By Erik Evans

The Most Festive Time to Shop for the Holidays

The biggest and best nights of the year to shop in downtown Annapolis are on the first three Thursdays in December during Midnight Madness. This annual three-day event is presented by the Downtown Annapolis Partnership to encourage locals to visit their favorite shops and restaurants downtown.  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.

The downtown Annapolis area will be filled with traditional holiday decorations sponsored by Sheehy Lexus of Annapolis. The fun Snowflake Alley sponsored by RBC Wealth Management on Main Street is always a popular destination for picture taking. You will also find beautiful storefront windows, decorated buildings, garland, wreaths, light canopies over Maryland Avenue and West Street, and a large real Christmas tree near the Market House. Many of these designations are popular places for picture taking. A new public art installation of artistic streetlights has just been installed by the Downtown Annapolis Partnership in time for Midnight Madness in Weisman Park near the Visitors Center which will be fun to photograph.

As you stroll the streets to shop and dine during Midnight Madness you will find performances around every street corner including choirs, carolers, steel drums, dancers, bands, alpacas, and a holiday movie. This event combined with the holiday decorations and other events including the Eastport Yacht Club’s Lights Parade on the 14th, Santa Speedo Run, Annapolis Holiday Market, a Kawanza Celebration, and the Menorah Parade and Lighting all are part of why Annapolis is regularly ranked as a top holiday destination.

The Midnight Madness shopping nights are December 5th, and 12th, when stores and restaurants stay open until Midnight, and on December 19th, the Eleventh Hour when they stay open until 11 pm.

There are about 90 stores and 80 restaurants in downtown Annapolis participating.  During the first Midnight Madness, you can also attend the mayor’s open house at 5 pm at City Hall and on the second night, you can also attend the opening night of the Annapolis Holiday Market from 4 pm to 10 pm on the City Dock.  Alongside your favorite long-time businesses there are several new businesses this year on West Street, Maryland Ave, Market Space, and Main Street. Most of the businesses downtown are locally owned and some offer locally made items for sale. Many of the shops will offer special sales, exclusive items, and refreshments as you shop. The historic downtown area provides a unique old-fashioned shopping experience where customer service is still in vogue. Shoppers are encouraged to arrive early for happy hour and dinner before the evening shopping gets in full swing.

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 Calvert Street Parking Garage (19 St. Johns Street). Whitmore Parking Garage (25 Clay Street) always has a flat rate starting after 4 pm of $4. The City of Annapolis is offering during the holiday season the first hour free in Hillman Parking Garage (150 Gorman Street) and 2 hours free parking on commercial streets when you use either the Premium or ParkMobile parking apps. Shoppers can also ride the free Circulator which picks up from the Knighton (1A Colonial Ave) and Park Place (1 Park Place) parking garages along West Street.

For additional information on Midnight Madness, lodging, shopping, restaurants, sponsors, gift cards, and more visit www.midnightmadnessannapolis.com.