Simon Couch Sherwood (1845-1906) of Southport was the son of Edwin Sherwood, a wealthy shipping merchant involved in the trade between New York and Savannah. Simon C. Sherwood is described in the Commemorative Biographical Record of Fairfield County, Connecticut (1899):
Aside from his investments, he is living retired, in the enjoyments of a well-regulated life. On October 14, 1868, Mr. Sherwood was married to Miss Matilda Simpson, of Southport, daughter of John Simpson, and two sons—Simon W. and Richard S.—have been born to them. Mr. and Mrs. Sherwood are identified with the Congregational Church, and he is a member of the executive committee of same. In his political preferences he was once a Democrat, but for some years past has been a Republican. He is a trustee of the Southport Savings Bank. Mr. Sherwood’s honorable business methods and his upright life have gained for him prestige in the community where he has so long made his home, while his genial manner enables him to make friends easily, and when once a friendship is won it is always his. He is a member of the Sons of the American Revolution.
Sherwood’s house, built in 1884 at 67 Westway Road in Southport, features an eclectic mix of Victorian-era stylistic elements. After his death in 1906, the house continued as the residence of his widow and his son Simon Wakeman Sherwood until 1916.
The house at 35 Rose Hill Road in Southport was not always a house. It was built in 1912 by the Southern New England Telephone Co. as its Southport Telephone Exchange. The business office was on the first floor and the telephone switchboard operations were on the second floor. The Telephone Exchange moved to reef road in 1947 and the 1,722-square-foot building was converted to residential use. For a time it was divided into two apartments until recent owners returned it to being a single-family home. The property also has a guest house that was once a four-bay garage used by SNET.
At 494 Harbor Road in Southport in the town of Fairfield is a Gothic Revival house built in 1848 for Allen Nichols, who was in the dry goods business. The house was later remodeled in the Second Empire style and had a cupola, since removed. Nearby are two other houses built by members of the Nichols family.
Mrs. Benjamin Pomeroy, the wife of a shipping merchant, had the house at 658 Pequot Avenue in Southport erected for herself and her daughters. The Second Empire-style house, which features an elaborate front porch and mansard roof, was designed by the architectural firm of Lambert & Bunnell. Constructed in 1868-1869, the house’s builder was Gamaliel Bradford of Fairfield. The house remained in the family until 1946. The house’s carriage house was erected around the same time as the main house.
According to his obituary in The Bankers’ Magazine, and Statistical Register, Vol. 38, No. 11 (May, 1884):
Francis D. Perry President of the Southport (Conn.) National Bank, died after a short illness in that town on April 16th, in his seventy-fifth year. He had been for over thirty years an officer of this bank, and of its predecessor, the Southport Bank. He was also for some years Secretary and Treasurer of the Southport Savings Bank, and to these institutions devoted his energies with fidelity, perseverance, and marked ability. Mr. Perry was a man who won, by his high personal character, universal respect and regard. Thoroughly conscientious, decided in his opinions, but courteous, considerate and liberal, he exemplified the best type of the faithful official and the Christian gentleman. The boards of directors of the two banks, at a special union meeting, passed unanimously a series of resolutions expressive of their high regard and appreciation of the deceased.
Perry’s Greek Revival house, at 678 Pequot Avenue in Southport, is similar in design, with a five columned front portico, to his brother Henry Perry’s house at 45 Westway Road in Southport. They may have been designed or built by the same person. Perry was a member of Trinity Parish and after his widow died in 1893 the house was left to the parish as a rectory.
Trinity Episcopal Church in Southport was built in 1862. Eight years later the parish began to consider plans to build an adjacent chapel that would serve as a Sunday school. The Parish School opened on September 23, 1872 in the new Carpenter Gothic-style Chapel, which features board-and-batten siding. Originally a free-standing structure, the Chapel, which now serves as a parish hall, has been connected to the church complex through twentieth-century additions.
The Wakeman Boys & Girl Club was founded in 1913 by Miss Frances Wakeman (1835-1918) of Southport. She was the granddaughter of Jessup Wakeman, who settled in Southport in the early nineteenth century and became a well-known merchant, and the daughter of Zalmon Bradley Wakeman, a successful businessman who left a large property to his family at his death in 1865. A description of Frances Wakeman and of the club she founded can be found in Volume II of the History of Bridgeport and Vicinity (1917):
Miss Frances Wakeman was reared to womanhood in her native town of Southport, where she has spent her entire life. Her beautiful home, Rose Hill, which commands a view of Long Island Sound and surrounding sections of Southport, is one of the most attractive places in this part of the state. Miss Wakeman is a lady of innate culture, possessing refined taste and artistic temperament. She is one of the best known women of Fairfield county and she takes a most active and helpful interest in the public affairs of the village of Southport and its institutions. This was manifest in the beautiful gift which she and her cousin, Miss Crapo, made to the people of Southport. The gift was a red brick building known as the Wakeman Memorial and erected in memory of their grandfather, Jesup Wakeman, at a cost of fifty thousand dollars, to be used by the boys and girls of Southport as a club house. The building is maintained by Miss Wakeman and in it are found a reading room, a sewing room and rooms for dancing and recreation where the boys and girls may find entertainment amid delightful and beneficial surroundings. Instruction is given to the girls in sewing and dancing is also taught. This building was opened in 1913 and it contains a bronze tablet on which is engraved the following: “The Wakeman Memorial, 1913. This building was erected and equipped for philanthropic work with funds contributed by Frances Wakeman and Cornelia Wakeman Crapo. Their grandfather, Jesup Wakeman, is remembered in its name. On Christmas day of 1913 it was opened to the youth of Southport in the hope that its privileges would enable and persuade them to grow up worthy in the community which the donors love, regardless of circumstances or creed. Their welcome here depends alone upon the regard they show for that which the place provides.”
Among the new buildings that our workers have not had an opportunity of visualizing is the Wakeman Memorial at Southport, Conn. The accompanying illustration shows the front elevation overlooking the Long Island Sound. The basement provides accommodation for industrial classes, and the two floors above are divided into reading, game and club rooms, together with a kitchen and living quarters for the Superintendent. The extension at the rear is the gymnasium. This building was erected and furnished throughout by Miss Wakeman. Securities were also set aside for the permanent endowment of the work. Southport is a village with few industries, therefore this building not only serves the boys, but is made the center of quite an extensive community work. Dr. George W. Phillips is the Superintendent.
The Wakeman Boys & Girl Club has since moved out of its original home, which is now a private residence. The building was photographed for the Historic American Buildings Survey.