The Southport Historic District was listed on the National Register of Historic Places in 1971. Portions of the content on this web page were adapted from a copy of the original nomination document. [‡]
Significant Buildings in the Southport Historic District
750 Harbor Road — This is an imposing Greek Revival house with four Doric columns supporting the pedimented central block of the structure. Oliver Perry was a substantial citizen: he established his fortune as a shipowner and a merchant and was Treasurer and Director of the Southport National Bank. He was active in civic affairs and served as speaker of the house of the Connecticut General Assembly and commissioner to survey and settle the border dispute between Connecticut and New York.
780 Harbor Road — This is the residence of Walter Perry III. It is a Federal style house built in 1830 along the simpler lines of late 18th and earlier 19th century.
712 Harbor Road — Residence of W.S. Cargil. This house was built in the 1830's. Greek Revival in style, the elaborate Corinthian columns and decorated pediment distinguish it as a fine example of the craftsmanship and architecture of the time. The original home had four square rooms on each floor, but additions were made within the 40 years to the back of the house to provide more space.
478 Harbor Road — Residence of W.W. Payson. This mansion was built in 1831 by William Webb Wakeman on what was formerly Rose Hill Road in the area of the Rampasture which was undivided common land extending from the top of Rose Hill to the Harbor. Wakeman was a prosperous and successful man whose shipping interests were so wide and diverse that it could almost be said that they constituted an empire. His business grew from participation in the coasting trade between New York City, Salem, and Boston to the ownership of a line of steamships which during the civil war were almost exclusively employed as government transports for men and equipment.
72 Willow Street — Residence of Mrs. James Truslow Adams. Paul King Sheffield who was a privateersman operating out of New London and Stonington built this house in 1796. It was the childhood home of Joseph Sheffield a self-made man who established a great fortune through commercial activity and construction work and who built among other things the Rock Island Railroad.
104 Old South Road — This house was built by Joseph Sheffield's brother Paschal Sheffield who was a privateer for the government of Argentina between 1812 and 1825 in its struggle for independence against Spain.
824 Harbor Road — Residence of Frank D. Wendt. Built prior to 1766, this is the one house on the harbor in Southport that is known to have escaped the burning in 1779. William Bulkeley the original owner was a storekeeper. Later the house was purchased by Wakeman B. Meeker of the firm of Meeker and Sherwood, shippers who carried freight and passengers out of Southport on a regular basis
The Meeker House is 2-1/2 stories with a large central chimney and a huge fireplace with a Dutch oven. It has a plain pitch roof; the sides were covered with hand-hewn shakes. Most of the south side of the house still has the original shakes fastened with hand-wrought nails. Recently the shutters have been removed, from the front of the house and the windows have been restored to their original 12 over 12 small panes. While the age of the barns and outbuildings is not known, they, too, are early as can be seen from their internal construction and since the deed conveying the house in 1809 refers to the "barn and chaise-house," it is probable that they are at least of that date.
25 Westway Road — Residence of Sherwood L. Pratt. This typical mid-19th century village house, with its porch across the front and part of two sides, its long windows on the ground floor, and its "gingerbread" trim, was built in 1856 by Wakeman Meeker, Jr. The particular pattern of trim has been widely used on other houses in Southport. The two large maple trees on the east of the house were planted as "bride and groom" trees at the time the son married and moved into the house. The only exterior change in the house since it was built has been the addition of two windows in the gable ends.
95 Westway Road — Residence of Mrs. J.W.C. Bullard. This house was built in 1840 by Edwin Sherwood, a younger brother of Simon Sherwood, the partner of Wakeman Meeker. Edwin Sherwood was the owner of the brigs "America" and Georgia," engaged in the trade between Savannah and New York. A substantial citizen, he was a president of the Southport Savings Bank and a promoter and director of the Danbury-Norwalk Railroad.
564 Harbor Road — Residence of John A. Millington. This fine house was built in 1835 by another shipowner and sea captain, Charles C. Perry. It has the classic Greek Revival lines typical of the period in the latter part of the 19th century when the then owners, disregarding the total effect, installed a two-story bay window on the south side of the front of the house, thus completely changing its appearance. In 1926 new owners removed this bay window and restored the house to its present appearance. Notable on the land surrounding the house are the large trees, especially the huge beech tree.
The Bulkeley Houses: 14 Westway Road, Residence of T.I.H. Powel; 104 Main Street, Residence of Mrs. T. Maytham; 142 Main Street, Residence of C. Brophy; 114 Westway Road, Residence of Mrs. Homer Jewitt; 892 Harbor Road, Residence of William D. Crane. — Outstanding in the sea-faring community of Southport was the firm of E. Bulkeley & Sons. Eleazar Bulkeley born in Southport in 1763 was the son of James Bulkeley, a weaver who was descended from Reverend Peter Bulkeley who was one of the founders of Concord, Massachusetts. Eleazar, determined on a more active life, started going to sea at the age of 12. By the time he married and settled in Southport, he had acquired a wide knowledge of the world, of the ways of trade and shipping, and of ports on the coast of the United Sates and the West Indies. His first venture in partnership with Miah Perry of Southport did not last, but subsequently with the exercise of sound judgement coupled with a knowledge of markets he developed an extremely profitable merchant shipping business, with its head office in New York. His six sons were associated with their father in business. Jonathan, whose diary kept faithfully from 1602 until his death in 1859, chronicles events in Southport during those years and is an invaluable record, lived at what is presently 892 Harbor Road. The house, much altered, commanded a view of the harbor and Long Island Sound. The houses at 104 and 142 Main Street were built for Moses and Charles Bulkeley, in the first quarter of the 19th century. They were the same in appearance when built, though each has had some alterations. The house now at 14 Willow Street was built somewhat later by Lot Bulkeley. The house of Andrew Bulkeley stood at the corner of Harbor Road and Old South Road, across Old South Road from 692 Harbor Road. It was taken down years ago, George Bulkeley retired from the business in the 1850's and moved to Southport, and built a house at 114 Westway Road.
187 Westway Road — Residence of Clarence A. Earl. The original house was built for William Burr Dimon. Since the records show that William Dimon died in 1818 the construction of the house is prior to that date. When built it was a saltbox, with a small one-story portion on the east containing the kitchen fireplace with a beehive oven. The house has been enlarged and changed. The main section was raised to three stories, dormers were added. The kitchen wing was made into a full-size room, then it was raised to two stories. A large porch has been added in the rear, and French windows have been installed.
The enormous "Dimon Oak" in front of the house is known to be at least 260 years old. It stands nearly 100 feet tall and measures 19-1/2 feet in circumference 4 feet above ground level.
95 Main Street — Residence of John B. Zellers. Built about 1827 as an Academy, this house has also served as a place of worship and as a "town hall." The first Episcopal Church service was held here in 1828, and during the years when the Borough of Southport was in existence, the regular meetings of the Wardens and Burgesses of the Borough were held at this Academy. When Southport outgrew the building and built a new school in 1854, the building was sold at auction, but the school board preserved the bell and bell rope — and the bell is installed in the present Pequot School. Since 1854 the house has been moved closer to Main Street and substantially altered.
450 Harbor Road — Residence of Lawrence Sidebottom. This house was built in East Haven, Connecticut by Samuel Bradley in 1715. In 1945-48 it was moved and reconstructed on its present site. It is a fine example of early Connecticut salt-box architecture. The broad chimney rises from behind the ridgepole. The exterior siding is part of the original house. The bull's eye glass in the front door is of special interest.
155 Rose Hill Road, Residence of Sidney G. Talbot; 494 Harbor Road, Residence of William K. Meyers; 534 Harbor Road, Residence of Grafton Pyne, Jr. — These houses are grouped together as "Nichols" houses for at the time they were all owned by members of the Nichols family. The house at 534 Harbor Road was built in the 1780's and in 1836 was owned by Captain Sturges Nichols; a substantial amount of renovation was undertaken in the early 1950's to restore the house to its original appearance. The house at 494 Harbor Road was built about 1850 by A. Nichols. Originally it had a small cupola on top; this has been removed, but otherwise the house remains as it was built. The house at 155 Rose Hill Road has a plain pitch roof which replaces the original mansard roof.
658 Pequot Road, Residence of William N. Wallace; 418 Harbor Road, Residence of E.C. Ricotta; 385 Harbor Road, Residence of Alex R. Thompson — These three Victorian houses were built between 1855 and 1865 or 1870. They are grouped together as good examples of the period. The house at 658 Pequot Road was built in 1861-63 for Benjamin Pomeroy, who died before it was completed. The builder was Gamaliel Bradford, a master carpenter of Fairfield. It is a fine example of the Second Empire style with a mansard roof and well-designed ornamentation over the windows. The house at 418 Harbor Road appears to have been built around 1857. It was designed by the firm of Lambert and Bunnell of Bridgeport and retains its original outward appearance, although many changes have been made on the inside. The house at 385 Harbor Road was built about 1854 and was later owned by the Curtis family which altered the interior and exterior of the house considerably. Extensive remodelling was done in 1920 and about 1940.
176 Main Street — Residence of F.R. Lack. This Victorian house is of a style that is a little later than the houses previously mentioned, was built about 1875 by Oliver Bulkeley. In the 1920's it became the Pequot Inn, but in 1957 it reverted to its original use as a private residence.
45 Westway Road — Residence of Thomas Robinson and 678 Pequot Road, Trinity Episcopal Church Rectory. These houses are unusual because though built in the Greek Revival style popular in the 1830's, each has five columns in front instead of four, and both have matching pilasters against the exterior wall.
798 Harbor Road — Residence of Philip H. McLaughlin. In the 1850's Augustus Jennings had a store here and from later evidence and descriptions, the store building in existence in the 1850's now constitutes the main part of the structure that is now a residence. In 1894 the building was converted into a clubhouse for a local club which bore the intriguing name, "Bachelor's Comfort and Married Men's Relief," and for some years it was the headquarters for at least a part of the social life of Southport. During World War I it was the headquarters for British War Relief activities; thereafter, when Pequot Yacht Club was organized, it became the first clubhouse for the Yacht Club.
95 Harbor Road — Tide Mill Building. The building was the site of a grist mill from around 1722 until about fifty years ago. Although the mill buildings have been incorporated into the present structure remodelling has radically altered both interior and exterior.
668-670 Harbor Road — Jean Allen, Gift Box and The Ivy Shop. Town records indicate that the larger building at this address on the corner of Harbor Road and Main Street was built in 1834. At least a portion of it may be older, since there is in existence a rough sketch of the "Early Homesteads of Southport" which indicates that a house at this location belonged to Miah Perry who died in 1814. Internal evidence of the existing structure itself shows that the upper portion of the building is different and probably older than the ground floor. The building has been utilized as a house, a meat market, and a post office with a reading room on the second floor.
62 Center Street — Residence of Mrs. Robert Sheddan. Intimately connected with the history of Southport is this charming Greek Revival house. The Doric columns that graced the small portico were removed many years ago, but the scale and proportion of the main section of the house are excellent. It was built in 1837 by Julius Pike one of the nine sons of Molly Pike an energetic and resourceful innkeeper of the post-revolutionary period. The Doric columns of the small portico were removed many years ago, but the main section of the house retains its fine proportions. Julius Pike who built the house was in the trading firm of Pike and Sturges, who owned the sloop James K. Polke and the Schooner Empire. The former engaged in the market trade with New York while the latter was employed in West Indian commerce.
720 Pequot Avenue — Pequot Library. In 1894, the Greek Revival mansion that had been the home of Frederick Marquand since it was built in 1832, was razed. In back of it there had been under construction for several years the handsome Romanesque building that is now Pequot Library. Robertson, who designed the building, was one of a group of "avant gard" architects in New York, and the Romanesque style adopted for the Library was now seen by the public for the first time, and the Library was — in 1894 — eminently "modern."
The Library was built as a memorial to Frederick Marquand by his niece, Mrs. E. Monroe and her husband. Frederick Marquand established his fortune by creating a successful jewelry-silversmith firm in New York in the first half of the nineteenth century.
In the preceding paragraphs specific mention has been made of about one-fifth of the houses and other buildings of the more than 150 structures within the Southport Historic District. However there are many other that merit comment, such a 52 Main Street — the "Crooked House," now the residence of Julian Dedman; 139 Main Street, the residence of Richard Joyce Smith, which was built in the 1870's by Charles Gilman, and is a good example of the Victorian house of that period; 298 Harbor Road, the residence of Mrs. Norton Sturges, a charming cottage built by Captain Ward Bulkeley in 1831 that retains its original appearance and in back of which is another of the few remaining towering oaks that were once a feature of the area; and 204 Harbor Road, until recently the residence of Charles Parks, which is an early house that is possibly unique because it was built by a ship's carpenter.
The Southport Historic District is significant because it has been the center of trade and commerce in Fairfield and because its history is typical of the development of commercial life in many New England ports in the fifty years following the revolutionary war. The architecture of the Southport Historic District consists primarily of buildings constructed after 1779 when the British virtually destroyed Fairfield. It is a valuable concentration of Greek Revival and Victorian structures which were for the most part the homes of substantial men whose wealth came from their involvement in commerce, banking, and shipping.
For many years after its founding in 1639, Fairfield was the center of political and commercial activity, and Southport (or Mill River) was simply the western end of Fairfield and had no separate identity. Settlement in the area was slow and in 1779 — 120 years after the first settlers began to take up land in the area — there could not have been very many houses or stores along the harbor or river. It is recorded that in July of 1779, the day after British troops had virtually destroyed Fairfield — burning 85 dwelling houses, 55 barns, 15 stores, 15 shops, and the schoolhouses, county jail and the jailor's house and two churches — the British landed at Mill River and burned "8 houses and outbuildings, destroying furniture and whatever they could lay their hands on." It is not known how many houses and outbuildings were in existence at the time, but since the British were probably as thorough in Mill River as they were in Fairfield and since only one house is known to have escaped the burning, it is a fair assumption that while there were at least 9 houses and outbuildings in existence in 1779. There was also a grist mill on Mill River as early as 1662, and for 50 years thereafter the records of the town contain numerous references to grants of privileges to erect other grist mills and fulling mills. But there was no church in Mill River until 1835, though Episcopal services were held there as early as 1828, and since the establishment of a church was a requisite for a community, it would appear that those who lived at Mill River were primarily farmers, cultivating the land that was acquired from the town, and that the center of commercial activity was in Fairfield.
There was a wharf in Hill River as early as 1769 and at least one "market boat" sailed from there in 1775, but it was not until after 1783 that the possibilities of the harbor were further developed. By 1790 there were 10 vessels registered from Mill River, and by 1803 there were 4 shipyards, from one of which in that year the ship "Juno" of 62 tons, was launched. For the next 40 years the growth of commerce and shipping at Hill River was steady — interrupted only by the Embargo Acts of 1807 and the War of 1812. More shipping was owned in Southport, in proportion to its size, than in any other port between Boston and New York, and by 1836 there were 60 to 70 houses, 8 stores, an academy, an bank and a church.
This turning away from agriculture toward the sea is especially significant for its effect on young men growing up in Southport. Their horizons widened; they learned the elements of trade and commerce at an early age and did not hesitate to leave their birthplace and seek their fortunes elsewhere. But those who remained behind also found opportunities for profitable business ventures. By 1849 Southport with its good harbor and outlook toward the sea had developed commercially beyond Fairfield. The New England Mercantile Directory for that year has 31 entries for "Fairfield" of which 15 are listed for Southport, 11 for Fairfield and 5 for Greenfield Hill.
In 1831 the area between the Harbor and Mill River and Sasco Creek was officially designated as a separate Borough and was named "Southport." The action requesting the General Assembly to grant permission to establish the Borough was the result of the great increase in shipping and commerce, which meant that the local problems in the Mill River community differed from those of Fairfield itself and would therefore lend themselves to better solutions through local autonomy. With the advent of the railroad in 1848-49, the emphasis and reliance on shipment and travel by water lessened very sharply, and the borough status of Southport was abandoned in 1854, though the name has remained.
During this period of about 50 years the prosperity of this community was based on the harbor, and Southport became the residence of men of substantial wealth whose interests were in shipping here and elsewhere. The shipyards and wharves and warehouses and stores and market boats have gone, but the harbor is still the hub of interest in Southport. The ships that crowd the harbor today — schooners, sloops, ketches, power boats — are pleasure craft, but they testify to the attraction of the town. The houses built by owners of ships, captains, and merchants of a former day are often lived in by those who find recreation on the water.
Final Report: Establishment of Historic Districts in Greenfield Hill and Southport, Published by the Fairfield Historic District Commission, 1966.
F.S.M. Crofut, Guide to the History and the Historic Sites of Connecticut, New Haven: Yale University Press, 1937.
‡ Constance Luyster, Connecticut Historical Commission, Southport Historic District, Fairfield, Connecticut. nomination document, 1970, National Park Service, National Register of Historic Places, Washington, D.C.
Center Street • Church Street • Harbor Road • Main Street • Old South Road • Pequot Road • Rose Hill Road • Westway Road • Willow Street