Named for Anne, Queen of Great Britain (1665-1714), Maryland’s state capital first came to the fore in the 17th century and has kept much of its historic architecture.
On the streets of the Colonial Annapolis Historic District you’ll find yourself in a prosperous Georgian city, converging on grand circles, one of which holds the United State’s oldest functioning state capitol.
“America’s Sailing Capital”, has a persisting nautical culture, with boat shows, a waterfront district embellished with glitzy yachts and a skyline defined by the august architecture of the U.S. Naval Academy, founded in 1845.
In Annapolis you can tour the house of a Founding Father, take the wheel of a schooner and see the place where Kunta Kinte first set foot on American soil as an enslaved man in 1767.
1. Colonial Annapolis Historic District
The first thing you’ll notice when making your way around the historic downtown area is the absence of a grid system.
At the turn of the 18th century, Annapolis was laid out by Governor of Maryland, Francis Nicholson (1655-1727) as a Baroque planned city, with grand circles that have radiating streets.
At the center of one is the Maryland State House, while another holds St. Anne’s Church (1692).
A flourishing economy, driven by shipping and “planting”, gave rise to institutions of higher learning, culture, sport (namely horse racing) and splendid mansions in sumptuous grounds, that would later entertain Founding Fathers.
Annapolis has more original 18th-century Georgian architecture than any other city in the country, and we’ll talk about two residences you can visit later in this list.
2. Annapolis City Dock
Flanked by low, historic storefronts, the brick-paved Main Street leads down from St. Anne’s Church to the place where Annapolis knits with the waters of the Chesapeake Bay.
Main Street and the waterside Dock Street, are ideal for a wander on a summer’s day, and are packed with pubs, inns, restaurants, galleries and intriguing boutiques.
Small, independent businesses and artisanship prevail here, as they have done for 350 years. Many of the eateries by the water have outdoor seating, and you can watch the sleek yachts gliding around the turning basin, Ego Alley.
City Dock sets the scene for many annual events in Annapolis, from boat shows to the Fourth of July Fireworks and the Military Bowl Parade in December.
3. Maryland State House
Taking center stage in the State Circle, the Maryland State House (1772-1797) has the distinction of being the nation’s oldest state capitol in continuous legislative use, and the only one to have served as the nation’s capitol (1783-1784).
The wooden dome, which appears on the Maryland state quarter, is the largest in the United States to be constructed without nails.
This dignified Georgian building is open to the public daily during normal hours. It was in the Old Senate Chamber that Washington resigned his commission as commander-in-chief in 1783 and the Treaty of Paris was ratified, marking the official end of the Revolutionary War.
There’s an exhibit for this momentous event, as well as several monuments for noteworthy figures like Harriet Tubman (1822-1913) and Frederick Douglass (1818-1895).
4. U.S. Naval Academy
Right by the Colonial Annapolis Historic District, the U.S. Naval Academy has been a fixture in the city for close to 180 years.
You won’t need an advanced reservation to take a 90-minute guided tour of the solemn campus here.
Organized via the Armel-Leftwich Visitor Center, these take place several times a day, leading you past all of the academy’s many architectural and historical highlights.
The ideal time to be here is just before midday, in time for the spectacle of thousands of Midshipmen marching into Tecumseh Court, all framed by the fine Beaux-Arts Bancroft Hall, in a tradition that goes back to 1905.
The Naval Academy Chapel is an unforgettable part of the experience, dating to 1908 and containing the remains of John Paul Jones (1747-1792), The Father of the American Navy, in its crypt.
5. U.S. Naval Academy Museum
Preble Hall at the U.S. Naval Academy is one of the main ports of call for visitors, housing the U.S. Naval Academy Museum.
This has two stories of exhibits, mixing interactivity, video and audio with masses of interesting artifacts.
You’ll explore the history of seapower, the evolution of the U.S. Navy and the U.S. Naval Academy’s history of producing officers capable of leadership.
In the museum’s holdings are medals, weapons, uniforms, flags, navigation instruments, model ships, books, photographs and some 1,200 paintings.
One of the most celebrated exhibits includes picks from a collection of 20+ ship models crafted from bone by French prisoners of war during the Napoleonic Wars.
6. William Paca House
Several of the magnificent residences in the Colonial Annapolis Historic District are open to the public, and demand a visit.
One with serious historical weight is the home of lawyer William Paca (1740-1799), a signatory in the Declaration of Independence.
He was responsible for much of the house’s design, and most of the property, inside and out, has been restored to its original appearance from the mid-1760s.
Guided tours depart hourly on the half-hour and take you through expertly preserved rooms including the parlor, grand foyer, kitchen and several bedrooms, informing you about the occupants, from family members to servants to enslaved laborers.
Admission includes a self-guided visit to the gorgeous, two-acre walled garden, which contains an idyllic summer house.
7. Banneker-Douglass Museum
An important stop in the Colonial Annapolis Historic District is this museum chronicling Maryland’s African American heritage.
The setting is the historic, Gothic Revival Mt. Moriah African Methodist Episcopal Church, built in 1876 and gaining its current appearance in 1896. For almost a century, this building served as the meeting hall for the First African Methodist Episcopal Church.
The museum’s permanent exhibition is Deep Roots, Rising Waters: A Celebration of African Americans in Maryland, from 1633 through the present day.
You’ll find out about Maryland’s first African American settler, discover almanac author Benjamin Banneker’s correspondence with Thomas Jefferson, hear an anti-slavery speech by reformer Frederick Douglass and see how Thurgood Marshall strove to change the country’s education system.
There are always worthwhile temporary exhibits, as well as events including panel discussions, workshops, unveilings and anniversary celebrations.
8. Kunta Kinte – Alex Haley Memorial
At the City Dock you’ll be confronted by the reality that this place was a crucial hub for the Atlantic slave trade in the 18th century.
Pulitzer Prize-winning Roots author Alex Haley (1921-1992) said that the most emotional moment of his life occurred in 1967 when he stood at the spot where his ancestor, Kunta Kinte, first set foot in the New World as an enslaved man 200 years before.
A stirring memorial has been erected here, depicting Haley reading to a group of children of different ethnic backgrounds.
Part of the same memorial is the Story Wall, with ten plaques along the dock, each with an excerpt from Roots, recording Haley’s family story.
Finally, in front of Market House across the street is the Compass Rose, a map of the world inlaid in multicolored granite with a bronze centerpiece.
Fourteen feet in diameter, with Annapolis at the center, this feature recalls the compasses used by seafarers for hundreds of years.
9. Chesapeake Blue Crab
The Chesapeake Bay is synonymous with the blue crab, Maryland’s state crustacean and by far its largest fishery.
According to the most recent estimate there are 282 million blue crabs living in the bay, about 160 million of which have reached maturity.
More than a third of the nation’s annual catch comes right from this place, in an industry worth tens of millions of dollars to the region.
Cracking steamed or boiled crabs is part of the experience at seafood restaurants in Annapolis, and many spots even offer a crab opening tutorial to help you get started. There’s also Maryland crab dip, crab cakes, soft shell crab and Maryland crab soup to try.
A few locations to get you started are Cantler’s Riverside Inn (458 Forest Beach Rd), Boatyard Bar & Grill (400 Fourth St), Carrol’s Creek Cafe (410 Severn Ave) and O’Learys Seafood Restaurant (310 Third St).
10. Quiet Waters Park
On the wide, final reaches of the South River, about ten minutes south of downtown Annapolis, there’s a 340-acre park with sensational waterfront vistas.
Quiet Waters Park is set where Harness Creek enters the river, and there’s a dock here on the west side where you can rent canoes, kayaks, paddleboards, row boats, pedal boats and bicycles.
Out of the water there are six miles of trails in the park, taking in a beautiful promenade and scenic overlook.
Visit in winter and there’s an ice rink here, with skate rentals for a small fee, while summer brings a much-loved concert series, with performances on Saturdays.
The southern end of Quiet Waters Park is taken up by a dog park, and puppers even have their own beach to frolic on.
11. Navy Midshipmen Football
In the fall Annapolis is swept up in the excitement of the college football season, when the city’s population swells by thousands for every Naval Academy home game.
The Midshipmen play at the 34,000-capacity Navy–Marine Corps Memorial Stadium on the United States Naval Academy campus.
The golden days undoubtedly came in Heisman-winning Roger Staubach’s era in the early 1960s, but Ken Niumatalolo’s time as coach since 2008 has been regarded as a success.
Stadium seating is usually available, but you can also settle down on the grassy bank at the north endzone, and it’s worth arriving early for the traditional flyovers.
12. Sandy Point State Park
At the western end of the iconic Chesapeake Bay Bridge is a 786-acre park on the water, renowned for its popular beach.
Just ten minutes from the historic heart of Annapolis, Sandy Point State Park is somewhere to savor the stunning scenery of the Chesapeake Bay, framed by that bridge, which broke records when it opened in the 1950s.
One curious sight in the foreground is the Sandy Point Shoal Lighthouse, standing in the water about 1,000 feet out, with an Empire-style design and its beacon resting atop a mansard roof.
The sandy swimming beach here is a mile long, and you can rent beach chairs and umbrellas. There’s also a marina with 22 launching ramps, usually renting kayaks, paddleboards and motorboats.
13. Schooner Woodwind
Coming to America’s Sailing Capital you’d be remiss not to head out into the bay with the wind in your hair.
The easy way to do this is aboard one of two 74-foot schooners, Woodwind and Woodwind II. During this experience you can steer the boat and help raise the sails, or simply sit back and take in the scenery.
Departing from the historic waterfront, the cruise takes you past the Naval Academy and into the bay as far as the bridge.
On this voyage you’ll be informed about the local ecology, the intricacies of sailing and the history of Annapolis from a trained guide.
14. Hammond-Harwood House
One of the finest surviving Colonial mansions in the United States is open as a historic house museum in Annapolis.
A National Historic Landmark by architect William Buckland (1734-1774), the Hammond-Harwood House (1774) is unique for having a design inspired directly by a plate in Andrea Palladio’s The Four Books of Architecture (1570).
There’s much to admire in the building’s elegant proportions, formal rooms, carved main portal, garden and a rich collection of painting, furniture and decorative arts.
There’s also history to uncover as you go, including the story of the enslaved people who lived in the house, and the lives of the Hammond and Chase families. All year round, the museum hosts regular special tours, talks, concerts and family programs.
15. United States Sailboat Show
Every October one of the largest and most prestigious in-water boat shows in the world takes place on the miles of docks in downtown Annapolis.
More than 50,000 boaters from around the world take part in this multi-day event, boarding and inspecting hundreds of vessels from every important sailboat manufacturer.
This is a rare opportunity for prospective buyers to make side-by-side comparisons of the latest sailboats. By the water there’s a whole network of tents, with vendors for the latest accessories, gear, clothing and electronics.
You can come for drinks tastings, to chat with industry people, take part in educational programs and connect with other boating enthusiasts.