Note: a separate Freedom Trail walking tour includes selected sites in Charlestown and the Navy Yard.

With its long and storied history, Charlestown is a rich architectural destination, particularly for lovers of 19th-century design.

Surrounded by rivers and bay, Charlestown was shaped by water from its earliest days. The 1629 settlers blamed brackish water and the general aspect of Charlestown for the sickness and death that beset their population. When the Rev. William Blackston invited them to join him across the Charles River on the Shawmut peninsula, promising abundant fresh springs, many readily agreed. With a better water supply, Charlestown might have remained the capital of the Massachusetts Bay Colony.

The small group that stayed in Charlestown prospered, perhaps benefiting from the reduced demand for water. By 1650 Captain Edward Johnson described a thriving town: “It hath a large market-place near the water side built round with houses, comely and fair, forth of which there issues two streets orderly built with some very fair houses, beautified with pleasant gardens and orchards.”

Prior to their 1775 departure the British burned most of the town, resulting in a loss of more than 500 pre-Revolutionary houses, barns, mills, and shops. Its citizens returned and began rebuilding following the war, and Town Hill, Main Street, and Winthrop Square have prodigious concentrations of late Georgian and Federal dwellings. Monument Square is a showplace of Victorian architecture. The Navy Yard preserves more than two centuries of the nation’s naval history. And of course, important Revolutionary War sites are featured on the Freedom Trail here.

Charlestown was annexed by Boston in 1874, a part of the same movement that also added Roxbury, Dorchester, West Roxbury, and Brighton to the capital city. Following several decades of significant gentrification (with more to come), Charlestown is vibrant and diverse neighborhood today.

The Charlestown Preservation Society works to protect historic architecture and landscapes, advocate for preservation, guide responsible development, and educate people about the unique character of the community. See to learn about programming including house tours.

Image: ©Bruce T. Martin. All other rights reserved