Annapolis once served as the capital of the United States during the Revolutionary War. Today, it’s a town full of historic buildings that will take you back to that eventful period.
Annapolis also has one of the country’s best waterfronts. It’s the perfect place to sail, look out onto the water, and eat delicious seafood. Whether you’re enjoying it by boat, bike, or trolley, you’ll have plenty to see.
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William Paca House
This historic house is dedicated to William Paca, one of Maryland’s 4 signers of the Declaration of Independence and the state’s governor in the 1780s. His estate was built between 1763-1765 and has been restored to its original glory. It includes a mansion, summer house, and 2 acres of formal gardens. Visit for a sense of what life was like during the American Revolution in Annapolis.
Maryland State House
This equally historic building is the oldest still-used statehouse in the United States. It also served as the capital from 1783-1784. Important moments in history occurred here, including George Washington’s resignation as commander in chief of the Continental Army as well as the ratification of the treaty of Paris. It may only take a few hours to visit, but it’s worth the time.
Annapolis Historic District
This area is a designated National Historic Landmark District and the best place to get a sense of the history of the city. Make sure to take the Heart of Annapolis Tour where you’ll ride with an expert on an electric cruiser. They’ll give you a chance to see the major sites as well as lesser-known side streets and locations that you may otherwise miss.
Great Frogs Winery
This old tobacco farm was turned into a winery in 1999. The sandy soil was the perfect place for growing grapes. They’re used to make over a dozen white, rose, and red French Bordeaux varities and blends. You can spend a weekend tasting wines, cheese, and charcuterie. You can also picnic at the tobacco barn or walk amongst the vines.
Banneker-Douglass Museum
This can’t-miss spot is named after 2 major historical figures; scientist and writer Benjamin Banneker and abolitionist Frederick Douglas. It sits inside the historic Mount Moriah African Methodist Episcopal Church and serves as Maryland’s official museum of African-American history. It’s small but has a range of educational exhibits on art, music, and history. It also celebrates Maryland’s other notable African-American figures such as Harriet Tubman and Thurgood Marshall.
Waterfront Hotel
This ornate hotel is part of Marriot’s Autograph Collection. The upstairs rooms provide views of downtown Annapolis and Spa Creek. The Pussers Caribbean Grille downstairs adds to the experience by giving you a chance to taste the food of the British Virgin Islands.
Eastport
This community is directly across from the Spa Creek Bridge. It was founded in 1998 and has developed its own identity since then; it has its own flag and yacht club. It also hosts the Slaughter Across the Water every year, and you can watch the Wednesday Night boat races at the Eastport’s Boatyard Bar and Grill. You’ll also get great views of downtown and the Naval Academy.
City Dock
This place is also known as Ego Alley. It’s where the everyday visitor goes to watch pedestrians or see rich captains try to sail their expensive boats through the narrow area. You can also enjoy an ice cream cone from Storm Bros. Ice Cream Factory while you’re watching.
Chick and Ruth’s Delly
If you’re hungry for breakfast, visiting this location is one of the best things to do in Annapolis. It opened in 1965 and has been a local favorite ever since. The food is delicious, especially the crab and cheese omelet. The staff all assemble for the Pledge of Allegiance at 8:30 am on weekdays and 9:30 am on weekends. It’s a long-standing tradition worth experiencing.
Annapolis Ice Cream Company
There are a few better things to do in Annapolis if you’re screaming for ice cream than stopping by this shop. All 36 of its rotating flavors are made fresh almost every day. They’re so fresh and premium that they supposedly take hours to melt.
Boat Rides on the Chesapeake Bay
The Chesapeake Bay is one of the most famous waterways in the United States, and the best way to experience it is to get right out onto it on a boat. 40 minutes on the Harbor Queen will take you around the harbor, past the Naval Academy, and near the Chesapeake Bay Bridge. 2 hours on the Schooner Woodwind will take you on a search for local lighthouses, and you may even get to be part of the crew. You can even rent an electric boat that holds up to 11 passengers.
Kunta Kinte-Alex Haley Memorial
This unique memorial celebrates Kunta Kinte, the inspiration of the novel and TV series Roots. It includes a sculpture of Haley reading to children, 10 bronze plaques, and a 14-foot compass rose. It’s free to visit and open 24/7.
United States Sailboat Show
If Ego Alley didn’t scratch your urge to stare at sailboats, go to the United States Sailboat Show on the Annapolis Dock. You’ll see some of the best and brightest boats on the market, and it’s an interesting sight whether you’re window shopping or going home with a new vessel.
Wednesday Night Sailboat Races
Annapolis, the Sailing Capital of the World, hosts over 100 yachts from April to August. Its Wednesday night races are a popular attraction for locals and tourists. The best way to experience them is to sit on the deck off either the Woodwind or the Woodwind II. Cheer them on to first place.
US Naval Academy
The Academy was founded in 1845. During a 90-minute tour, you’ll see the Atheltic Hall of Fame, Bancroft Hall, Tecumseh statue, Naval Academy Chapel, and crypt of John Paul Jones. You may also get a chance to see the noon meal formation or hear a public performance by the Naval Academy Band or the Academy’s many choral and instrumental ensembles.
Annapolis Maritime Museum
The last oyster packing plant in Annapolis was transformed into this museum. It celebrates the city’s history of boat building and its long-standing oyster industry. It also features an over 850-gallon aquarium and one of the city’s only public beaches. You’ll see a range of exhibits, such as the 1868 Oyster Wars Canon and oyster boats such as the Miss Lonesome.
Fort Meade NSA Cryptologic Museum
This museum is only 20 minutes away from the city’s center and is the only one of its kind. It opened in 1993 and focuses on cryptology, the art of creating and cracking codes. Taking a tour lets you see all it has to offer, but inquisitive visitors can stop by the research library.
Ram Heads Tavern
This spot has hosted local musicians and comedians for over 20 years through its Rams Head on Stage program. Visit to see the next great star before they make it big. You’ll also enjoy a top-notch dining experience; the staff will deliver your food and drinks while you enjoy the show.
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Cantler’s Riverside Inn
This site offers some of the best seafood in the entire state of Maryland, and that’s saying something. The tubs in the back are full of crabs and fish fresh off the boat, and you can also walk the Crab and Oyster Trail.
Quiet Waters Park
This park spans 340 acres with a 7-mile paved path for bikers and joggers and formal gardens to trek through. It’s the perfect park for art-lovers with various sculptures and 2 art galleries. It also has a playground for children, a dog park for your furry friends, and canoes and kayaks to rent if you want to get out on the water. You may be able to catch outdoor concerts in the summer or skate on the ice rink in the winter.
Sandy Point State Park
This park sits on the banks of the Chesapeake Bay. It has a beach with a playground and lifeguard stations, picnic areas, a pavilion, a bathhouse, and plenty of food. You can rent a boat on the marina or explore the Eastern Flyway to see migratory birds. There’s also a nature center and interpretive center to learn about the local wildlife and plants.
Hammond-Harwood House
This spot is also known as the jewel of Annapolis. It’s named after William Buckland, an indentured servant who later became an architect and began working on the house in the 18th century. He created it in the Anglo-Palladian style. You can take a 50-minute guided tour or get an appointment for a 2-hour in-depth tour for $20.
St. Anne’s Church
This historic church, completed in 1704, was once the only chapel in Annapolis. It was torn down and expanded in 1775, but the Revolutionary War kept it from being finished until 1792. It was destroyed by a fire in 1858, and the final version, built in 1859, is still standing today. It’s an active Episcopal parish with stained glass windows and gorgeous architecture.
Trolley Tours
Taking a trolley tour is one of the best things to do in Annapolis because it lets you see so much of the city in a single hour. You’ll see Victorian houses and colonial mansions, the Severn River, and other attractions such as the Naval Academy.
Annapolis, Maryland, is a historic city that played a major part in the founding of the United States of America. It’s also a beautiful area with plenty of waterside views and natural beauty to enjoy.
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