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Annapolis Walking Tour

Annapolis, United States

Why Walk Annapolis

Annapolis has been Maryland's capital since 1694 and served as the capital of the United States from November 1783 to August 1784, during which time the Continental Congress ratified the Treaty of Paris ending the Revolutionary War. The Maryland State House, topped by the largest wooden dome in America built without nails — constructed using an ingenious system of wooden pegs and iron straps — is the oldest state capitol building in continuous legislative use. The city's compact colonial downtown contains more than 1,500 historic buildings, with over 50 pre-Revolutionary structures, making it one of the densest concentrations of 18th-century architecture in the nation. The US Naval Academy, established in 1845 on a 340-acre campus at the confluence of the Severn River and Chesapeake Bay, trains roughly 4,400 midshipmen. Annapolis calls itself the 'Sailing Capital of the United States,' hosting over 50 regattas annually and serving as home port to hundreds of sailing vessels. The Chesapeake Bay's famous blue crabs are a culinary institution here, with crab houses lining the waterfront.

Free Annapolis Walking Tour with Roamee Pro

Roamee Pro offers a free Annapolis walking tour with audio narration. Explore Maryland State House, US Naval Academy, City Dock, plus hidden gems like Ego Alley and Historic Annapolis walking tour, without booking a group tour.

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Must-See Stops in Annapolis

  • Maryland State House — Completed in 1779, this is the oldest state capitol building in continuous legislative use in the United States, and the only one to have served as the national capitol. The wooden dome, rising 130 feet, was constructed without nails using a system of wooden pegs designed by architect Joseph Clark. Inside the Old Senate Chamber, George Washington resigned his commission as Commander-in-Chief of the Continental Army on December 23, 1783, and the Treaty of Paris was ratified here on January 14, 1784, officially ending the American Revolution.
  • US Naval Academy — Founded in 1845 by Secretary of the Navy George Bancroft, the academy sits on 340 acres along the Severn River and graduates approximately 1,000 officers annually. The Naval Academy Chapel, completed in 1908 in Beaux-Arts style with a 200-foot copper-covered dome, houses the crypt of John Paul Jones, the father of the American Navy, whose remains were transported from Paris in 1905. Bancroft Hall, the single largest dormitory in the world at 33 acres of floor space, houses all 4,400 midshipmen under one roof.
  • City Dock — Known as 'Ego Alley' at its innermost basin where sailboats parade for spectators, City Dock has been the commercial heart of Annapolis since the colonial era when it served as a tobacco shipping port. The surrounding waterfront features the 1760 Middleton Tavern, one of the oldest continuously operating restaurants in America, and the Market House, which has provided fresh provisions since 1858. From spring through fall, the dock bustles with charter boats, water taxis to the Eastern Shore, and the Wednesday evening sailboat races visible from the seawall.
  • William Paca House — Built between 1763 and 1765 by William Paca, one of four Maryland signers of the Declaration of Independence, this five-part Georgian mansion is considered one of the finest colonial homes in America. The two-acre pleasure garden behind the house was buried for decades under a hotel parking lot before being painstakingly excavated and restored in the 1970s using archaeological evidence and a portrait of Paca painted by Charles Willson Peale that showed the garden in the background.

Hidden Gems in Annapolis

  • Ego Alley — The narrow inner basin of City Dock where the water channel dead-ends, creating a natural stage for boaters to cruise slowly past the crowded seawall spectators showing off pristine yachts, vintage wooden boats, and occasionally massive ocean-going vessels that seem impossibly large for the tight channel. The name originated in the 1960s among local sailors, and the Sunday afternoon parade of boats has become an Annapolis institution.
  • Historic Annapolis walking tour — The colonial downtown packs more 18th-century brick buildings per square mile than virtually any American city, with the original street plan laid out by Royal Governor Francis Nicholson in 1695 still intact. The walk passes the 1774 Hammond-Harwood House (one of the finest Georgian residences in America), the Chase-Lloyd House where Francis Scott Key was married, and numerous taverns and merchants' houses with original period details including Flemish bond brickwork and gambrel roofs.

Walking Tip

The historic district is small and entirely walkable. Park at the Navy-Marine Corps Stadium and take the free shuttle downtown.

Best Time to Visit

April through October. The Annapolis Sailboat Show in October is the world's largest in-water boat show.

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Annapolis Walking Tour FAQ

What are the best walking tours in Annapolis?+
Roamee Pro offers walking tours in Annapolis covering Maryland State House, US Naval Academy, City Dock, and more. Each includes narrated stories, insider tips, and hidden gems.
Is there a free Annapolis walking tour?+
Yes — Roamee Pro offers a free Annapolis walking tour with audio narration. Explore Maryland State House, US Naval Academy, City Dock, plus hidden gems like Ego Alley and Historic Annapolis walking tour, with no booking.
Is Annapolis a good city to explore on foot?+
Maryland's colonial capital on the Chesapeake Bay, with America's oldest state house and the US Naval Academy. The historic district is small and entirely walkable. Park at the Navy-Marine Corps Stadium and take the free shuttle downtown.
What are the top things to do in Annapolis?+
Top attractions include Maryland State House, US Naval Academy, City Dock, William Paca House. Roamee Pro connects these with audio narration about each stop's history and culture.
What hidden gems should I visit in Annapolis?+
Some lesser-known spots: Ego Alley, Historic Annapolis walking tour. Roamee Pro includes these off-the-beaten-path discoveries so you see what most visitors miss.
When is the best time to visit Annapolis?+
April through October. The Annapolis Sailboat Show in October is the world's largest in-water boat show.
Do I need a tour guide in Annapolis?+
With Roamee Pro, your guide is on your phone — self-guided walking tours with audio narration for Annapolis. No booking, no group, walk at your own pace.

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