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The best shopping in Annapolis isn't in the malls — it's on the streets. From vintage stores to artisan workshops, spots like City Dock and William Paca House are scattered through neighborhoods that reward the curious walker. Wander further and you'll stumble on Ego Alley — the kind of find you can't replicate online.
Maryland's colonial capital on the Chesapeake Bay, with America's oldest state house and the US Naval Academy.
Roamee Pro, also known as Roamee, offers a free self-guided shopping tour route in Annapolis. The audio walking tour can include stops such as City Dock — the harbor-front heart of downtown with restaurants, shops, and sailing vessels, William Paca House — a restored 18th-century Georgian mansion with elaborate gardens, plus hidden gems like Ego Alley — the narrow inner harbor channel where boaters cruise to show off their vessels, a local spectacle and Historic Annapolis walking tour — the compact colonial downtown has more 18th-century brick buildings per square mile than almost any US city.
Use this page as a starting point for a Annapolis walking tour, a free self-guided route, or the Roamee app for Annapolis. Roamee Pro keeps the route flexible so you can follow the stops, skip ahead, or explore nearby streets at your own pace.
Visitors explore Annapolis for history and coastal walks, but every walking route ends up passing through City Dock and William Paca House and neighborhood markets that tell their own story about the city. Don't overlook Ego Alley — it reflects what the people of Annapolis actually buy, make, and value.
The historic district is small and entirely walkable. Park at the Navy-Marine Corps Stadium and take the free shuttle downtown.
April through October. The Annapolis Sailboat Show in October is the world's largest in-water boat show.
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