Located on the spot of the founding of Charlestown in 1628, City Square Park occupies land where John Winthrop, the first governor of Massachusetts, built his home. Kept as an open square for much of the early part of the nation’s history, several arterial roads converged on this space by the 1950s. In order to restore the open character of the space, beginning in the 1970s, the Central Artery North Area project moved all of the main roads into tunnels under the site. This project was the predecessor to the Big Dig. 

As a result of removing the main roads, the space was completely redesigned in the late 1980s and early 1990s. Halvorson Design Partnership was contracted to renew the space and later won a Boston Society of Landscape Architects Merit Award for their work. The design incorporates a broad range of plant varieties, while keeping a brick and granite hardscape palette, which enables a smooth transition between modern park and the surrounding historic neighborhood.

The four gateways into the park honor historical Charlestown figures, with the original location of Winthrop’s house outlined in the lawn with stone, while a memorial in honor of World War II soldiers stands to one side. The central plaza space of the park is marked by a fountain surrounded by curved seat walls and bronze sculptural elements. During the summer months, movies are shown on the lawn.

Another stop along the Freedom Trail, this park is also along the Harborwalk and can be reached by walking from Community College or North Station, or by taking the number 92 or 93 bus from Haymarket or Sullivan Square Station.