Top 10 Things to Do in Annapolis, Maryland

Maryland’s capital city welcomes you with open arms and a host of possibilities!

View of Annapolis from Spa Creek
Annapolis is world renowned as America’s Sailing Capital and one of the top waterfront destinations in the United States. (Photo credit: Sean Pavone)
Noon formation at the US Naval Academy
Be sure to catch noon formation at the US Naval Academy.
Maryland State House in Annapolis
The Maryland State House is the oldest state house in continuous legislative use in the nation.
Sail boats in Annapolis, Maryland
Annapolis is surrounded by the Chesapeake Bay, four rivers and more than 400 miles of shoreline.
Cantler's Steamed Crabs
Treat yourself to the famous Chesapeake Bay seafood of Annapolis.
William Paca House and Gardens
Tour the house and garden of Declaration of Independence signer William Paca.
View of Annapolis from Spa Creek
Noon formation at the US Naval Academy
Maryland State House in Annapolis
Sail boats in Annapolis, Maryland
Cantler's Steamed Crabs
William Paca House and Gardens

Located just 32 miles from Washington, DC, 26 miles from Baltimore and minutes from BWI Thurgood Marshall Airport, Annapolis is the gateway to North America’s largest estuary, the Chesapeake Bay. A bustling port town in the 18th century, this National Historic Landmark is world renowned as America’s Sailing Capital and one of the top waterfront destinations in the United States.

From getting out on the water and touring our historic sites, to feasting on Chesapeake Bay cuisine and embracing our lively arts scene, to exploring our boutiques and speciality shops, you’ll find plenty of things to do in Annapolis before calling it a day at one of the city’s charming historic inns or hotels.

1. Tour the US Naval Academy

The US Naval Academy has been training officers for the U.S. Navy and Marine Corps since 1845. Watch the midshipmen in noon formation; visit the Naval Academy Museum’s world-class exhibits; dine with midshipmen at the Drydock Restaurant; and catch a Navy sporting event.

2. Get Out on the Water

As the gateway to the Chesapeake Bay, Annapolis and the surrounding countryside boast more than 500 miles of shoreline. Learn to sail from the best of the best; unwind aboard a public sail or cruise; charter a boat; or hone your stand-up paddle boarding, canoeing or kayaking skills. Want to get around like the locals do? Ride the water taxi to your favourite restaurant or historic attraction.

3. Feast on Chesapeake Bay Bounty

America’s Sailing Capital is famous for its fresh-from-the-bay seafood. Known by many as striped bass, rockfish is a prized local favourite, as are crabs any way you like them! Annapolis is filled with culinary delights ranging from the simple to the sublime. Whether you roll out the paper and roll up your sleeves for an authentic Maryland crab feast — watching watermen bring in the catch — or you unwind in an elegant indoor setting with a window’s view of the water, Annapolis is the perfect place to indulge in the bounty of the Chesapeake Bay. 

4. Discover Annapolis History

Called a Museum Without Walls, Annapolis has more 18th-century brick buildings than any other city of comparable size in the nation — including the homes of Maryland’s four signers of the Declaration of Independence. The Maryland State House is the oldest in continuous legislative use. The Banneker-Douglass Museum documents Maryland’s African American history from the 1600s to the present day. Housed in an old oyster packing plant, the newly redesigned Annapolis Maritime Museum & Park chronicles life on the Chesapeake Bay then and now.

5. Commune With Nature at Parks & Natural Landmarks

Home to global research on coastal ecosystems, the Smithsonian Environmental Research Center invites visitors to explore its 2,650-acre campus that spans forests, wetlands, marshes and 15 miles of protected shoreline. Learn of archaeological finds and the ongoing reconstruction of the Lost Town of London at Historic London Town and Gardens. Launch a boat or spend the day swimming, fishing or crabbing at the 786-acre Sandy Point State Park. Bike our Baltimore & Annapolis Trail or take a hike at Quiet Waters, one of eight regional parks beckoning outside exploration and fun.

6. Shop ’til You Drop

In search of the perfect gift? For one-of-a-kind boutiques, stroll Annapolis city centre, Eastport and West Annapolis. Reconnect with national retailers and speciality shops at Westfield Annapolis. For the largest outlet and value retail shopping destination in Maryland, head to Arundel Mills. Annapolis Town Centre at Parole offers high-end shopping and a host of dining options.

7. Meet the Locals at Festivals & Events 

No matter the season, festivals and events abound in Annapolis and the surrounding countryside. From the First Sunday Arts Festivals, Dinner Under the Stars, World Largest Crab Feast and Wednesday Night Sailboat Races of Annapolis’s city centre; to the Maritime Republic of Eastport’s quirky Sock Burning, Slaughter Across the Water and .05K run; to West Annapolis’s Oktoberfest and European Christmas Market; to the second largest Renaissance Festival in the nation in the Annapolis countryside — there are always clever and creative ways to hang out with the locals.

8. Celebrate the Countryside

Minutes from the heart of Annapolis, scenic byways lead to maritime villages where fishermen still ply the waters of their ancestors and heritage sites shed a light on the lives of watermen through the centuries. The rhythm of life in the Annapolis countryside moves to the tides and the seasons. It’s quaint and quiet, but there’s luxury, too: A modern waterfront resort and marina is the perfect spot for an overnight stay. 

9. Experience the BWI-Arundel Mills Region

Anchored by BWI Thurgood Marshall Airport the BWI-Arundel Mills Entertainment District boasts the largest retail shopping outlet in Maryland as well as Live! Casino & Hotel, featuring slots and table games, a selection of acclaimed restaurants and a 4,000-seat live entertainment venue. For family fun, there’s Dave & Buster’s, Mission Escape Rooms, Medieval Times Dinner & Tournament and more!

10. Explore the Nooks & Crannies of Annapolis  

Annapolis has a host of unique activities and experiences to choose from. Here are some insider favorites: Hang out at City Dock, the heart and soul of Annapolis — a place to see and be seen! Enjoy home-made ice cream while watching boats strut their stuff at Ego Alley. Tour the last remaining screw pile lighthouse in its original location on the Chesapeake Bay. Enjoy a free summer evening concert. Spend an afternoon on Maryland Avenue. Learn about life in colonial Annapolis at the home and reconstructed 18th-century pleasure garden of Declaration of Independence signer William Paca. Feast your eyes on the Most Beautiful Doorway in America at the Hammond Harwood House. And that’s just the beginning!

Learn more about what an Annapolis holiday has in store for you, or request a free visitors’ guide to plan your visit! 

Related: 
Outdoors & Nature
Shopping
Wine & Cuisine
City Adventures
History & Culture

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