Seasonal & Holidays
Midnight Madness Returns To Annapolis For Late-Night Holiday Shopping
Midnight Madness is back. The late-night shopping event brings holiday festivities to downtown Annapolis. See the schedule.

ANNAPOLIS, MD — Midnight Madness is back again in downtown Annapolis, bringing late-night shopping and holiday festivities to roughly 170 businesses in the city's historic district.
The annual event runs on the first three Thursdays of December. This year, that's Dec. 4, 11 and 18. The first two dates, stores and restaurants stay open until midnight. Businesses remain open until 11 p.m. on the final date.
"This is the evening you will find many of your friends and neighbors all enjoying the festive atmosphere along Main Street, Maryland Avenue, West Street, and the City Dock area," Erik Evans, executive director of the Downtown Annapolis Partnership, said in a press release. "Downtown Annapolis is a vibrant holiday destination for generations of locals and visitors."
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About 90 stores and 80 restaurants in downtown Annapolis are participating.
The first night, Mayor Jared Littmann is hosting an open house at 4:30 p.m. at Annapolis City Hall.
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The second night will feature the West Street Holiday Market on the first block of West Street.
The third night brings the Annapolis Holiday Market to the front lawn of St John's College.
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New businesses this year on Main Street include: Abby Adams Boutique, Pepper Palace, Capo Deli, Local Coast and Made+.
Maine Cottage also debuted this year on Conduit Street, and Stardust Deluxe Boutique opened on Maryland Avenue.
HERE. a popup-shop is located on Fleet Street this holiday season.
Businesses remain open on Dock Street during the construction of City Dock Park.
Many shops will have sales and offer refreshments to shoppers. There will also be performances, and live alpacas have previously made an appearance at Alpaca International on Main Street.
For the first time, Santa will be in front of the Blanca Flor Silver Jewelry store on Market Space every Thursday evening starting at 6:30 p.m.
Downtown Annapolis will be filled with decorations sponsored by Sheehy Lexus of Annapolis. Snowflake Alley, sponsored by RBC Wealth Management, is always a solid photo opportunity on Main Street. There will also be light canopies over Maryland Avenue and West Street, and a 25-foot live Christmas tree on Market Space.
"Midnight Madness combined with the holiday decorations and all the other downtown holiday events including the Eastport Yacht Club’s Lights Parade, Santa Speedo Run, Annapolis Holiday Market, a [Kwanzaa] Celebration, Handel's Mesiah concerts, A Christmas Carol, and the Menorah Parade and Lighting all are part of why Annapolis is regularly ranked as a top holiday destination," Evans said in the release.
The Downtown Annapolis Partnership offered these tips for parking:
Parking in garages is recommended to avoid the 2-hour time limits for on-street parking. This will allow you to relax, stay late, and enjoy all the festivities, shopping, and dining. Parking is always free on weekday evenings starting at 6 pm at the State-owned Calvert Street Parking Garage (19 St. Johns Street). The county-owned Whitmore Parking Garage (25 Clay Street) always has a flat rate starting at 4 pm of $2. The free City Annapolis Current Trolley, which is an electric shuttle cart, will be picking people up from both of these parking garages during Midnight Madness.
The City of Annapolis is offering, during the holiday season, the first hour free in the Mills-Hillman Parking Garage (150 Gorman Street) when you use the Park Mobile App, and 2 hours free parking on commercial streets when you use the ParkMobile parking apps. The city-owned Park Place Parking Garage is offering a $5 flat rate parking special during Midnight Madness nights. Shoppers can also ride the free Circulator Bus, which picks up from the Knighton (1A Colonial Ave) and Park Place (1 Park Place) parking garages along West Street. City of Annapolis residents are also reminded that they can apply for free 2-hour daily parking benefits, if they have not already done so, that can be used at city-owned parking garages year-round.
More information is available at midnightmadnessannapolis.com.
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