Charlestown

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 she was built more than 200 years ago.

As a neighborhood, Charlestown remains predominantly Irish-American, although gentrification that began in the 1980s continues. Today, despite the inroads made by trendy restaurants such as Todd English's Olives and chic digs such as the Navy Yard condos, the area still suffers a bit from its reputation as an alleged home turf for Irish-led organized crime. A number of bloody murders that remain unsolved—because of the neighborhood's vaunted "code of silence"—haven't helped. But Townies (as old-time Charlestown residents are called) are fiercely proud of their historic, well-maintained streets.

The blocks around the Bunker Hill Monument are a good illustration of a neighborhood in flux. 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. Nearby Winthrop Square also has its share of interesting houses. 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 young 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.

To get to Charlestown, you can walk across the Charlestown Bridge from the North End, or take Bus 93 from the Haymarket T station; it stops three blocks from the Navy Yard entrance. A more-interesting and speedy way to get here is to take the MBTA water shuttle from Long Wharf in downtown Boston, which runs every 15 or 30 minutes year-round.

A Good Walk

If you chose to hoof it to Charlestown, follow Hull Street from Copp's Hill Burying Ground to Commercial Street; turn left on Commercial and, two blocks later, right onto the bridge. The entrance to the Charlestown Navy Yard is on your right after crossing the bridge. Just ahead is the Charlestown Navy Yard Visitors Information Center; inside the park gate is the USS Constitution and the associated USS Constitution Museum. From here, the red line of the Freedom Trail takes you to the Bunker Hill Monument.

Timing

Give yourself two to three hours for a Charlestown walk; the lengthy Charlestown Bridge calls for endurance in cold weather. You may want to save Charlestown's stretch of the Freedom Trail, which adds considerably to its length, for a second-day outing. You can always save backtracking the historic route by taking the MBTA water shuttle, which ferries back and forth between Charlestown's Navy Yard and downtown Boston's Long Wharf.