Check Availability

Events in Annapolis, MD

Each season brings forth new events in Annapolis, MD. Attend prestigious regattas, famed matches between the Naval Academy and St. John’s College, or maritime festivals by the Chesapeake Bay. These events are all held annually are a great opportunity to visit Annapolis. There is never a shortage of exciting things to do in our beautiful and historic city.

Read more about annual events here. | See the latest Navy Sport’s calendar!

2024 Local Events

Bay Bridge Run | November 10

The Bay Bridge Run, organized by Corrigan Sports, is a unique opportunity to run or walk across the Chesapeake Bay Bridge. This 10K course starts in Anne Arundel County and ends on Kent Island in Queen Anne’s County. After the race, enjoy a post-race party with food, music, and camaraderie.

Lights on the Bay | November 19 - January 1

Lights on the Bay is an annual holiday light display at Sandy Point State Park in Maryland, featuring over 60 animated and stationary exhibits along a scenic two-mile drive. It’s a festive tradition for families and visitors to enjoy from late November through the holiday season.

Grand Illumination | December 1

Kickoff the holiday season at the Annapolis City Dock! The Grand Illumination event will feature music and dance performances, a visit from Santa, and, of course, the lighting of Annapolis’ largest tree yet.

Chocolate Binge Festival | December 1

The Annapolis Chocolate Binge Festival is a sweet celebration of all things chocolate, featuring local vendors, live music, and family-friendly activities, including its third annual gingerbread house decorating contest. Held annually in downtown Annapolis, it’s the perfect event for chocolate lovers looking to indulge in a variety of treats.

Midnight Madness Holiday Shopping | December 5, 12, 19

Midnight Madness in downtown Annapolis is a festive holiday shopping event where stores stay open until midnight on select December nights. Shoppers can enjoy holiday decorations, carolers, and special deals while exploring local boutiques and restaurants.

Eastport Yacht Club Lights Parade | December 14

The Eastport Yacht Club Lights Parade is a festive annual event in Annapolis, where brightly decorated boats sail through the Annapolis Harbor and Spa Creek. This holiday tradition offers a spectacular display of creativity and lights for spectators along the waterfront.

Banneker-Douglass Museum Kwanzaa Event | December 14

The Banneker-Douglass Museum in Annapolis hosts an annual Kwanzaa event that celebrates African American culture and heritage through educational activities, performances, and communal gatherings. This vibrant celebration typically features traditional music, dance, and workshops, fostering a spirit of unity and reflection on the principles of Kwanzaa.

Military Bowl | December 28

Hosted at Navy-Marine Corps Memorial Stadium, the Military Bowl, brings together teams from top conferences, such as the ACC and the American Athletic Conference. The game is accompanied by a patriotic atmosphere, including a parade through downtown Annapolis featuring military bands, vehicles, and fanfare that honors servicemen and women while showcasing exciting football action in a historic setting.

New Years Eve Annapolis Yacht Party | December 31

The New Year’s Eve Annapolis Yacht Party offers a unique and luxurious way to ring in the new year. Set against the stunning backdrop of the Chesapeake Bay, guests can enjoy an elegant evening filled with gourmet dining, live entertainment, and breathtaking views of the fireworks over the water. This exclusive event promises a festive atmosphere with dancing and celebration, making it an unforgettable way to welcome the new year with friends and fellow revelers.

We look forward to welcoming you to our historic Bed & Breakfast where you can experience the events of the city that we are so proud to call home. Make sure to check the Annapolis Events Calendar for all the fun and exciting events in Annapolis, MD.