Boston started here. Charlestown was a thriving settlement a year before colonials headed across the Charles River at William Blaxton's invitation to found the city proper. Today the district's attractions include two of the most visible—and vertical—monuments in Boston: the Bunker Hill Monument, which commemorates the grisly battle that became a symbol of patriotic resistance against the British, and the USS Constitution, whose masts continue to tower over the waterfront where it was built more than 200 years ago.

The blocks around the Bunker Hill Monument are a good illustration of how gentrification has changed the neighborhoods. Along streets lined with gas lamps are impeccably restored Federal and mid-19th-century town houses; cheek by jowl are working-class quarters of similar vintage but more modest recent pasts. Near the Navy Yard along Main Street is City Square, the beginning of Charlestown's main commercial district, which includes City Square Park, with brick paths and bronze fish sculptures. On Phipps Street is the grave marker of John Harvard, a minister who in 1638 bequeathed his small library to the fledgling Cambridge College, thereafter renamed in his honor. The precise location of the grave is uncertain, but a monument of 1828 marks its approximate site.

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