How to Get the Best From Annapolis’ Midnight Madness

Midnight Madness is the official start of the holiday season for Annapolis peeps. It’s a big event and huge fun.


First two Thursdays of December – Dec. 2 & 9, 4pm to 12am

Third Thursday of December – Dec. 16, 4pm to 11pm

Historic, colonial downtown Annapolis goes full Charles Dickens. Christmas decorations fill Main Street, holiday carolers and musicians fan out with holiday cheer, creating a downtown Winter Wonderland.

Even if you don’t personally celebrate Christmas, it’s a great immersion into a happy event. Retailers will have gifts for the multiple religious celebrations during this season.

Shops re-set for the event starting at 4pm and stay open until 12am. Many shops have holiday treats and beverages available for shoppers.

The event encompasses the entire downtown and goes up the hill to West Street and Maryland Avenue, as well across Spa Creek in Eastport.

It’s practically impossible to do the entire event in one night. Annapolitans make it a weekly holiday event to meet friends, shop and dine.

An Insider’s Guide to Midnight Madness in Annapolis

FUN PART #1 – Shopping

There’s a theme to shopping in Annapolis based on location. It evolved over years unintentionally. There are exceptions to the rule, but generally it’s:

Main Street – chic clothing boutiques, tourist & gift shops, shops targeting Naval Academy visitors with maritime themes, pop-up stores

West Street – art galleries, pop-up stores

Maryland Avenue – antique stores, vintage & new trendy clothing, household gifts, hipster wine/liquor store and pop-up stores

State Circle – jewelry stores, pottery store

Dock Street / Harbor Area – jewelry stores, gift shops, boating gear, wine/liquor store

Here’s a list of participating stores, boutique and galleries in Downtown Annapolis

Participating merchants may offer complimentary refreshments (sometimes they’re the adult version), as well as specials and shopping incentives.

FUN PART #2 – Entertainment

The historic streets are filled with music, even in the snow. The town brings in carolers, Choirs, musicians and street performers.

Some set up on a street corner. Others walk about the downtown area doing impromptu performances.

Even the shops step it up. Alpaca International, which sells high-end, imported wool clothing, brings live alpacas to Annapolis’ Main Street. They’re in a manger-like stall outside the store. Kids love ’em.

FUN PART #3 – Colonial Bars & Restaurants

Reynolds Tavern, Annapolis
The upstairs restaurant at Reynolds Tavern. The second floor is a B&B, and in the basement (former kitchen) is the pub.

Nothing says Charles Dickens Christmas like a warm drink, or a beer, in a Colonial tavern. Annapolis has a lot of them.

1747 Pub at Reynolds Tavern, Annapolis
1747 Pub in the basement of Reynolds Tavern. This is the former kitchen of the historic colonial home. Live music is tucked into the corner on weekends. (photo courtesy Reynolds Tavern)

Here’s the inside scoop:

They are small and can be tight. If you don’t want that, Reynolds Tavern on Church Circle has a beer garden that they open during Midnight Madness for Christmas movies on a big screen.

Galway Bay on Maryland Avenue is a must stop for many locals because the Irish coffee is off-the-charts. The Irish bar is also know for it’s special egg nog. They have outside tastings for adults.

The Maryland Inn at the top of Main Street is a great half-way warm-up stop during a cold night.

At the bottom of Main Street near the water is Middleton’s Tavern and McGarveys Saloon. They offer fresh Chesapeake Bay oysters and oyster shooters, a fun way to start the evening.

Restaurants all over the area will be offering special deals. They will be busy, so please be patient as they work on seating you.

Here’s a list of Downtown Annapolis Restaurants and what they serve.


Chancery Lane in Annapolis
Chancery Lane is one of Annapolis’ pedestrian alleys. It’s a shortcut from Main Street to the state capitol.

Annapolis has a number of shortcuts through the colonial downtown buildings to get to other sections of the downtown area. They’re called alleys, but they’re just short walkways.

Cabbage Alley turns into “Snowflake Alley” during the Christmas season. It’s lit up with large snowflakes and is a popular photo opportunity, as well as shortcut between Main Street to State Circle and Maryland Avenue.


Parking can be tricky. There’s not much room in downtown Annapolis.

  • 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.

Don’t count on Annapolis to be generous and not ticket during Christmas season. They want to circulate shoppers through so watch your meter time and don’t park where the curb is painted red. Pull in your rear view mirror when parked on those narrow streets.

Wear comfy shoes, you’ll be walking a bit. The distance from the free garage to the bottom of Main Street is just under a mile.

Take a deep breath as you turn to drive into Annapolis, then exhale. Let it go. You’re about to be enveloped by the Holiday Spirit.

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