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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 Boat Show | April 12 to 14

Climb aboard a wide array of powerboats of every style and size – from fishing boats and trawlers to pontoon boats and luxury cruisers. With plenty of on-site parking available, food and beer stations, and live entertainment, the Bay Bridge Boat Show is guaranteed to be a great day on the Bay.

Spring Sailboat Show 2024 | April 26 to 28

Set in the seaport of Annapolis, it displays catamarans, monohulls, racing boats, and inflatables – with over 100 new and brokerage yachts. Check out the vessels and spend some time shopping for the latest equipment, including electronics, clothing, and other accessories..

Visit Annapolis & Anne Arundel County Santa Maria Cup | April 30 to May 4

Annapolis, known worldwide as America’s Sailing Capital, returns to its nautical roots with the return of Women’s Match Racing with the Visit Annapolis & Anne Arundel County Santa Maria Cup, supported by the Maryland Sports Commission.

Mother's Day and St John's Commencement Week | May 1

St. John’s Commencement Week is an exciting and memorable celebration of academic achievement and personal milestones. During this week-long event, graduating students at St. John’s University come together with their families and friends to mark the culmination of their educational journey.

Commissioning Week | May 19 to 26

The United States Naval Academy Commissioning Week is a celebration for Midshipmen, their families, and the entire town of Annapolis. Woven into the fabric of our historic city, visitors come from all over to celebrate this special honor with graduating Midshipmen.

Plein Air Annapolis | June 2 to 9

Plein Air Annapolis is a vibrant celebration of art and the great outdoors, where talented artists gather to paint en plein air, capturing the picturesque landscapes and historic charm of Annapolis, Maryland. This annual event brings together a community of artists, art enthusiasts, and nature lovers for a week filled with creativity and inspiration.

Annapolis Pride | June 1

Anyone who has attended the Annapolis Pride Parade & Festival knows there is no happier occasion. Everyone is smiling, laughing, and waving, usually while decked out in the most boisterous garb— from feather boas, rainbow capes, and tutus to the most magnificent drag queens.

Induction Day at the Academy | June 27

Induction Day at the Academy is a momentous occasion that marks the beginning of an exciting journey for new cadets. Held with great ceremony and tradition, this day symbolizes the transition from civilian life to military training.

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Annapolis Crab Feast | August 2

The Annapolis Crab Feast is a quintessential Maryland culinary experience that brings together seafood lovers from all around. This iconic event features piles of steaming, succulent blue crabs seasoned with Old Bay spice, served alongside classic sides like corn on the cob and coleslaw.

Annapolis Songwriters Festival | September 14 to 17

Blondie and LeAnn Rimes will headline this year’s festival! The Annapolis Songwriters Festival is modeled after the hugely successful Key West Songwriters Festival, which in its 26th year, continues to be the largest festival of its kind in the world.

Maryland Seafood Festival | September 14 to 15

The Maryland Seafood Festival has been gracing the shores of the Chesapeake Bay since 1966 with delectable crab, oysters, shrimp, mussels, and locally caught fish prepared any way you like it! Come for the food, and stay for the views!

Maryland Renaissance Festival | August through September

Beginning in August and lasting through the end of October, Lords, and Ladies from faraway lands gather to experience one of Maryland’s most extravagant events.

Powerboat Show 2024 | October 3 to 6

The United States Powerboat Show features everything from luxurious motor yachts to trawlers, high-performance boats, and offshore fishing vessels.

Sailboat Show 2024 | October 10 to 14

The United States Naval Academy Commissioning Week is a celebration for Midshipmen, their families, and the entire town of Annapolis. Woven into the fabric of our historic city, visitors come from all over to celebrate this special honor with graduating Midshipmen.

Kunta Kinte Heritage Festival | TBA (October)

In September 1987, the Kunta Kinte Celebration was born in Annapolis, Maryland. Now known as the Kunta Kinte Heritage Festival, the festival celebrates the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent.

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.