hand sanitizer so you can wash your hands frequently and stay home if you are sick. This year there will not be live music, entertainment or refreshments while shopping. The goal is to remove the party atmosphere and still safely support our local businesses by shopping locally.

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.

Many stores will also be staying open late on other evenings until 9 pm in December, especially on Fridays and Saturdays to give you additional options. Some stores are also offering curbside pick up and shopping by appointment, Look for the Open Late Flags in December.


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 sponsors: the City of Annapolis, Sheehy Lexus of Annapolis, and the State of Maryland for their strong support! Thank you to our media sponsors What's Up Magazine and Eye on Annapolis. Thank you to the U.S.Naval Academy Alumni Foundation and Diehl's Produce for sponsoring this year's Christmas tree and to RBC Wealth Management for sponsoring Snowflake Alley, You are all great partners in making downtown Annapolis even better.


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:

  • 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.