Annapolis was built long before the car, and it shows in the nicest way. The historic downtown is compact enough that almost everything sits within a gentle stroll of everything else, from the brick shopfronts of Main Street to the masts crowding the harbour.
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Start at the top of Main Street
Main Street slopes gently down towards the water, and taking it from the top is the best way to get your bearings. Independent shops, cafés and restaurants fill the old brick buildings on either side, and there’s a window worth pausing at every few steps. At the bottom, the street opens onto City Dock, where boats nudge their moorings and there’s always something coming in or heading out. The benches there are made for a slow coffee, and we’ve lost more time on them than we’d care to admit.
Where the war with Britain officially ended
Back up the hill, the streets curve round to the Maryland State House. It was finished in 1779 and still houses Maryland’s legislature, which makes it the oldest state house in America in continuous legislative use. Its story carries a particular resonance for British visitors. This is where George Washington resigned as commander-in-chief, and where the Treaty of Paris was ratified, formally bringing the War of Independence to a close.
Old houses and a hidden garden
Maryland Avenue leads away from the State House, past more small shops, to the Hammond-Harwood House. Built in 1774, it was the final work of architect William Buckland, and its carved front doorway is worth a long, slow look. A few streets away, the William Paca House and Garden was home to one of the signers of the Declaration of Independence. Behind it, out of sight from the street, lies a restored two-acre garden that feels miles from the town around it.
Galleries, then over the water to Eastport
Around Church Circle, West Street is the heart of the Annapolis Arts District, with galleries tucked between restaurants. For anyone with a little more walking in them, the Spa Creek bridge leads over to Eastport. It’s a quieter, easygoing neighbourhood where restaurants sit right on the water and the view looks back across the creek to the old town.
Somewhere to stay, right in the heart of it
Staying downtown is what makes all of this effortless, because every day starts at the front door. The Historic Inns of Annapolis bring together three historic buildings on State Circle: the Maryland Inn, the Governor Calvert House and the Robert Johnson House. Each is a short stroll from Main Street and the water. The Governor Calvert House takes its name from Charles Calvert, Governor of Maryland in the 1720s, and looks straight across the circle to the State House.
For those who would rather wake up to the water, the Annapolis Waterfront Hotel sits on the harbour itself. Part of Marriott’s Autograph Collection, it has rooms looking out over the boats and two restaurants on site, Marmo and Armada. Main Street is a few minutes’ walk away.
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Park the car when you arrive, and it can happily stay there until it’s time to head home.Visit www.visitannapolis.org to discover more and start planning your next trip to Annapolis, visit
www.visitannapolis.org
Posted by: Visit Annapolis & Anne Arundel County
Posted on: 22/10/2026