Pequot Library // 1894

The Pequot Library in Southport, Connecticut was founded in 1889 by Virginia Marquand Monroe and her husband Elbert B. Monroe. The library, designed by noted New York City architect Robert H. Robertson, opened to the public in March 1894. The building is Romanesque Revival in style in a granite sandstone construction. There is an expansive roof area topped with red tile and hipped dormers; an arcaded entrance porch with three arched openings serves as the focal point of the front facade. It was Mrs. Monroe’s intention that Pequot be as “free as air to all”, which it remains as to this day.

William Bulkley House // 1767

The William Bulkley house was built circa 1767 and is one of the few extant pre-Revolution houses in Southport. In 1779, during the Revolutionary War, Fairfield and vicinity were burned and ravaged by Tory Loyalists. Only eleven houses throughout the region survived the burning; one of four in Southport was the Bulkley residence.

Paschal Sheffield House // c.1826

This Greek Revival home built c.1826, is perfectly articulated in the classical temple form. It was built for Paschal Sheffield, a well-respected member of the Southport community throughout the nineteenth century. His father was a privateer during the Revolutionary War, and moved to Southport to settle and enter in the mercantile trade business. Paschal appears to have been involved in business and local politics until his death. After his death, the home was marketed as a tear down for a new summer resort, but it was retained by future owners.

Ms. Hetty Gookin House // 1874

Warren Demman Gookin (1810-1874) was born in Haverhill, New Hampshire. He was educated at Haverhill Academy and Dartmouth College, graduating from the latter institution in 1830. In 1835 he went to Cuba where he remained for ten years as a sugar planter. Later, he was engaged in a mercantile business in Oregon, finally settling in Brooklyn, NY and working as a shipping merchant in New York City until his death in 1874. After his death, his widow Hetty moved back to her hometown of Southport, CT and built this large home. Later this was the home of Mrs Gookin’s stepdaughter, Mrs Edwin Waterman.

Pequot School // 1917

The Pequot School in Fairfield was built in 1917-18 and is one of only a few institutional buildings erected in the Southport area during the early twentieth century. The school, designed by architect William H. McLean, replaced an earlier school on the site which was built in 1854. The 1854 wood-frame school building was outgrown in the early 20th century and the school board voted to demolish the old building and replace with a larger, modern school. The school is a unique design in the Classical Revival realm, but capped with a cupola and stunning green tile roof. The school closed in 1972, and the historic Pequot School building was acquired by the Southport Conservancy as a treasured landmark. It was occupied by the town until 1985 when it was occupied by the Southport School.

Samuel Allen Nichols House // 1848

Samuel Allen Nichols (1790-1864) was born in Fairfield, Connecticut to a large family. He began his adult career as a farmer, but shifted towards the merchant trade after seeing how the village of Southport began to see massive wealth accumulating. He ran a store in the town and later became involved in local politics serving as the clerk from 1847-1863. A year after he accepted this position, he had this home built on Harbor Road. The 1848 home was Gothic Revival in style with gabled dormers, lancet windows, and decorative bargeboard. Nichols died in 1864 and the home was likely willed to one of his five living children. The home was renovated around 1871 with a Second Empire style Mansard roof and square belvedere to overlook the Southport Harbor. Since then, much of the detailing has been removed, but the home remains as a gorgeous home, changed over time to keep up with the changing architectural tastes of the 19th century.

Perry House-Trinity Church Rectory // 1832

I have a thing for temple-front Greek Revival homes, and this is no exception. This marvelous home was built in 1832 for Francis Dimon Perry (1809-1884), who inherited some of his father’s wealth and became President of Southport National Bank in town. He was a devoted member of Trinity Church throughout his life. Upon Mrs. Perry‘s death in 1893, couple left their residence to the Trinity Church to be used as the parish rectory.

Simon Sherwood House // 1884

The Simon C. Sherwood house, built in 1884, is a fine late nineteenth-century eclectic Victorian home, somewhat unique to the Southport area of Fairfield, CT, which is dominated by early-mid 19th century styles. Simon Couch Sherwood was the son of Edwin Sherwood, a wealthy shipping merchant who made a fortune from trade between New York and Savannah. The Queen Anne-Eastlake style home was added onto with a larger porch, obscuring an original oriel window on the side elevation. Sadly, the home has a safe, yet inappropriate pale yellow body color with white trim, which does not showcase the intricacies of the Victorian era home.

Edwin Sherwood House // 1837

Located next to his son’s house, the Edwin Sherwood House in Southport, Connecticut is an excellent example of Greek Revival residential architecture in New England. The home was built in 1837 for Edwin Sherwood, a sea captain who traded between New York and Savannah with his two ships “America” and “Georgia”. From this wealth, he became President of the Southport Savings Bank and Director of the Danbury-Norwalk Railroad. The home was renovated in 2017 with a modern interior by Ken Gemes, an interior designer.

Augustus Jennings House // c.1830

Walking around Southport Village in the town of Fairfield, Connecticut, transports you to an early-mid 19th century town with large Federal and Greek Revival homes overlooking Southport Harbor and the Long Island Sound. This home on Westway Road was built around 1830 for Augustus Jennings (1814-1886), the son of Captain Abraham Gould Jennings. Augustus became a carriage maker in Southport before founding Jennings Brothers, a paper manufacturing company; which in 1867, began to produce Japanese paper products. The Jennings House was originally located near the Pequot Library, but was relocated in 1899, which was likely when the central shingled gable at the roof with Palladian window was added.