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Midnight Madness is Sponsored by
Christmas Tree is Sponsored by
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, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland and free on-the-street entertainment.


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.  The streets will be filled with entertainment and holiday decorations, and the shops will have refreshments and sales. It is the perfect opportunity to get your holiday shopping done and see why Annapolis is ranked as one of the Top Christmas Toowns in the nation. Bring your friends and family and enjoy the holiday season together. When we shop locally, 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 at 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 Annapolis Art in Public Places Commission 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 the Featured Downtown 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!

  • During the first Midnight Madness, you can also visit the new Annapolis Holiday Market on the City Dock.

To make your downtown parking experience more enjoyable:

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

  • The first hour in Hillman Parking Garage will be free when you use the   Parkmobile App

  • Parking on commercial streets will be free for short-term 2-hour parking when you use the Parkmobile App.

  • City residents can park at the City-owned parking garages for free for 2 hours at Hillman Garage with a promo code from Premium Parking or Gotts, Knighton, and Parking Place garages with parking passes from 60 West Street.

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

  • Free Circulator buses and shuttles will help you get around town with stops at many of the parking garages.

  • Learn more about parking and free shuttles at

Annapolis Art in Public Places Commission &
Diehl's Produce

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