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.

Mary Pomeroy House // 1868

Mrs. Mary Pomeroy, the widow of one of Southport’s industrious and wealthy shipping merchants, Benjamin Pomeroy, built this large residence for herself and her daughters, soon after her husband’s death. Mr. Pomeroy was a merchant who also served as a Senator. In 1866 with ailing health, he took a doctor on a private ship to try various remedies in the West Indies, to no avail, he died at 48 years old. Ms. Pomeroy appears to have taken the money her and her husband had saved and built a large mansion to cement her position in town as the most eligible bachelorette in town. While she never remarried, she sure showed the town what good taste looks like! The facade of the Pomeroy house is symmetrical with a projecting three-story central pavilion, all surmounted by a mansard roof with cresting. Rounded dormers with twin round-headed windows pierce the roof’s multicolored slate surface, making this Second Empire house one of the nicest in a town full of historic homes!

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.

Trinity Church, Southport // 1862

The Trinity Episcopal Church in the Southport section of Fairfield, Connecticut was established in 1725. Twenty families met for worship at its first meeting house in the center of town on Thanksgiving Day, 1725. Since then, the church has constructed five different places of worship in locations around town. Architect Albert C. Nash designed the church which was constructed during the years 1854-56. Sadly, the building’s near total destruction by wind during a tornado on January 1, 1862, required the church to be completely rebuilt as originally planned, with a few structural alterations. Trinity Church is an excellent work of early Gothic Revival church architecture in wood, one of the best I have seen in my trips around the region.

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.

Southport Railroad Stations // 1884 & 1895

The Southport railroad stations in Fairfield, Connecticut, are reminders of the important role of railroad passenger service in the historical development of the town which continues to this day. In Southport, there are two stations, an east-bound and west-bound, one on either side of the tracks. The older east-bound station was built in 1884 to replace a depot destroyed by fire. It is typical of the substantial brick stations built at small-town stops throughout the state in the period. The use of brick was likely to prevent fire destroying yet another station. The stations were commonly large enough to accommodate spacious waiting rooms, ticket counters, offices, restrooms, and a baggage area. The brick station was converted to a restaurant, with a modern addition by Roger Ferris + Partners completed by 2017.

The wooden west-bound station was built around 1895 as part of a massive rebuilding of the New York, New Haven and Hartford Railroad’s main line. At this time, the railroad adopted a single design-concept for all the stations, reverting to wood construction, and limited the stylistic details. The Southport station has an interesting design however; with its saltbox-like roofline, bargeboards, and stick detailing. Imagine all the people and stories that passed through these buildings. Parents saying goodbye to children going off to college or war, businessmen and women commuting to and from work, or people like me who took it to Manhattan!