Main Street Historic District

The Main Street Historic District comprises five residential properties along United States Route 1, with three positioned on the north side and two on the south. All buildings display Italian-influenced architectural features and design elements tied to 19th-century maritime life.

These houses were built between 1860 and 1875 by prosperous sea captains who wanted to display their wealth and establish a new residential area. They mark a period when maritime trade brought significant prosperity to the region.

The homes display design choices that reflect how successful maritime traders wanted to present themselves and their families to the community. These houses show how wealth from shipping shaped the way people built and decorated their living spaces.

The district stretches from Black Road to Navy Street and is easily walkable to view the houses from the street. Best explored during daylight hours when you can clearly see all the architectural details on the facades.

The McGilvery House stands out with its three-story wooden construction topped by a mansard roof decorated with pedimented dormers and detailed cornices. This house represents one of the most elaborate examples of construction methods from that era in the area.

Location: Middletown

GPS coordinates: 41.56300,-72.64800

Latest update: December 14, 2025 09:40