Annapolis, Maryland is one of the most charming towns in the country to visit throughout the year. But, there is something extra magical about the holidays in this city. Located on the Chesapeake Bay, this town comes alive with mesmerizing Christmas light displays, the Annapolis Christmas Tree, storefronts decked to the nines, and, of course, the Annapolis Holiday Market. Taking place this year from Thursday, December 7 to Sunday, December 10, 2023, the Annapolis Holiday Market is one event that will make even Scrooge himself smile.

Mark your calendars for the return of the Annapolis Holiday Market at the City Dock in downtown Annapolis. This market is not only full of vendors but holiday magic as well.

In 2022, this outdoor holiday market left an impression as 45 artisans offered their unique products. But this year, it is bigger than ever with more than 100 artisans and specialty food vendors. It’s the place to find the perfect Christmas gift for everyone on your list ... and some tasty treats as well.

As you browse the market, you’ll find all types of handcrafted goods from home décor and candles to handbags, photography, pottery, jewelry, and so much more.

And to make your holiday shopping experience that much better, the Annapolis Holiday Market will offer hot chocolate, apple cider, wines, and specialty holiday liquors that you can enjoy as you shop.

In addition to the incredible vendors, you'll have a full experience with entertainment, visits from Santa, and photo ops. For example, you can capture a photo under the holiday market entrance archway when you arrive. It’s a tradition you’ll look forward to year after year.

Admission is free to this Maryland market and don't worry about parking. There are several free and discounted parking locations in the area.

A few parking options include the Calvert Street Parking Garage (19 St. Johns Street) and the Whitmore Parking Garage (25 Clay Street). Parking spaces on commercial streets are free for two hours when you use the Parkmobile app. Free shuttles also run from the West Street area parking garages and hotels to the City Dock area.

Keep in mind this is not a small holiday market. In 2022, more than 25,000 visitors attended the event and this year, you can expect even more. But if you want to avoid the large crowds, it is recommended to attend on Friday, December 8.

The Annapolis Holiday Market is just one of the many events we recommend you check out during this weekend in December. Another jolly event that will fill you with cheer is Midnight Madness. Together, with the Annapolis Holiday Market, they create one of the biggest holiday weekends in the mid-Atlantic.

Midnight Madness is a downtown-wide holiday event that takes place Thursday evening. During this highly-anticipated event, approximately 90 stores will stay open until midnight, allowing you to shop until you can’t keep your eyes open anymore. There will also be sales, refreshments, carolers, entertainment, and more for you to enjoy.

Lastly, if you're looking for even more holiday magic, don't forget to check out the beloved Eastport Yacht Club Lights Parade, which takes place at the same time as the market.

The Annapolis Holiday Market is one of the best ways to fill you with Christmas magic — and to finish your holiday shopping. It’s a tradition that will certainly make you holly, jolly, and merry.

For more information on this Maryland event, make sure to visit the Annapolis Holiday Market website. Don’t forget to follow the Annapolis Holiday Market Facebook page for current updates and news as well.

Have you ever attended this holiday market in Maryland? What are some of your favorite traditions in the state? Let us and your fellow Christmas lovers know in the comments.