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Outsider's View 2021 - More Histories of South Main Street

Updated: Sep 1, 2022

For the last 12 years we have been hosting an annual architectural tour of Southampton that is both one of our biggest fundraisers and one of our most popular events. If you are ever looking for a great way to contribute to the museum and have a great time, this is certainly it.

Originally called Insider's View, the tours consisted of getting a behind the hedge tour of various historic and interesting homes to see their magnificently curated interiors. But over the last two years we have pivoted to Outsider's View. Rather than exploring interior spaces, our event now centers on exploring some of the wonderful garden areas hidden around the Village on private residences.

This year we take a stroll down South Main Street to view some fantastic and historically important homes. Below you can read up about the various locations featured on the tour as well as some of the other gems found along the way.

Please do not trespass onto anyone's private property. Homes on the tour will be marked with a sign on the day of September 11, 2021 and will be on view only from 1 to 4pm. Guests will only be allowed on to the property if they have a wristband.

Limited quantities of tickets are available at the door

if interested, you can purchase your tickets at

17 Meeting House Lane, Southampton, NY 11968


South Main Street

South Main began as a foot path created over 10,000 years ago by early Paleo-Indians and the later Shinnecock Tribe. They created villages for planting and fishing near the ocean in summer, in what is now the estate section. Then moving north along the trail in winter to live in hunting villages on the Peconic Bay. In 1648 English pioneers created farms along South Main Street which became a wagon road and a major trade route for farmers and tradespeople to the now lost seaport of Feversham on the Great Peconic Bay. By the 1880s farmland was quickly evolving into summer estates for the wealthy merchant class. In 1899 Samuel L. Parrish, an affluent NYC attorney, purchased the Rogers Mansion on Main Street to be a summer home and paid for Southampton’s first paved road in 1901.

First Presbyterian Church of Southampton

2 South Main Street

The church boasts one of the oldest congregations in America, established by Southampton’s original settlers in 1640. The structure, a handsome example of the Carpenter Gothic style, is the third used for worship by the congregation and was built in 1843. The church’s founding pastor, the Reverend Abraham Pierson Sr. was a scholarly and zealous Christian whose orthodoxy did not suit his flock. Finding the independent-minded settlers too difficult to control, he left Southampton after eight years. During that time he had devoted much of his missionary zeal toward the native Shinnecocks and even translated Christian texts into their language. Pierson was replaced by a less rigid pastor and the church has remained a vibrant presence in village life ever since. Standing at this important corner location, it is perhaps the village’s most familiar landmark.

The Parsonage

20 South Main Street

The early 19th-century house at #20, just south of the church, is a residence for the church pastor. It boasts a Greek Revival entrance, which supports an unusual projecting second-story bay with an interesting history. It is one of three such bays that were added by the three Herrick sisters to historic Main Street houses around the turn of the last century. One is at the 1708 House north of the former Town Hall/Saks building, and the other is on the former DAR headquarters further south, opposite the Halsey Homestead. It was said that the sisters could shout greetings to each other from their identical perches, though that’s hard to believe. Another story, recounted to the Southampton Press in 1965, recalls that a house belonging to Amanda and Lewis Hildreth, founder of Hildreth’s department store, once stood between the church and #20. The Hildreths are said to have made a land swap with the church, trading their land next to the church for a parcel on the other side of the street, which the church happened to own. On that lot the then-widowed Amanda built the Queen Anne house, #75, as her new home, while her old home was moved to Meeting House Lane and later razed.

Dr. Hallock House

37 South Main Street

With its steep center gable and distinctive fence, the house built for Dr. David H. Hallock in 1866 stands out on South Main Street. Dr. Hallock came to Southampton after practicing in Moriches for 12 years. Family history records that he was “called” to Southampton, which had no doctor at the time. He was to remain in the village for the next 33 years until his death, when his funeral was said to have been “the largest attended funeral ever known in the history of [the] village, the deceased being one of [its] best known and highly esteemed citizens…” After Dr. Hallock’s death, his son George Horace Hallock built a second family home on the property closer to the lake. That was long known as the Doscher house which was purchased in 2005 jointly by the Town and Village of Southampton and later razed with hopes of expanding Agawam Park onto the property.

Fairfield Porter House

49 South Main Street

Built c. 1830-1840, this handsome Greek-Revival dwelling would have been considered an ideal example of a country house at the time—not too big, not too small. It is referred to historically as the Pierson House since it was long owned by members of the prominent Pierson family (including Philetus Pierson, a whaling captain). But it is better known today as the Fairfield Porter House. Porter, a realist painter, lived in the house with his family until his death in 1975 and the house, its grounds, the neighborhood, family, friends, pets and Porter himself are the subjects of many of his paintings. He painted in an old barn at the back of the property and though Abstract Expressionism was dominant in the art world at the time, his realist paintings were—and are—admired by many—in and beyond that world.

The Edwin Post House

74 South Main Street

Known as the Edwin Post House, this imposing residence was built prior to 1858 for a member of the very important Post family. From the early days of the settlement the family has figured prominently among the established landowning interests in Southampton. Most notably, Edwin Post was the formidable Clerk to the proprietor trustees, a powerful entity whose influence over the distribution of the land can hardly be exaggerated. Maps from 1858, 1873 and 1902 list Edwin Post as owner of the house. A Long Island Rail Road brochure, published in 1877 to boost the early summer resort trade, includes a listing for a boarding house hosted by Edwin Post, and is believed to refer to 74 South Main Street. The Edwin Post House was said to accommodate 50 guests, which would have necessitated significant additions to the original structure. Upholding the family’s commitment to civic leadership, Edwin’s son, William J. Post, assumed the position of Town Clerk in 1888, while a cousin, Albert Post, served as the village’s first mayor after Southampton’s incorporation in 1894. 74 South Main Street, once again an impressive private residence, has acquired a modern bay window and front stoop, but it retains its original front entrance with transom and sidelights.

The Hildreth House

75 South Main Street

This house has been singled out as perhaps the most authentic example of the High Victorian Queen Anne Style to be found in Southampton. Built in 1885 by Amanda Hildreth, widow of Lewis (who, it will be remembered, swapped lots with the church), it remained in the Hildreth family until very recently. Leigh Hildreth Berglund, the last Hildreth family link, took great pride in the house’s history in the years that he and his wife lived there. They undertook to research and reproduce the building’s original paint scheme of contrasting colors—painstaking work that was undone by new owners in 2010 who repainted in shades of white. Controversy ensued but has subsided with time.

The Captain Sayre House

95 South Main Street

Built in 1836, this Greek-revival house was moved during the late 1890s to its present location. Captain Edward Sayre was one of 18 whaling captains residing on Main Street at the time and it was said that one would have been safe addressing any adult male met on a Southampton street as “Captain” during the peak of the whaling era. The house is nearly identical to #85, the former Presbyterian parsonage.

The Rectory

100 South Main Street

St. John’s Episcopal Church Rectory is one of the oldest houses in town. Most histories of the house trace its origins to 1730, though Thomas Topping built his house on the site shortly after purchasing the property in 1657 and some elements of that ancient house may have survived. There were successive owner-residents, including members of the Herrick family from whom it was purchased for the church by the Reverend Samuel Fish. It was remodeled soon after, and among other changes, the old farm kitchen with its fireplace and built-in brick oven was repurposed as a dining room. A cape style home, which was a common architectural choice on Long Island in the 18th century, it has undergone extensive renovations, with additions acquired and sometimes removed, though the addition of a large front dormer remains.

St. John’s Episcopal Church

110 South Main Street

St. John’s Episcopal Church was organized in 1908 and held services in Samuel Parrish’s art museum for several years. In 1911 the church purchased the land on South Main Street from Albert Foster and in 1913 the newly constructed St. John’s Church was officially dedicated. From the 77 families that joined in the beginning, the church has grown and thrived over the years and it is today one of Southampton’s most picturesque landmarks.

Linden Lane

The historic marker erected where Linden Lane meets South Main Street signals the existence of a charming “Bungalow Community” conceived by Leon and Isabelle Ward. The Wards purchased land leading down to Lake Agawam in 1925 for their speculative real estate venture—a small development of modest dwellings offering proximity to the lake and simple summertime living, though the houses were intended for year-round use as well. Today the location and charm of the Wards’ development have made Linden Lane one of the village’s most coveted addresses.

The Old Mackie House

129 South Main Street

The Old Mackie House is one of Southampton’s best preserved and widely admired historic houses. It was built in 1742 by John Mackie and is said to be a replica of his house in Scotland. Clad in shingles instead of stone and with its snug one-and-a-half stories, it was well adapted to its New World location more than 200 years ago. John Mackie and the Mackie family would go on to acquire major real estate holdings in the town.

Thanet House

143 South Main Street

Built in 1913 for the son of Dr. Theodore Gaillard Thomas, who is often credited as the founder of the Southampton summer colony, this imposing brick dwelling was given the name Thanet House. Before building, the younger Thomas (also named Theodore Gaillard but known as T.G.) had rented the Sayre home, which had existed on the property previously. Active in real estate, T.G. commissioned Samuel Edson Gage as his architect. Gage designed it in the Dutch style but about ten years later, T.G. had it remodeled into the Craftsman style. T.G. kept the house for 28 years before selling it to Primrose Whitfield Gaynor. Two prominent Southampton physicians have occupied it in the years since: Dr. William C. T. Gaynor and Dr. Kenneth Wright. The Wright family found the house in disrepair and undertook a long and painstaking restoration returning it to its former grandeur.

Restaurateur’s Retreat

152 South Main Street

Built for D.H. Burnett sometime before 1902, this house has the ample porch and shingled tower that were popular architectural elements around the turn of the last century. (There are two houses side-by-side on Little Plains Road with similar features.) In residence in the 1950s and early ‘60s was Nina Gore Olds, mother of author Gore Vidal, who is said to have written one of his books while staying in the tower. Perhaps the most familiar resident to villagers was Herb McCarthy, famous for insulting guests at his famous Bowden Square restaurant, but they always came back for more.

Captain Barney Green House

172 South Main Street

In 1863 Captain Barney J. Green bought this property from Albert Foster. The 17th-century house then existing on the property did not get much use from Captain Green who went to sea at a very young age. His successful whaling career lasted 30 years during which he sailed on all the world’s oceans and called at every post of note. On his last voyage, he was hurled into the air and badly hurt when a whale attacked his boat. He survived but retired from the sea and in 1872 built this sizable and very fashionable Second Empire-style house in which he and his wife ran a very popular boarding house. By 1885 the Greens had stopped taking boarders. In the years since, the house has had several owners who have made some changes but without destroying its historic integrity. The best known of its subsequent owners was Henry Austin Clark Jr., the antique car enthusiast whose Long Island Automotive Museum on Route 27 was long a major attraction in Southampton.

The De Bost House

220 South Main Street

The house at 220 South Main Street built in 1876 by Leon Depeyre DeBost, has gone down in local history as the first summer residence built in the village, preceding Dr. Thomas’s house on the dunes by a year. DeBost’s grandfather, David Schuyler Bogart, served as minister at the First Presbyterian Church in Southampton from 1796 to 1813 and when Leon was orphaned as a child he was sent to live down the street from his grandfather in Southampton. Years later, the land on which he built this Italianate-style house on land purchased by his wife Louise in 1869, became the family’s summer residence. Seen from the street today, it looks almost unchanged from the day of its construction. The DeBosts summered in the house for 18 years before selling it to John W. Kilbreth, whose daughter Mary—notorious for her anti-suffragist activities—inherited the house after her father’s sudden death from a fall on his way to the Southampton post office.

The Thomas Halsey Homestead

249 South Main Street

Established in 1648 by the pioneering Halsey Family who were farmers and land developers. The current house was built by Thomas Halsey, Jr. in 1680 using timber from the original built by his father in 1650. By 1900 Halsey House had become a sprawling guest house for a campus of five buildings owned by the Peabody family. In 1958 Henry Francis du Pont, founder of Winterthur Museum in Delaware, steered the purchase of the property for the Southampton History Museum and removed guest wings to reveal it’s 1680/1730 core. It is the oldest wood-framed building in NYS and open to the public.

The Foster/DAR House

264 South Main Street

This is another Foster house, one of the village’s oldest houses, which local history traces to 1695. It acquired additions circa 1900: the second-story bay is one of the three added by the Herrick sisters to their historic homes. This one dates to 1902 and was added by Edward H. Foster’s wife, nee Herrick. The house is remembered by many as the headquarters of the local chapter of the Daughters of the Revolution. That organization sold the house in 1996 and it is now in private hands.

Penrhyn Cottage

338 South Main Street

In 1892, the Honorable and Mrs. William B. Hornblower purchased seven acres on the east side of South Main Street from the local Sayre family for $10,500, according to Sally Spanburgh’s book on the cottages of South Main Street. Their plan was to build a summer home which they would call Penrhyn (headland). Educated at Princeton and Columbia, Hornblower began his career as a lawyer specializing in bankruptcy. His rise in the profession was spectacular and in 1893 he was appointed by President Cleveland to the Supreme Court but was not confirmed, apparently for purely political reasons. He seems to have stopped summering in the handsome Shingle Style cottage himself in about 1907, renting it out instead. From 1927 to 1957 Penrhyn was owned by Dr. Eric McDonald and his wife, who commissioned Marian Coffin—highly sought after and a legend as one of America’s first professional female landscape architects—to design the cottage’s gardens. Following the McDonalds death, within a year of each other, their heirs continued to own Penrhyn for the next 17 years. Subsequent owners have included Isabel T. Bradley, who made many improvements to Penrhyn’s interior; Mica Ertegun, a well-known professional interior decorator; and Peggy Hill, a Broadway producer who was active locally in producing cultural events in Southampton. The current owner is making the gardens beautiful once again.


354 South Main Street

Robert Henderson Robertson designed this Queen Anne-style home on land he purchased from a larger plot that Dr. Thomas Masters Markoe bought in 1886. Robertson, a prominent architect who also designed the old Rogers Memorial Library on Jobs Lane, among much else, was Dr. Markoe’s son-in-law. In addition to this house, which he built for his family on the northern half of the property and called Wyndecote, he designed, Sunnymede on the southern half for Dr. Markoe (it has a Gin Lane address). The very distinctive Wyndecote has been described as a creative synthesis of the Shingle, Richardsonian and Swiss chalet styles. Its second-floor arched openings and long ground-floor porch are among its many unique and picturesque features. In 1924, Robert’s son and heir Thomas Markoe Robertson married Cordelia Biddle Duke, formerly Mrs. Angier B. Duke. For many years she was a giant presence in Southampton’s summer society who entertained the Duke and Duchess of Windsor and many other high-profile guests at Wyndecote. At her death her sons Angier and Anthony Duke inherited Wyndecote, which stayed in the Robertson-Duke family until 1998

Gin Lane

“Gin” is an archaic English term designating pastureland held in common. The gin where livestock grazed near the ocean was fenced in with a gate that swung only one way. A cow, once in, could not get out until the man who kept the gate released her. This kept the livestock from straying onto the beach or marauding nearby farms. The actual road was created parallel to the ocean shore between 1873 and 1894. In the years since Dr. T. Gaillard Thomas built the first oceanfront summer home there in 1877, it has become the address of choice in Southampton, a place lined today with the mansions of the seriously rich who have an unobstructed view of the Atlantic and never have to worry about a parking place at the beach.

Fairlea Drive

Alfred Nelson bought eight acres of undeveloped land at the foot of South Main Street in 1874 for less than $2,100, adding two more acres in the following years to create a park-like setting for a compound of six cottages. Five were eventually built and the enclave became known as Fair Lea, a play on the middle name of Alfred’s wife, Emily Fairlie Ogden. The socially prominent Nelson was a prosperous importer and banker whose year-round home was Flushing, Queens, where he was very active in his community. Fair Lea’s cottages were all summer rentals and remained in the possession of Alfred and Emily Nelson until her death in 192 when her children inherited the compound. Four years later it was sold to owners who made it a legal subdivision. The historic cottages, all with addresses on Fairlea Drive, are Ingleside (1882), Clover Top (1883), Wild Rose (1883), Overlook (1889) and Fleur-de-Lys (1893). Alterations of varying degrees have been made over the years, during which some of the cottages’ best known occupants have been Anne Ford, daughter of Henry Ford II, Alfred I. Du Pont and Gloria Vanderbilt (Mrs. Wyatt Cooper) who occupied Fleur-de-Lys for several years.

Wooldon Manor

16 Gin Lane

In 1900, Dr. Peter Wyckoff bought property on Gin Lane on Lake Agawam and had his architects design a 58-room half-timber English Tudor colossus for his family. The Wyckoffs were active in the social life of the summer community and locally philanthropic. In 1928, Dr. Wyckoff sold the house to Mrs. Jesse Woolworth Donahue, daughter of the five-and-ten magnate. Jesse Woolworth Donahue was a social striver whose merchant-class background and wayward husband were social handicaps, which she tried to offset with opulence. She undertook an extensive remodeling of the house and the grounds, sparing no expense and when the property to the south became available the estate expanded to 15 acres with 610 feet of oceanfront. But Jesse’s efforts to crack Southampton society failed. With that failure and other personal setbacks—the fatal effects of drugs on her husband and son—she lost interest in the house, which was sold at auction in 1937. In 1940, Charles Merrill acquired the estate and demolished the main house to reduce taxes. What remains is the elaborate beach house added by the Donahues, which is now an elegant residence.

The Bathing Corporation of Southampton

14 Gin Lane

Founded in 1923, this exclusive private club was the scene for many daytime social affairs besides swimming in the ocean and the salt water pool. Southampton’s privileged set including Gary Cooper, Diana Vreeland, Clark Gable and Ann Ford could often be seen entering “The Beach Club.”

St. Andrew’s Dune Church

12 Gin Lane

The church, located at the foot of Lake Agawam, is one of Southampton’s most picturesque landmarks. The nave, built in 1851 as a lifesaving station, was purchased by Dr. T. Gaillard Thomas when the Coast Guard assumed responsibility for rescues. Dr. Thomas donated the building, which was moved in 1879 to its present site to serve as a church. A local carpenter was hired to create its beautiful rustic interior, which is filled with treasures, not the least of which are its 11 Tiffany windows. The church has come under assault from raging seas on several occasions, including in 1938 when it was nearly destroyed by that year’s terrible hurricane. It was lovingly restored and has twice been moved back from the sea. Though it is non-denominational, its summer services are organized under the direction of St. John’s Episcopal Church.

437 views2 comments


Sep 11, 2021

This is wonderful; it should be part of a book! I love the details --- Reverend Pierson translating text into the Shinnecock language...the explanation re. Gin Lane, oh and so many more!


This was a fantastic read, Connor. Thank you!

Pam Aldridge Damus

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