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The Best Ways To Celebrate the Holiday Season in Annapolis

November 9, 2023

The holiday season is here, and everyone at Ginger Cove is ready to celebrate. While there are plenty of holiday events happening in our community, there’s also a full schedule of festive events in Annapolis. Take a look at all that’s going on in our city to usher in the holiday season with cheer and excitement.

There are so many things to enjoy in Annapolis year-round, especially during the winter holidays. If you’re visiting your loved one at Ginger Cove this season, be sure to explore the holiday events at both Ginger Cove and in the wider community for a spirited season.

Celebrate the Holiday Season in Annapolis 

Annual Tree Lighting on November 17

The Annual Tree Lighting at the Annapolis Town Center will start at 7 p.m. With fireworks, a DJ, and a visit from Santa at 7:45 for the tree lighting, this event is sure to be full of festive cheer.

If you’re one of the first 500 families to visit the Town Center, you’ll get a First Annual Annapolis Town Center ornament.

Lights on the Bay on November 19

Starting on Sunday, November 19, 2023, and continuing until Monday, January 1, 2024, you can drive through Sandy Point State Park for Lights on the Bay, a dazzling collection of light displays.

With displays of colonial Annapolis, the North Pole, a sixteen-foot teddy bear on the Chesapeake Bay, and the Thomas Point Shoal Lighthouse, this is a great way to enjoy the holiday lights in the warmth of your own vehicle.

Grand Illumination of the Annapolis Tree on November 26

The Sunday after Thanksgiving, you can jump right into the spirit of the season at the Grand Illumination of the Annapolis Tree. The event will take place near the Market House from 4 – 7 p.m.

Enjoy Christmas carolers, music, delicious hot cocoa, and crafts for kids to create something fun.

Annapolis Chocolate Binge Festival on December 3

Calling all chocolate lovers!  Be sure to mark your calendars on Sunday, December 3, from 11 a.m. – 5 p.m. to visit the first block of West Street for the Annapolis Chocolate Binge Festival. With multiple vendors selling all kinds of chocolate and other treats, this is the event for anyone with a sweet tooth.

There will be a Chocolate Gingerbread Decorating Contest, the West Street Holiday Light Canopy, live music, and Santa.

Annapolis Holiday Market on December 7, 8, 9, and 10

This open-air market will showcase artisans from the Annapolis area starting Thursday, December 7, from 4 – 10 p.m. Located along the city dock, this waterfront market will have everything from handcrafted goods, delicious food, and plenty of fun things to do. Take a ride on the Jolly Express Cruise, stroll around the Annapolis Holiday Market, and enjoy everything that historic Annapolis has to offer.

Midnight Madness on December 7, 14, and 21

Of all the events in Annapolis during the holidays, this is a can’t-miss. Midnight Madness fully embraces the holiday hustle and bustle, with stores on Main Street, Maryland Avenue, and West Street, staying open from 4 p.m. until midnight on Thursdays, December 7 and 14, and from 4 – 11 p.m. on Thursday, December 21.

This is a perfect time to get ahead of Christmas shopping as stores offer discounts and sales, or to get out and be  part of the crowd and enjoy the holiday displays and treats.

Eastport Yacht Club Lights Parade on December 9

Celebrating its 41st year of this delightful event, the Eastport Yacht Club Lights Parade will be held on Saturday, December 9, from 6 – 8 p.m. Be sure to watch the parade of boats illuminated in twinkling holiday lights as they float through the Annapolis Harbor and Spa Creek. This festival of lights on the water is a fun holiday tradition in Annapolis and is sure to be a great experience for the whole family.

Experience the Festivities at Ginger Cove 

Residents at Ginger Cove have so much to look forward to in their community during the holiday season. Some of our residents’ favorite traditions include Breakfast With Santa, the Grand Tree Illumination, Community Caroling, and the Holiday Gala With Fine Dining and Entertainment.

All the festivities lead to the annual Christmas Eve tradition of champagne and treats with friends by the fireplace to welcome a merry Christmas to all at the community.

With so much to do in Annapolis, and at Ginger Cove, your holidays are certain to be merry and bright. If you’d like to learn more about life in our community, give us a call at 410-670-7793 and schedule a tour.


Come be our guest. Take a tour. Ask questions. It’s the best way to decide to be here all the time. Call 410-266-7300 to schedule a tour of our community.

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