The original settlement of the Puritans was named after the king they left behind. A swampy mess of a place without much access to fresh water, Charlestown was eventually abandoned when John Winthrop and the gang were invited over to the Shawmut Peninsula to found Boston.

Charlestown, which is incorporated as a neighborhood of Boston, grew to be an important port in the 18th century. Then tragedy struck during the Revolutionary War, when the British fired cannonballs filled with incendiary oil across the channel and burned the city to the ground as a retaliation for their losses at the Battle of Bunker Hill.

Charlestown was rebuilt in the early 19th century, about the same time as the brick mansions and brownstones were going up on Beacon Hill, and it shares a similar colonial feel with that neighborhood. Gas lamps, black shutters, and window boxes give an antique feel to much of the neighborhood, especially in the area around Monument Square, at the top of the hill surrounding the Bunker Hill Monument.

In the 20th century, the area became home to an Irish working-class community known by the rest of the city as “townies.” They still come out to celebrate on Bunker Hill Day, a special neighborhood holiday to commemorate the battle.

Charlestown has changed in recent decades, as young professionals priced out of Beacon Hill and the Back Bay in the 1980s descended upon its quaint streets and carved its townhouses into thousands of luxury condos. Boutiques and gourmet restaurants sprang up to serve the new crowd, giving the neighborhood a feel similar to Georgetown in Washington, D.C. The isolation of the enclave gives its residents, whether recent arrivals or townies, a sense of community few other neighborhoods match.