December 6, 2023
Annapolis, US 42 F

Holiday events around Annapolis

The City of Annapolis is always an exciting place during the winter holiday season and 2019 is no exception. Here are some of the events and activities happening around the City in the month of December.

Holiday Open House at City Hall – Dec. 5 at 4:30 p.m. to 6:30 p.m.

A Holiday Open House in Council Chambers at City Hall, 160 Duke of Gloucester. “Julie and I invite you to come to City Hall to share holiday refreshments with us before Midnight Madness shopping in downtown Annapolis,” Mayor Buckley said. “This is a time for us to share with you to joy of the holiday season!” The City will be accepting donations of hats, gloves and scarves for the Lighthouse Shelter.

Midnight Madness – Dec. 5, 12 and 19 from 6 p.m. to midnight

Midnight Madness takes place in downtown with stores staying open late, giving locals and visitors a chance to shop local. A highlight every year are the Alpacas on Main Street. Word has it that there is a baby alpaca this year! Make a dinner reservation and bring your holiday shopping lists. Park at Park Place or Knighton Garage for $5 for the night (prepaid at and take the Circulator. Download the circulator app to track it on your smartphone. It will be running every seven minutes to get you from one favorite store to another up and down Main and West Streets and Maryland Avenue.

Winterfest – Dec. 7-8 and 14-15 from noon to 6 p.m.

Winterfest and European Market on Giddings Avenue in West Annapolis, a holiday market with glowing lights, beautiful trees, skilled artists and crafters, food and mulled wine, Stella, champagne, cocktails and hot chocolate. Bring the entire family for activities and fun!

Chocolate Binge Festival – Dec. 8 from noon to 5 p.m.

The Fifth Annual Annapolis Chocolate Binge Festival in the Arts District on the first block of West Street. It costs $5 where you can indulge your sweet tooth with more than 40 chocolate vendors selling specialties including chocolates, caramels, bars, fudge, cookies, cakes martinis macaroons, cupcakes, pies, brownies and more. Take time to make S’mores at the fire pit in the middle of West Street with the Annapolis Fire Department, enjoy Hot Coco with the Popo courtesy of the Annapolis Police. Take a jump in the giant gingerbread house moon bounce. As night falls, look up! The holiday street light canopy will be lit. Live music and entertainment awaits.

Eastport Yacht Club Lights Parade – Dec. 14 starting at 6 p.m.

The Eastport Yacht Club Lights Parade is a beloved Annapolis holiday tradition. Every year on the second Saturday in December magic happens in the Annapolis Harbor as boats suddenly appear out of the cold winter night illuminated with lights and crewed by jolly revelers! Pick your vantage point overlooking Spa Creek.

Miracle on Annapolis Street – Dec. 26 from 11 a.m. to 5 p.m.

Come down and see the Budweiser Clydesdales for the Miracle on Annapolis Street. There will be food trucks, vendors, games and activities for adults and children.

Military Bowl Parade and Game – Dec. 27 starting at 9 a.m. (parade) and noon (game)

The next day, the Clydesdales kick off the fun at 9 a.m. at City Dock, with a parade to Navy-Marine Corps Memorial Stadium. Kickoff for the Military Bowl starts at noon

New Year’s Celebration – Dec. 31 starting at 3 p.m. (family celebration at Bates) and 8 p.m. (City Dock)

Join Mayor Gavin Buckley and his family for the 2020 Annapolis New Year’s Celebration on December 31. There will be two sets of fireworks to fit everyone’s schedules. The early family-friendly fireworks experience will be behind Maryland Hall at the Bates Athletic Complex around 5:15 with festivities for kids and families getting underway around 3 in the afternoon. There will be live music and free crafts plus fun with the Annapolis Police and Fire Departments! Downtown fireworks will go off at midnight, with DJ starting at 8 p.m. and a live dance band from 9 p.m. to midnight. The Mayor will count down to 2020 with residents leading to the grand fireworks finale. The City Dock New Year’s eve is an alcohol-free event, visit one of our wonderful local bars or restaurants or hotels if you want to celebrate with alcohol, but please drink responsibly and utilize designated drivers to ring in the New Year!

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