Located along the shores of the Chesapeake Bay is one of America’s oldest and most beautiful cities. Annapolis, Maryland’s capital, blends maritime culture with a uniquely rich American history. Visitors will be enchanted by Annapolis’ thriving Main Street, quaint 18th-century neighborhoods, historic landmarks, and unique cuisine. A stroll through downtown reveals colonial-era buildings, vibrant art galleries, and cozy restaurants serving local seafood such as Chesapeake blue crab.
I’ve visited Annapolis numerous times since moving to the Washington, D.C. area—whether to go sailing with family and friends, wander historic streets, explore cultural sites, or savor the local food. Each visit is just as fun and memorable as the last.
The History of Annapolis
The history of Annapolis dates back to the 17th century. Originally known as Providence, the area was settled by Puritans from Virginia in 1649. It was later renamed Anne Arundel’s Towne in honor of Lord Baltimore’s wife. In 1694, it became the capital of the Maryland colony and was renamed Annapolis in honor of Princess Anne of Denmark and Norway, who later became Queen of England. The town flourished as a center of commerce, governance, and maritime trade thanks to its strategic location on the Chesapeake Bay.
After American independence, Annapolis briefly served as the nation’s capital from 1783 to 1784. It was in the Maryland State House where George Washington famously resigned his commission as commander-in-chief. Annapolis also hosted the 1786 Annapolis Convention, which laid the groundwork for the Constitutional Convention. Over time, it evolved into a hub of education and culture, home to the U.S. Naval Academy (founded in 1845) and numerous preserved colonial buildings, making it one of the best-preserved historic cities in the U.S.
Annapolis offers a perfect blend of scenic charm and cultural discovery. Here are some of my favorite places to visit when exploring this waterfront gem.
Historic Downtown Annapolis
A great place to begin a tour of Annapolis is the historic downtown, centered along Main Street. Visitors step back in time as they walk the narrow brick streets lined with Georgian-style buildings. The area is home to boutiques, galleries, private homes, and colonial landmarks. The western edge of downtown includes State Circle and Church Circle, which surround the Maryland State House and St. Anne’s Parish. Nearby, the Annapolis Visitors Center provides maps, brochures, and helpful staff to assist in planning.
Maryland State House – Just north of Main Street on State Circle sits the stately Maryland State House, the oldest state capitol in continuous legislative use. It holds a unique place in American history, having briefly served as the U.S. Capitol from 1783 to 1784. Visitors can stand in the very room where George Washington resigned his commission as commander-in-chief, a powerful moment in history, and a symbolic act that helped solidify civilian control of the military. Across from the State House is the Government House, a Georgian-style mansion serving as the governor’s residence since 1870, with seven public rooms displaying historic art and collections. A good dining option on State Circle is Harry Browne’s which serves Chesapeake and American fusion fare.
St. Anne’s Church and Church Circle – At the center of Church Circle stands St. Anne’s Episcopal Church, one of Annapolis’ oldest congregations, dating to 1692. The current structure was built in the mid-1800s. Its historic graveyard and shaded grounds offer a peaceful escape from the bustle of downtown.
Banneker-Douglass-Tubman Museum – Maryland’s official African American heritage museum, the Banneker-Douglass-Tubman Museum, is housed in the historic Mount Moriah AME Church. The church was built by the free African American community on land owned by a formerly enslaved woman. Named after three Marylanders who changed the course of history – Benjamin Banneker, Frederick Douglass, and Harriet Tubman, it features powerful exhibits on civil rights, education, and social justice.
Main Street – Main Street is the vibrant heart of Annapolis, extending from Church Circle to the waterfront. The thriving street is lined with brick sidewalks, gas lanterns and 18th- and 19th-century colonial buildings. The street slopes downward offering scenic views of the bay. Visitors can browse an eclectic mix of boutiques, art galleries, coffee shops, and restaurants serving a variety of cuisines. Several restaurants, like Chick and Ruth’s, serve Maryland favorites like crab cakes and oysters. Street performers and festivals enliven the corridor throughout the year. Nearby is the William Paca House and Garden, an impeccably restored Georgian mansion once home to a signer of the Declaration of Independence.
The Annapolis Waterfront and Ego Alley – Visitors can reach the Annapolis waterfront and Ego Alley at the end of Main Street. Ego Alley, a narrow waterway leading to Annapolis Harbor, got its nickname due to the numerous luxury yachts and sailboats that come here to dock, or just be seen. The alley and waterfront area are lined with a lively public promenade, the Annapolis Market House, shops and seafood restaurants and pubs offering scenic harbor views. One of my favorites is Choptank, which serves steaks, seafood, and Maryland style crush cocktails, while offering a prime spot to view the activity along Ego Alley. A nearby famous restaurant is Middleton Tavern which sits across from Ego Alley. Some of its patrons have included George Washington, Thomas Jefferson and Benjamin Franklin.
In warmer months, harbor cruises and water taxis provide unique perspectives of the city from Chesapeake Bay. Departing from City Dock or Ego Alley, the boats glide along Spa Creek and into the broader Chesapeake Bay, offering views of historic sailing ships, elegant waterfront homes, and the iconic U.S. Naval Academy. Local guides narrate Annapolis’s maritime history—from colonial-era trading routes to modern naval traditions. During the spring and fall, the Annapolis Boat Shows are held along the waterfront and are premier maritime events on the East Coast. I’ve attended the fall show several times and highly recommend it. The show draws sailboat and powerboat builders, gear manufacturers, and marine enthusiasts, with hundreds of boats on display. Attendees can tour luxury yachts and other watercraft, take a schooner tour in the harbor, and attend seminars and social gatherings, all while enjoying the festive waterfront atmosphere.
The U.S. Naval Academy
One of my favorite sites in Annapolis is the beautiful and stately campus of the U.S. Naval Academy. It sits on nearly 340 acres immediately north of the historic downtown on a peninsula surrounded by the Severn River. The campus is the crown jewel of Annapolis, with the dome of the Naval Academy Chapel defining the city’s skyline. The academy was established in 1845 as a Naval School with just 50 midshipmen. Today, the Academy prepares over 4,000 young men and women to enter the lowest commission ranks of the US Navy and Marine Corps. The campus is a peaceful escape from the nearby downtown, and contains historic buildings, statues, monuments, gardens and athletic fields. Visitors can take a guided tour through the picturesque campus, known as “the Yard,” to see highlights like the grand Naval Chapel, the crypt of John Paul Jones, and Bancroft Hall—the largest dormitory in the U.S. The Naval Academy Museum, located in Preble Hall, offers two floors of exhibits of maritime artifacts and naval history. Visitors walking through the campus will see the daily rituals of midshipmen, providing a glimpse into life at one of the country’s premier military institutions.
For those visiting around Memorial Day during Graduation Week, also known as Commissioning Week, there are numerous activities to partake in. The Herndon Monument climb is one such fun spectacle, in which plebes, having completed their first year, work together as a team to ascend a 21-foot-tall lard-greased monument to replace a plebe’s hat with an officer’s hat on top. The Naval air show takes place during Commissioning Week, and a highlight is the Blue Angels which put on a spectacular display in the skies above Annapolis. Visitors must show a valid ID to access the campus.
The Eastport Neighborhood
South of downtown and Spa Creek is Eastport, a neighborhood built on a peninsula surrounded by Spa Creek, Annapolis Harbor, and Back Creek. It was once a separate fishing village before merging with Annapolis in 1951. Eastport is accessible from downtown by the Spa Creek Bridge which leads to charming residential streets, waterfront restaurants and pubs, sailing schools and numerous marinas. Eastport has a laid-back, maritime vibe with a small coastal village feel. After a day of sailing, I’ve enjoyed dining at numerous restaurants in Eastport. The Boatyard Bar and Grill offers delicious seafood, including Maryland crab cakes, in a building designed with a nautical theme. Along Back Creek is Davis’ Pub, a laid back neighborhood joint offering seafood, burgers, salads, and a tasty chicken and sausage gumbo. Vin 909 offers Mediterranean and California inspired cuisine, and some of the best thin crust pizza I’ve had, served in a variety of styles.
There is a tongue-in-cheek rivalry between downtown Annapolis and Eastport as displayed in the annual “Slaughter Across the Water” tug-of-war held in early November. It started in 1997 when the ‘Maritime Republic of Eastport’ jokingly declared independence from Annapolis, when the Spa Creek Bridge was temporarily closed for repairs, cutting off Eastport from the rest of the city. Since then, every year each team of 33 tuggers compete along the bridge for championship bragging rights.
Annapolis Maritime Museum – The Annapolis Maritime Museum is located in the former McNasby Oyster Company building on Back Creek. The museum presents the maritime heritage of Annapolis and the ecology of the Chesapeake Bay. Interactive exhibits display traditional boatbuilding techniques, watermen culture, and the region’s unique seafood industry. Exhibits are interactive and family-friendly, and its location offers beautiful bayfront views.
Historic London Town and Gardens
Historic London Town and Gardens is a 23-acre living museum located in Edgewater, eight miles south of Annapolis. Nestled on the South River, London Town was founded in 1683 and was once a bustling seaport and ferry crossing. The town thrived as an important colonial tobacco-export hub before declining in the late 18th century when trade routes shifted. Today, the museum displays Maryland’s colonial past. The centerpiece is the William Brown House, built in 1760. It was originally an upscale tavern and later an almshouse, now preserved as a National Historic Landmark. The museum has numerous gardens including a woodland garden, ornamental garden, and a children’s sound and sensory garden.
Getting To and Around Annapolis
Getting to Annapolis is convenient whether you’re arriving by car, bus, or boat. Annapolis is located about 30 miles east of Washington, D.C., and 25 miles south of Baltimore, and accessible via U.S. Route 50 and Interstate 97. Travelers flying in can use Baltimore/Washington International Thurgood Marshall Airport (BWI), which is a 30-minute drive away. From there, rental cars, shuttles, and ride-sharing services provide easy access to the city. Intercity bus services, including Greyhound and Megabus, also offer routes to nearby hubs with connections to Annapolis. For boaters, Annapolis’s location on the Chesapeake Bay and its many marinas make it a favorite destination for arriving by water.
Annapolis is accessible by Amtrak (via nearby Baltimore or New Carrollton), where visitors can connect to intercity Maryland Transit Authority (MTA) buses.
Once in town, navigating Annapolis is relatively easy. The compact downtown is pedestrian-friendly, and free circulator shuttles help visitors explore with ease. Annapolis Transit operates color-coded bus routes—plus two free Downtown Shuttles (operating every ten minutes) — that conveniently connect downtown, neighborhoods like Eastport, and local attractions such as the Naval Academy. At the waterfront, the Watermark Water Taxi offers harbor service, running between City Dock, Spa Creek, Back Creek, and Eastport, offering a scenic and stress-free way to get around.
For bicycling, e-bikes and scooters are readily available throughout the city, offering an eco-friendly way to explore downtown. Ride-hailing services and traditional taxis are also available.
