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Date(s) - December 15, 2022
4:00 pm - 11:45 pm


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, Market Space 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 throughout the downtown area.

You can also shop many of the stores and restaurants in downtown Annapolis online  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: Sheehy Lexus of Annapolis  and the City of Annapolis for their strong support! Thank you to our media sponsors What’s Up Magazine and Eye on Annapolis. Thank you to South Annapolis Yacht Center 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 Holiday 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 downtown parking experience more enjoyable:

  • Free parking is available at Calvert Street Parking Garage (19 St Johns Street) 6pm to 6am

  • $2 parking is available from 4 pm to 6am at Whitmore Parking Garage (25 Clay Street).

  • $5 parking is available at Knighton Parking Garage and Park Place Parking Garage.

  • Parking Meters will be free for short-term 2 hour parking. Use the Code ParkDTA on Parkmobile App and get an additional one hour bonus time at parking meters.

  • Free Circulator buses run along West Street, Calvert Street, State Circle, and Main Street and will pick you up and bring you back to any downtown Annapolis Parking garage.