‘It's all still here.' This seafaring town brings the past to life

CNN

3 days ago

See More Videos It's Sunday night at Middleton Tavern, where a handful of drinkers at the rustic wooden bar are surrounded by glimpses of America's colonial past.
Copper pots hang over a fireplace, while seascape paintings, farm tools, old naval uniforms and models of sailing ships adorn the walls. The patio offers views of Annapolis' City Dock, where Chesapeake Bay watermen once brought in the day's catch.
And the tavern itself dates to 1750 – before America became a country – when Horatio Middleton opened it to lodge travelers crossing the bay on his ferry. If you believe the local lore, George Washington and Benjamin Franklin once drank here.
'This is one of the oldest – if not the oldest – bars in Maryland,' says bartender Steve Frederick, an amiable guy with a lanky frame and a trucker hat. 'There's a lot of history here.'
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Share your picks for our top towns in 2026 Indeed, there's a lot of history throughout this cozy waterfront city, whose narrow streets, brick sidewalks and handsome Georgian buildings could serve as an 18th-century movie set.
But Annapolis, Maryland's capital and a 45-minute drive from Washington, D.C., offers visitors much more than historic charm. A key port on the Chesapeake, it provides numerous ways to explore the Bay, from sunset cruises to outings aboard a historic skipjack, a working sailboat once used for dredging oysters.
The city of 40,000 also is home to the US Naval Academy, whose uniformed midshipmen are seen all over town. And seafood lovers can feast at white-tablecloth restaurants or roll-up-your-sleeves waterside joints serving steaming piles of Maryland's famous blue crabs.
Many of these attractions lie within Annapolis' well-preserved, walkable downtown, lined with stately brick homes and charming row houses.
'Annapolis is amazing, in that when you walk the historic district … it's all still here. It's all real – it's not something that's been recreated,' says Mary-Angela Hardwick, a vice president at preservation group Historic Annapolis.
'I mean, if the buildings could talk they would be able to tell you who had walked these streets – Thomas Jefferson, James Madison, George Washington … they all were here,' she adds. 'It's really like traveling back in time. We call it a museum without walls.'
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Founded by English settlers in the 1600s and named for England's Princess Anne, Annapolis was a bustling colonial capital. Its location on the Chesapeake at the mouth of the Severn River was ideal for shipping tobacco, then a leading Maryland cash crop. The city also was a seat of government and even served as America's first peacetime capital for nine months in 1783-1784.
By state capitol standards, the Maryland State House is a small, understated building — there's no grand, neoclassical dome. But as the nation's oldest state house still in legislative use, it's full of history and worth a visit. It was here on December 23, 1783, that George Washington formally resigned as commander of the Continental Army — a major event in the history of the fledgling country. And Congress met at the state house in 1784 to ratify the Treaty of Paris, officially ending the Revolutionary War.
The moment is immortalized with a life-size bronze statue of Washington, placed in the approximate spot in the old Senate Chamber where he addressed Congress. An original copy of his resignation speech is on display as well.
Many other handsome historic buildings are within a short walk. Annapolis is the only American city where you can see the surviving homes of each of its state's signers of the Declaration of Independence. The most prominent of the four homes (not all are open to the public) is the William Paca House, a Georgian brick mansion built in the 1760s by the man who later became Maryland's third governor. Historic Annapolis offers public tours of the Paca house and its elaborate terraced garden, home to rose beds, fruit trees and a small pond.
Like many historic towns on the Eastern Seaboard, Annapolis also harbored ships carrying enslaved people from Africa. The city's status as an 18th-century slave port is chronicled in Alex Haley's famous 1976 novel 'Roots,' whose main character Kunta Kinte landed in Annapolis before being bought by a plantation owner in Virginia.
Today 'Roots,' and the city's legacy of slavery, is commemorated with a memorial on the City Dock featuring a bronze sculptural installation of Haley reading to three children.
The memorial also reflects Annapolis' complicated African-American history as a city that held slave auctions in the early 1800s while also becoming home to a thriving community of free Black people, some of whom owned businesses and were granted the right to vote. Despite being a state where people were enslaved, Maryland sided with the Union during the Civil War.
'Being able to hold both things as true … can be confusing to folks,' says Briayna Cuffie, a volunteer at the Museum of Historic Annapolis. 'Because people associate freedom with the North and enslavement with the South … and we are the border state right in the middle, experiencing all of it.'
Annapolis' status as a commercial hub was eventually eclipsed by Baltimore, whose deeper harbor could host larger, ocean-going ships. But the city remains deeply linked to the waters of the Chesapeake Bay, the nation's largest estuary, and its maritime heritage is still evident almost everywhere you look.
Cross a short bridge from downtown and you'll find yourself in the charming Eastport neighborhood, the traditional heart of Annapolis' commercial fishing and boating industry. Here you'll find boatyards, marinas, shipbuilders, sailmakers and seafood processing plants, along with a growing number of restaurants and a brewery.
The Annapolis Maritime Museum, located in a former oyster canning factory on the banks of Eastport's Back Creek, offers displays on the history and ecology of the Bay, along with rotating exhibits of works by local artists and photographers.
Crabs may be king in Maryland today — especially in the warmer months, when crabbers fan out to harvest them — but for many years the Bay's watermen favored another marine species: oysters.
Annapolis' fisheries hauled in millions of bushels of oysters annually until the early 1900s, when overharvesting decimated the population.
ESSENTIAL ANNAPOLIS
EAT: Fresh Chesapeake Bay seafood at Boatyard Bar & Grill
DRINK: On The Choptank's vast rooftop deck with harbor views
STAY: At the historic Maryland Inn, a short walk from most sights
SEE: The United States Naval Academy, which offers daily tours Because oysters are vital to a healthy Bay ecosystem — a single oyster can filter up to 50 gallons of seawater a day — the museum is highlighting efforts to rebuild oyster reefs and repopulate the mollusks. The results show up on restaurant menus throughout Annapolis.
Today, recreational boating has joined the seafood industry as a key driver of Annapolis' economy. The City Dock features a narrow waterway nicknamed 'Ego Alley' for the showy yachts that tie up there. Sloops and motorboats fill the city's marinas, while its docks and surrounding waters host boat shows, crab feasts, sailing lessons and regattas.
'There's a lot to do,' says Eileen Hayden, a maritime museum volunteer, noting the city's festive spirit and packed calendar of nautical events. 'Annapolis always wants to have a party about something.'
Annapolis is nicknamed 'America's Sailing Capital,' and to fully appreciate the city, it's best to get out on the water for views of its harbor, aquatic life and picturesque skyline, along with such nearby landmarks as the four-mile-long Chesapeake Bay Bridge and the 150-year-old Thomas Point Shoal Lighthouse.
Visitors will find no shortage of boating options, from water taxis and fishing charters to two-hour sailing cruises aboard the Woodwind schooners, whose crew may even let you steer and help raise the sails. Or you can book a heritage tour on the Wilma Lee, the maritime museum's 47-foot skipjack, which was built in 1940 as part of the last commercial sailing fleet for fishing in the country.
A trip to Annapolis isn't complete without a visit to the Naval Academy, established in 1845 on the site of an old fort. The rigorous institution has produced 55 NASA astronauts — more than any other school — plus such notable alumni as President Jimmy Carter, business tycoon Ross Perot, football great Roger Staubach and NBA Hall of Famer David Robinson.
A brief walk from the City Dock, the academy's handsome waterfront campus — known locally as the Yard — offers daily, 90-minute walking tours of its history, unique culture and many sites of interest.
Among the highlights:
Bancroft Hall, a grand Beaux Arts building which houses all 4,400 midshipmen ('midshipmen' is a rank; about a third of the academy's students are women) and is the largest dormitory in the country. The sprawling complex has almost 5 miles of corridors and its own zip code, and its massive dining hall serves more than 13,000 meals daily. For an added bonus, time your visit to witness the noon meal formation ceremony, at which the midshipmen line up in battalions — along with the USNA band — and march into Bancroft Hall for lunch.
Lejeune Hall, a sports facility housing the academy's two Heisman Trophies and an Olympic-size pool where all midshipmen must pass rigorous swimming tests before graduating. 'You may not know how to swim when you arrive (at the academy),' one recent tour guide said. 'But you won't leave here until you do.'
The Naval Academy Chapel, whose striking dome is a dominant feature of Annapolis' skyline. Its soaring interior features elaborate stained glass windows designed by Louis Comfort Tiffany, some of them depicting naval battles. Underneath the chapel is a crypt with a sarcophagus holding the remains of John Paul Jones, considered the father of the Navy.
The US Naval Academy Museum, which offers exhibits on the history of sea power, foreign flags captured in battles and an impressive collection of antique ship models.
Annapolis and the USNA are especially festive during Commissioning Week, an eight-day celebration each spring with parties, a parade and an aerial performance by the Blue Angels. The week culminates with the academy's graduation ceremony, where midshipmen are officially commissioned as officers and fling their caps into the air in triumph.
Annapolis offers no shortage of worthwhile places to eat, drink and be festive. History buffs will appreciate the colonial charm of Reynolds Tavern, which dates to 1747 and looks the part. Music lovers have long flocked to the Ram's Head, a tavern and adjoining stage featuring national touring acts. Downtown's Main Street has a mix of restaurants serving steak, tacos, teriyaki and Thai food.
For a quintessential Chesapeake Bay experience, though, it's hard to top a meal of local seafood.
The most popular restaurant in town may be the Boatyard Bar & Grill, a lively Eastport hangout whose walls are festooned with college banners, nautical scenes and a mounted blue marlin. Its menu offers all the local hits: crab soup, oyster shooters, fish tacos and, of course, lump crab cakes.
The Boatyard is one of many Annapolis eateries that lay claim to serving the area's best crab cakes. Other worthy contenders in Eastport alone include its upscale neighbors Carrol's Creek Cafe and O'Leary's Seafood or even Davis' Pub down the street, a homespun joint also known for its crab pretzel. Be forewarned, though: a pair of crab cakes at many places in town will set you back $50.
In Annapolis you're never far from the Bay or its tributaries, which means – yay! – waterside dining. Downtown's best views are at The Choptank, a newer, splashy seafood place whose large rooftop deck offers sweeping vistas of the harbor and City Dock, making it a prime happy hour spot.
For a classic meal with a laid-back vibe, a 10-minute drive brings you to Cantler's Riverside Inn, a rustic crab house on the peaceful waters of Mill Creek. In the summer months customers come by boat – docking is free – and gather on the deck to drink beer and chow down on blackened rockfish, peel-n-eat shrimp or blue crabs slathered in Old Bay seasoning.
Finally, don't miss Chick & Ruth's, a beloved greasy spoon that's been slinging diner fare for 60 years in a bustling Main Street space with a lunch counter and cozy booths. Its hearty menu offers everything from crab omelets to sandwiches named for local politicians (a cheesesteak inspired by former Maryland Gov. Larry Hogan is called Hogan's Hero.) If you're feeling brave, tackle the 6-pound milkshake – finish it along with a large sandwich and they'll put your photo on the wall.
This Gold Rush-era boomtown still delivers culinary riches