Spend Christmas At This Charming Eastern US Coastal Destination

Although there are magical Christmas towns and villages all over the world, most of them are located throughout Europe. However, here in the United States, you can find holiday magic in Annapolis. Located less than an hour from Baltimore, on the Chesapeake Bay, Annapolis is the capital of Maryland. The historic waterfront city is home to the United States Naval Academy and is known as the "Sailing Capital of the U.S." Notably, the city has colonial architecture and European-style brick-paved streets. And when the holidays come around, Annapolis goes big.

Bloggers and visitors often name Annapolis one of the country's top places to experience a picture-perfect Christmas. Every year since 1913 (via The Baltimore Banner), the city has put up a massive Christmas tree in the downtown area and has a public lighting ceremony. Moreover, the city's buildings, streets, and boats are generously decked out with lights and holiday decor. 

While it rarely snows during Christmastime in Annapolis, seasonal activities bring joy to all. From the end of November to the end of December, Annapolis' calendar of events is filled with things for locals and tourists to enjoy, including productions of "The Nutcracker" and the Santa-Speedo-Run. Moreover, the city has countless unique holiday festivals and attractions. 

One-of-a-kind Holiday events in Annapolis

There's so much to do during the holidays in Annapolis, there really is something for everyone in the family to relish. In 2022, the city introduced the Annapolis Holiday Market in the Downtown area, a free event featuring live entertainment (including the opportunity to interact with Santa Claus), food, and locally-made gifts. In 2023, the Annapolis Holiday Market will only be open from December 7 to 10.

Love chocolate or sweets? Then, the Chocolate Binge Festival, celebrated Downtown, is for you. You can eat and shop for chocolate, look at gingerbread houses, enjoy live holiday music, and more. This is a one-day event; in 2023, it will be held on December 3. Admission is $5.

For those who can't get enough holiday shopping or want to support small businesses, there's the annual tradition of Midnight Madness. On select days in December, certain shops in Downtown Annapolis stay open until midnight. Carolers, live music, and plenty of holiday decor and cheer make this an unforgettable experience.

Check out Lights on the Bay at Annapolis' Sandy Point State Park for even more Christmas lights. This event lasts from the end of November into the New Year and is a drive-through Christmas light display. Admission is $20 per car. In addition, every second Saturday in December, the Eastport Yacht Club hosts a light parade in Annapolis Harbor featuring elaborately decorated vessels.

Accommodation options in Annapolis

Annapolis, especially during the holiday, is an excellent getaway for anyone living in major cities on the East Coast. For example, the city is about four hours away from New York City, two and a half hours from Philadelphia, and 45 minutes from Washington, D.C.. But for those who don't live on the East Coast and need to fly in, Annapolis does not have an airport. Travelers can land at Baltimore-Washington International Thurgood Marshall Airport (BWI) or Ronald Reagan Washington National Airport (DCA), under an hour's drive from Annapolis.

You'll want to stay downtown for all of the holiday happenings. Thankfully, Annapolis has many inns and bed & breakfasts that will make your holiday vacation even more dreamy. Within walking distance from the Annapolis Holiday Market is the Flag House Inn. The inn dates back to 1879, but its chic rooms have modern elements. Free parking and breakfast are included with your stay.

A more affordable option Downtown is The Maryland Inn (pictured). The stunning historic brick building was built in the 1770s, and while it has no fancy amenities, the rooms are elegantly decorated. Alternatively, you can book an Airbnb. While the downtown area is expensive, more affordable apartments can still be found.

For a warm meal, head to Cafe Normandie. The French eatery is decorated for the holidays and has a picturesque ambiance that will keep guests snug through the cold.