Midnight Madness

A Festive Shopping Time in Downtown Annapolis 

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

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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.  Those who arrive early may enjoy Happy Hour specials at select restaurants. 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 Towns in the nation. Bring your friends and family to 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.

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Make it extra special by booking a holiday party at one of the many downtown Annapolis restaurants.

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You can also shop at many of the stores and restaurants online in downtown Annapolis. 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, WRNR Radio and Eye on Annapolis. Thank you to 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 & 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!

• Beautiful storefront window displays.

• During the third Midnight Madness, you can also visit the Annapolis Holiday Market at St John's College.

• During the second and third Midnight Maddness, you can also visit the West Street Holiday Market.

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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

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

• City residents can park at the City-owned parking garages for free for 2 hours at Hillman Garage. Contact Annapolis Parking at 60 West Street for details.

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

• $5 flat rate parking at Park Place Parking Garage on Midnight Madness nights. Plus, a free shuttle to take you downtown.

• The first hour of parking is free at the Mills-Hillman Parking Garage when you use the Park Mobile app.

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

• Learn more about parking specials and free shuttles by clicking here.