Wakeman Memorial Building // 1913

The Wakeman Memorial Building in Fairfield, CT, is one of a few buildings erected in the Southport area during the early twentieth century. The boldly proportioned central portico is supported by square Tuscan columns with an Ionic fretwork entablature and denticulated cornice, and topped by a spindled parapet and an elliptical shaped Palladian window on the second story. The red tiled gambrel roof, splaying beyond the exterior walls, is bracketed by decorative modillions. The building was constructed in 1913 through funds by Miss Frances Wakeman in memory of her grandfather, Jesup Wakeman, at a cost of fifty thousand dollars. The building was used by the Boys and Girls Club of Southport as a club house, offering sewing classes, a reading room, and offices. The building was converted to a home after the Boys and Girls Club moved to a larger facility.

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.

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.

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!

Osborn House // 1772

This homestead in Fairfield, Connecticut is situated on the edge of what was formerly called Pequot Swamp, and was originally built by Stephen Osborn in 1772. It is said to be the third Colonial dwelling erected in this part of the town and was left undisturbed by the British when they burned Fairfield in 1779 and raided various sections of the country along the shore. The home was originally located a few blocks away, but was moved in the 1950s when the highway (I-95) was routed through this part of Fairfield. The saltbox Georgian home was documented prior to the move by the Historic American Buildings Survey (HABS).

David Ogden House // c.1750

This saltbox house was built by 1750 for David Ogden at the time of his marriage to Jane Sturges. For the next 125 years it was home for the Ogden family in the farming and coastal shipping town of Fairfield. The home was sold out of the family in 1839 to Henry W. Banks, who continued to farm on the nearly 75 acres of farmland. By the 1920s, the home was suffering from deferred maintenance and was at risk of demolition. Luckily, Annie Burr Jennings (1855-1939), a philanthropist who was born into a wealthy family, sought to give back to her town. Jennings was instrumental in establishing and supporting a number of important community institutions, including the Fairfield Historical Society (now the Fairfield Museum) and the Fairfield Public Library. In 1931, she purchased the old Ogden Farmhouse from absentee owners and helped fund its restoration. The early saltbox vernacular Georgian home today is maintained by the Fairfield Museum and the Greenfield Hill Village Improvement Society.