Pomeroy-Belden House // c.1758

This stunning gambrel-roofed Georgian manse is located on Bronson Road in Fairfield’s Greenfield Hill neighborhood, a well-preserved in the northern part of town with large historic homes on large lots. The Pomeroy-Belden House was built in about 1760 for Seth Pomeroy (1733-1770), the son of Seth Pomeroy Sr. (1706-1777) a gunsmith and soldier from Northampton, Massachusetts, who served in King George’s War, the French and Indian War, and the Revolutionary War (at nearly seventy years old). Seth Jr. graduated from Yale in 1753, and would accept the call as the minister of the Greenfield Hill Congregational Church from 1757 until his death in 1770. He had this stately house built for his family during his time as minister. After his death, the house was purchased by Captain David Hubbell who used it as a store until it was purchased by Reverend William Belden, who served as pastor of the Greenfield Hill Congregational Church from 1812-1821. The Georgian mansion features a central double-door entry with traditional door surround, later shingle siding and a gambrel, wood shingle roof punctuated by three small dormers.

Greenfield Hill Congregational Church // 1855

Local residents of northern Fairfield successfully petitioned the General Assembly to establish a Congregational church in 1725 as a new Northwest Parish, a distinct group from the Fairfield Congregational Church. Their first meeting house was erected just years later in 1727. A larger, more substantial meetinghouse was built in 1760. The area of Greenfield Hill has always been remote and more suburban, but became important in the late 18th century when Timothy Dwight became minister of the Greenfield Hill Congregational Church in 1783. Dwight would go on to become the eighth president of Yale College (1795–1817). With increased funds and affluent members, another church was built in 1850 from plans by esteemed architect Richard Upjohn, in the Gothic style. Sadly, just years after it was completed, a fire from a furnace inside destroyed the church. So again, they rebuilt in 1855 with the building we see today, sort of. Architect Alfred Nash furnished plans for the building which was more Italianate in design. The church would be modernized in the 1940s in the Colonial Revival style, from plans by local architect Cameron Clark, likely inspired by the collection of Colonial-era homes nearby, including his own home in Greenfield Hill. The church remains a visual anchor for the affluent neighborhood.

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.