The short brick-paved spine of historic Annapolis, running four blocks downhill from St. Anne's Church to the City Dock. Despite the name, it has never been wider than two lanes — its narrowness is part of the colonial-era charm. The street is lined with independent shops, art galleries, taverns, and several of the most photographed Federal-period storefronts in the country.
A handful of properties date to the 18th century, including the Middleton Tavern (1750) at the foot of the street, where Washington, Jefferson, Franklin and Madison all dined. The 200 block, with its uneven rooflines and tile-and-brick mix, gives the best sense of how the working town would have looked when ships still sailed up to the dock. Closed to vehicles for festivals and events through summer.