John Hoyt Perry House // c.1875

John Hoyt Perry was born in Southport in 1848, and graduated at Yale in 1870. He received his professional education at Columbia Law School and was admitted to the bar in Bridgeport, CT in 1872. He had an active law career in Connecticut, later working as a judge. He served Southport in the House of Representatives throughout much of the end of the 19th century. In 1913 he was elected to the Connecticut Senate and served as the minority leader. He served as counsel for the United States in arbitration proceedings with Chile in 1902, and as counsel for the town of Fairfield. This home in Southport was constructed for him, likely around 1875 after he accepted his position as a head attorney at a major firm nearby. The home can be classified as a blending of Stick style and Queen Anne Victorian design with the asymmetrical form, tower, large porch with projecting porte-cochere, shingle siding, and bargeboards.

Southport Savings Bank // 1865

The Southport Savings Bank obtained a charter from the Connecticut General Assembly in May 1854, and was organized on September 25 of that year. Original incorporators included Paschal Sheffield, Austin Perry, Wakeman B. Meeker, Charles Perry, Prancis D. Perry, E.D. Sherwood, John Meeker, Frederick Marquand, and Andrew Bulkley. A new building, located at the foot of Main Street, was constructed to be accessible to shipowners, shop keepers, the farmer patronage, and commercial traders. This bank building was occupied in 1865, eventually merging with Bridgeport People’s Savings Bank on July 1, 1955, becoming the Southport Branch of the People’s Savings Bank – Bridgeport. It ceased to be a bank in the 2010s and is now occupied by the Southport School.

Moses Bulkley House // 1861

Constructed in 1861, this Victorian Gothic mansion in Southport, Connecticut, stands out amongst the many Classically inspired homes nearby. Designed by Bridgeport architects Lambert & Bunnell for Moses Bulkley (1796-1868), the house is designed on a cruciform plan, synonymous with the Gothic style. Expansive pointed gables trimmed with a gingerbread bargeboards, pointed arched windows, ogee arches trimmed with jigsaw tracery on the verandah, and a tall square tower topped with a steeply-pitched pyramidal roof are all seen in this beauty. If only it had a historically appropriate paint scheme to really make those details pop!

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.

Charles Perry House // c.1830

Charles C. Perry (1795-1870) was a wealthy nineteenth-century shipowner and sea captain and a prominent figure within Southport’s community. After his father’s death in 1814, when Charles was just 25, he inherited a large sum of money from his father’s will and followed his footsteps as a career. Miah Perry’s will stipulated that in order to keep the family together, members were to reside at the family home for five years from his death if neither of the daughters married; “but in case they remain unmarried at the expiration of five years…my estate shall not be divided until eight years from my decease unless one of the said daughters should marry…partition may be immediately thereafter made.” Talk about pressure to get married!

It is unclear if any daughters got married before, (Julia, one daughter died in 1821 at 22 years old). That same year, Charles Perry seemingly got his part of the inheritance and acquired the land upon which this house stands. He was then twenty-six years old and unmarried. He appears to have built it later as a blending of the Federal and Greek Revival styles, perfectly complimenting each other.

Austin Perry House // c.1830

One of the nicest examples of residential Greek Revival architecture I have ever seen is the Austin Perry House (c.1830) in the Southport area of Fairfield, CT. Austin Perry (1798-1864) was a member of a prominent merchant family, holding businesses in Fredericksburg, Virginia, before returning to Southport to manage a general store. He retired in his forties and resided at this home until his death. His home is a balanced, symmetrical design with massive Corinthian columns surmounted by a carved anthemion motif ornamenting the gable pediment.

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.