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Southold Historic District

The Southold Historic District was listed on the National Register of Historic Places in 1997. Portions of the content on this web page were adapted from a copy of the original nomination document. [1] Adaptation copyright © 2010, The Gombach Group.


The Southold Historic District is situated along Main Road, (State Route 25) in the Town of Southold, Suffolk County, New York. The Southold Historic District encompasses approximately 3 1/2 blocks of the western end of the unincorporated hamlet of Southold. The Town of Southold (population 20,000) is located on the North Fork of the eastern end of Long Island, 90 miles east of New York City. The hamlet is centrally located within the Town of Southold, which extends to Orient Point on the east, and Laurel to the west, a distance of 22 miles. The town is bordered on the south by Peconic Bay and Gardiner's Bay; and on the north and east by Long Island Sound and Block Island Sound. Except for a few places on the north shore, the land is very level and free from stone, with soil of loam and sand. Southold Town consists of a series of hamlets and one incorporated village, the Village of Greenport. Most of the hamlets are arranged along Main Road, and their civic and commercial centers lie along this same road, Main Road.

The Town of Southold is one of the earliest established English towns in the State of New York, dating its settlement to 1640. The town was and is primarily agricultural, although the summer resort trade began shortly before the Civil War, and the community continues to provide second residences for seasonal visitors. Main Road, laid out shortly after the town's date of settlement, forms an east-west axis through the hamlet and contains business and institutional uses east and west of the Southold Historic District. The Southold Historic District contains a significant concentration of historic resources identified in Southold as part of a survey of historic resources completed by the Southold Town Community Development Office in 1986.

The Southold Historic District developed historically as the first area settlers divided into in-town homestead lots. By 1656 all of the lots along Main Road (then called the Town Street) were allotted to the original settlers, most of whom relocated from Massachusetts and Connecticut. Other streets soon developed perpendicular to the Town Street, extending to the north and south. This settlement period street plan is still evident. The earliest intact house represented in the Southold Historic District is the John Booth House, moved to Oaklawn Avenue, and thought to date to 1656. It is representative of the one-story, gable roofed "Cape Cod" style house found commonly on the North Fork from the 17th through the 20th centuries, detailed with Georgian, Federal or later Neoclassical Revival details. Several 18th century houses survive, many of them in the "half house" style house, being a 3-bay house with the entrance occupying the left or right hand bay, though they are now alongside houses built in the late 19th and early 20th centuries in the Italianate and Colonial Revival styles. These later buildings date to the times of growing prosperity on the North Fork. After the arrival of the Long Island Rail Road in 1844, both agricultural markets and summer visitors could take advantage of the relatively fast and affordable transportation. These mid- to late-19th century residences are largely two-story frame residences, many with an L-shaped, T-shaped or cross-gable plan. They are minimally detailed in the Italianate, or Colonial Revival or Dutch Colonial Revival styles. Most of the buildings are, or were, sheathed in wood shingles, the traditional exterior building material of Long Island. Many of the houses in the Southold Historic District are complemented by contributing barns and outbuildings. Along with the Federal period Presbyterian Church and Manse, the Southold Historic District includes the Greek/Gothic Revival Universalist Church (1835-1837) with its parsonage, and the Spanish Revival St. Patrick's Catholic Church (1926-1927) with its rectory. Several of the residential buildings have or currently serve other functions: The John Budd House served as an inn, church and bank before reverting to its original domestic use; the Barnabas Horton Booth House now serves as the American Legion Hall; the original Southold Academy is now a printing shop; and some single family dwellings serve as professional office space, a bed and breakfast establishment and a group home. Of the 64 principal properties contained in the Southold Historic District, 56 are classified as contributing and 8 are classified as non-contributing. None of the properties included in the Southold Historic District have been previously listed on the National Register.

The majority of the historic buildings in the Southold Historic District are residential buildings built either with a heavy timber frame or balloon frame construction and range in date from c.1656 to c.1938. The Southold Historic District also includes three prominent religious facilities and educational facilities. The Southold Historic District's character is one of a hamlet, with houses in close proximity to each other, but sited on generous lots. The setback of houses is unusually uniform, considering the range of periods represented, and there are relatively few fences and hedges which divide properties from each other. Mature trees and informal lawns and gardens complement many of the historic properties in the historic district and contribute to the Southold Historic District's historic setting and sense of place. A large number of outbuildings survive in the rear yards of the properties, particularly along Main Road.


Representing a c.1656 through c.1938 period of significance, buildings, objects, sites and landscape elements within the Southold Historic District reflect all major phases in the evolution of the hamlet, including the settlement period (c.1640-1780), the prosperous post-revolutionary period (1780-1845), and the period of rail and other forms of commercial transportation (1845-1920). Architecturally, the Southold Historic District is marked by significant examples of Colonial, Early Republic, Gothic Revival, Italian Villa, Italianate, Queen Anne, Craftsman, and Colonial Revival style architecture. The Southold Historic District is primarily comprised of detached residences set on individual lots along Route 25 (Main Road), the main east-west thoroughfare of the North Fork. The character of the Southold Historic District is one of a residential hamlet, bordered on the east by the downtown commercial district, west by altered historic buildings, and on the north and south by post-World War II development and farmland. The Southold Historic District has relatively few modern intrusions, and retains its historic scale, street pattern, setting and landscape character to a significant extent.

Southold is located on the extreme northeast tip of Long Island, on what is referred to as the North Fork, the North Fluke or the North Branch. This part of Long Island acquired its final form with the last of four glaciers, the Wisconsin glacier, 1,000,000 to 25,000 years ago. Southold Town is bounded on the north by Long Island Sound, on the south by Gardiner's and Peconic Bays, and on the west by the Town of Riverhead, and includes several islands in both the bay and sound. With over 157 miles of shore front along the bays, sound, creeks and inlets, Southold is a town where one is constantly in the presence of water. The land comprising Southold was home to the Corchaug tribe of the Algonkians, whose name for the area was "Yennecock" or "Yennecott," meaning an extended stretch of land. The Corchaugs lived primarily at the Southold hamlets of Mattituck, Cutchogue, Aquebogue and Hashamomuk.

Although no town records exist prior to 1651, in 1638 eastern Long Island was the private preserve of Sir William Alexander, the Earl of Sterling, a Scotch poet and dramatist and a favorite of Charles I of England. Alexander never visited the area, and left its promotion to an agent, James Farret, a fellow Scot, who collected rent as of 1638. The first deed was made on August 15, 1640 with Richard Jackson of Massachusetts. The sheltered bays and creeks, and relatively stone-free soils attracted settlers from New England, and by 1640 there was a community which had organized the first church. Southold was unified with the New Haven Jurisdiction until 1662, when the government of Connecticut was extended over New Haven, including Southold. In 1676 Southold submitted, with the same reluctance of other Long Island settlements to the jurisdiction of Sir Edmund Andros.

Considering the early date of settlement and the settlers' English heritage, Southold is considered an early New England settlement. Suffolk County was settled largely by English Puritans who had relocated from New England. The settlers brought with them their building and farming traditions, resulting in a community which, in political and religious structure, agricultural practice and construction traditions, related most closely to the seacoast villages of New England.

The settlement's center was located in the area now known as Southold hamlet. The town street extended from Jockey Creek on the west to Town Harbor Lane on the east, and included the oblique angle still evident opposite Tucker Lane. The settlement center was placed, according to Whitaker, "where it is in some measure sheltered from the winds of the icy winter by the high bluff on the north of it, and where the breezes of the summer come to it from the more distant seas, without its fogs and also tempered by a succession of salt water bays and streams conveniently accessible from the harbor putting up from the deep, broad and beautiful Peconic Bay. From the head of the harbor they opened a road running nearly north ...extending from Peconic Bay to Long Island Sound. Then, at right angles with this road, they laid out the main street of the village (Main Road), running a few points south of west." (Whitaker, p.80) The Town Street, Main Road, is the backbone of the historic district, maintaining its 17th century layout and relationship to the primary development of the hamlet. Roads perpendicular to Main Road running south gave access to the creeks and harbors important to the early industries of Southold, and those running north led to farmlands, areas for grazing, and east to Orient.

As laid out, the settlement's home lots were approximately 4 acres; 16 rods wide on the street and 40 rods deep. Along with the home lot, each freeholder had rights of commonage of 1-7 acres. The church was organized in 1640, and the meetinghouse and cemetery were soon established on the Main Road, approximately where the current church (1803) and burying ground are located. The home lots maintained their 17th century size and layout until the mid-nineteenth century, when lots were subdivided to provide more in-town building lots.

It is evident from early inventories that the settlers had land, houses, barns, fences, horses, cattle sheep, swine and fowls. Farming and fishing were the main pursuits of the majority of residents. The early trades represented by the population — including carpenters, blacksmiths, weavers and shoemakers — show that the community was largely self-sufficient. The little trade outside the county was conducted by water to the New England coastline, New York City and to the West Indies. By 1660 there were at least fifty home lots with their dwellings in the settlement. These settlers built post medieval houses that resembled the vernacular New England structures of their experience. The earliest buildings have braced heavy timber frames with rectangular plans and one and one-half or two-stories high. Small windows, large internal chimneys, and wood shingle siding would have been common elements, with little interior or exterior ornament. Although these houses did likely once line the Town Street, only a few survive, and of those, all have been altered. The basic seventeenth century form can be seen most clearly in the c.1657 John Booth House (875 Oaklawn Avenue), which is a one and one-half story 5-bay Cape Cod style house. Although altered in the 18th and early 19th centuries and moved in the 20th century, the Booth House does retain integrity of its seventeenth century form and type, and the alterations, including a dentilled and bracketed front cornice and fanlight entrance, are contributing elements. Other examples of the seventeenth century form can be seen on their original sites on the north side on Main Road: the c.1656 Bayles-Tuthill-Cory House (48875 Main Road) and the c.1653 Joseph Horton House (51285 Main Road). The John Budd House (600 Tucker Lane) was once located on Main Road, but moved north on Tucker Lane in 1908. Its mid-seventeenth century construction date is based largely on documentation, as the building's form has been dramatically altered in the ensuing centuries.

A focal point of seventeenth century Southold would have been the meetinghouse and adjoining cemetery, established on the Town Street in the center of the village on the highest ground. The current Old Burying Ground contains both the site of the first (demolished) meetinghouse and the oldest graves (many unmarked), dating to the 1670s. The oldest gravestones are located in the northwest corner of the cemetery, and reflect their New England origin by being carved in slate and brownstone. Although the original cemetery was one acre, additional property (app. 5 acres additional land) was acquired by the church after 1784.

Southold's population continued to grow modestly during the eighteenth century. The surviving buildings of the period show that the construction methods and styles of building did not change dramatically, and the small scale of the houses indicate a subsistence economy. The c.1769 Ichabod Cleveland House (50915 Main Road) may be typical for being an eighteenth century house built on a seventeenth century foundation. The one and one-half story, 3-bay house resembles its nearby seventeenth century ancestors. The central section of the Whitaker House (52875 Main Road) may also date to the eighteenth century, and was built in a saltbox form.

The early nineteenth century in Southold was marked by an economic and cultural recovery following the devastating occupation by the British forces during the period of the Revolutionary War. The rebuilding of the trade and agricultural fields resulted in prosperity shown in the community's primary institution, the First Presbyterian Church, built 1803-1808 (the third or fourth building constructed to serve the church). Its large, gable-roofed form is typical of Long Island's post-revolutionary church architecture. With double rows of 12/12 clear glass windows, fully engaged steeple and pedimented door surround, the church represents the rise of the Federal style on the east end. The attenuated proportions of the original construction survive in the interior as well, despite an 1850 remodeling. But even with the economic recovery and several new religious buildings in other parts of the hamlet, the 1824 Gazetteer of the State of New York remarked of Southold that "the houses are principally old, without paint, and poor." The population was 160 families.

A marked change in the formality of Southold's built environment occurred with the construction of two of eastern Long Island's earliest architect-designed buildings, for which we have documentation, both in the Southold Historic District: The First Universalist Church (1835-37) and the nearby Cleveland-Charnews House (c.1835). Architect/builder William Cochran, a native of Connecticut, came to Southold from New York in 1834. While working on the design and construction of his Southold projects, Cochran also kept a hotel from 1834 to 1841 (the John Budd House). Richard Lathers, who later studied with Alexander J. Davis, may have been in partnership with Cochran from 1834-37. Cochran worked in the late Federal style, likely from builder's handbooks, to create a fully realized composition in the Cleveland-Charnews House. With segmental-arched dormers, corner board pilasters, and an in antis front entrance executed in the Doric order, the house is a higher style than anything else surviving from the previous periods. (Cochran's Hartranft House, similar to the Cleveland-Charnews House was demolished in 1986.) The First Universalist Church, built 1835-1837, was designed by Cochran after the congregation had been using Cochran's own inn for its meetings. It was the only Universalist church constructed on Long Island outside of Brooklyn. The unusual design of the church combines elements of both the late Federal and Gothic Revival styles, including an unusual Palladian window with a center lancet window.

Another important cultural institution, the Southold Academy, was established in 1834. The original building was also designed by Cochran, but after 1863 it was sold to the Roman Catholic Church. The present Academy building (380 Horton Lane) was constructed in 1867; it is now used by a commercial printer, but retains a high level of integrity.

By 1840, most of Southold's shipping and shipbuilding had been concentrated in the nearby village of Greenport, whose harbor could accommodate the larger vessels required for whaling and other maritime trade. In 1848, Greenport was cited as having had a more rapid growth than any other village in the county, and 12 ships were engaged in the whaling business there in 1845. This development of the nearby village may have been a reason for Southold's stagnant growth during the period.

The arrival of the Long Island Rail Road in Southold in 1844 dramatically changed the opportunities for overland transportation for the entire island, and particularly those rural areas such as the North Fork. This first Long Island line extended from Jamaica, Queens to Greenport. Originally conceived as a fast mail route for post from New York City to Boston, the railroad soon afforded opportunities to farmers to increase their agricultural markets, and for summer visitors to gain easier access to vacation sites. The changes in agriculture included a shift from pasture land to cultivation, with Long Island potatoes and vegetables taking precedence over grain. In Southold, the combination of intensive agricultural practices and farm machinery caused an increase in land values, including the value of village lots. In 1848, writers Mather and Brockett described Southold as a "growing settlement;" indeed, between 1845 and 1855, Southold's population had the second highest increase of all of Suffolk County's towns.

Summer tourism was also encouraged by the relative ease of access from Brooklyn and New York City. A large hotel developed on Wells Corner, near the center of the village to house summer visitors (dismantled in 1927), and large houses were constructed or converted to sue as rooming houses.

The Town's increased prosperity is evident in the number of buildings constructed along Main Road in the Italianate style c.1840-1880. Many of these buildings replaced the earlier, settlement period houses, and were constructed on narrower lots than those of the seventeenth and eighteenth centuries. Common elements of the Italianate houses in Southold include shallowly pitched roofs with deep eaves; L-shaped, T-shaped or cross-gable plans; round headed windows in the gables; paired front doors; bay windows; and front and side porches. One house, the B.H. Booth House (Main Road), was constructed in the fully realized Italian Villa style by Barnabas H. Booth. A native of Southold, and a member of one of its founding families, B.H. Booth went to Brooklyn during his youth and became a master of the trade of house carpenter and builder. After working in the city for 25 years, he returned to his native Southold and, in 1861, constructed his own house; later, upon the marriage of his sons, he constructed two more hoses nearby for them. When built, Booth's Italian villa house sat in the midst of landscaped grounds on a property that extended from the Main Road north to the railroad. Since 1945, the house has been occupied by the Griswold-Terry-Glover Post 803 of the American Legion, and the land north of the house has been subdivided and developed. Booth was also involved in the construction of the Southold Academy (1867), and may have been responsible for its design.

The increased population and prosperity brought changes to the civic structure of the community. The Southold Savings Bank was established in 1858 (another use of the John Budd House). With the railroad came the Irish and Germans, who laid the railroad tracks and stayed on in the community. The Irish were followed by the Italians, many of whom worked in the brick making and masonry trades and lived in the hamlets. By 1863 a Roman Catholic church was established to serve the religious and social needs of the new immigrants. In 1871, the Lyceum Association established a library.

In 1874, writer Richard Bayles described Southold Town as "a solid and continuous settlement, from one end of its territory to the other. Nearly the whole surface is occupied by farms, and the settlements joining each other in unbroken lined, are compact enough to be pleasant, and still afford sufficient room for the convenient prosecution of farming operations." Of the hamlet, Bayles noted a "thickly settled agricultural district, abounding in highly cultivated farms, and enterprising, successful farmers." He described the main street of the settlement to be approximately 2 miles in length, and to contain four churches, an academy, a savings bank, a newspaper and printing office, a hotel, five stores, several shops and offices. Of the houses, Bayles writes: "Most of the dwellings are large, plain and substantial in appearance, and give evidence of being occupied by a well-to-do, highly civilized, and peace loving community..."

In 1887 the community honored those residents who had served in the Civil War with a monument, located in the small triangular Budd's Park at the intersection of Main Road and Tucker Lane.

Some late nineteenth century houses in the Southold Historic District exhibit aspects of the Queen Anne Revival, particularly in details such as banded glass paired windows and decorative shingling (51225 Main Road). The Universalist Church parsonage was also constructed in the Queen Anne Revival, with an engaged turret and gambrel roof. The building, as designed, had an elegant front porch which has been since enclosed.

By the end of the nineteenth century immigrants from eastern Europe had taken up much of the farmland on the North Fork. Writer Rachel Brooks traced the heritage of the families of 16 farms between Southold in Peconic: in 1876, there were 16 farms, "most" owned by Universalists; in 1928, 12 of the same farms were owned by Poles. Specialized farming, including crops of potatoes, strawberries, cauliflower, brussels sprouts, peas and beans, resulted in yields that were trucked to the New York market.

The replacement of early buildings along the Main Road continued in the early twentieth century. The most popular new styles were the Craftsman Bungalow style (500 Tucker Lane, 52355 Main Road and 51470 Main Road); the Dutch Colonial (360 Tucker Lane and 53245 Main Road); and the Neoclassical Revival (51155 Main Road and details added to numerous earlier structures). Many of the Neoclassical and Colonial Revival buildings may be the work of George W. Smith and Sons builders. Founded in 1908 by George Smith, a native of Southold, this firm worked extensively on the older buildings of the hamlet, at times radically altering the form of an earlier building while preserving some of its historic elements. For example, at the Cleveland-King House, constructed in the eighteenth century as a one and one-half story, 5-bay house, Smith cut the rafters free, raised the roof a full story, and rotated the first floor ninety degrees before patching the building together and creating a Neoclassical exterior with a dentilled and modillioned cornice, elliptical leaded glass transom and leaded glass sidelights, and a gable roofed front stoop with an elliptical soffit and dentils. This distinctive portico design appears on a number of the houses within the district, and may reflect Smith's extensive work in the community. According to Smith's son, Dan Smith, some of the early work of the firm was done with hand tools and traditional moulding planes to better match the existing early work on their projects.

In 1926-27 St. Patrick's Roman Catholic Church and rectory was constructed at the corner of Main Road and Tucker Lane in the Spanish Revival style. The style of the church may have influenced at least one other house, a Mediterranean Revival style stucco house (220 Tucker Lane); there are other stucco houses of the period outside the district.

In 1923, the first section of the Southold School was constructed on Oaklawn Avenue, replacing earlier and more modest school buildings along Main Road. The brick building was enlarged in 1938, with the final composition being a fully realized Neoclassical Revival brick building with a symmetrical front elevation with a central bay, pedimented entrance bay with Corinthian pilasters and an ogee domed cupola. Although later additions have been built on the west side of the school, and the original windows have been replaced, the main building and front facade retain much of their integrity.

Southold suffered the depression and war period with little growth or new construction. Following the war, construction was revived, although primarily in areas that were previously farmed or undeveloped. Areas north and south of the Southold Historic District were developed in the post-World War II years, largely as seasonal communities of small houses or year-round residential development as Cape Cod style or Ranch houses. Remarkably few of these buildings were built along the Main Road, and relatively few were built along the side streets included in the district (Oaklawn Avenue, Tucker Lane and Horton Lane). The boundaries of the Southold Historic District have been drawn to be inclusive of the representative styles and types of buildings in Southold hamlet which retain a high level of integrity of historic scale, street pattern, setting and landscape character. The inclusion of religious and educational facilities within the Southold Historic District is reflective of the establishment of institutions which relate directly to the cultural and social growth of the community. The result is a cohesive hamlet of residences dating from the seventeenth to twentieth centuries, and religious and educational buildings reflecting the growth of the community in the nineteenth and twentieth centuries.


Bailey, Paul, ed. Long Island: A History of Two Great Counties Nassau and Suffolk. New York: Lewis Historical Publishing Co., Inc., 1949.

Bailey, Paul. Physical Long Island: Its Glacial Origin, Historic Storms, Beaches, Prairies and Archaeology. Amityville, NY: Long Island Forum, 1959.

Bayles, Richard M. Bayles' Long Island. Babylon, NY: Budget Steam Print, 1885.

Bayles, Richard M. Historical and Descriptive Sketches of Suffolk County. Port Jefferson, NY: W.A. Overton Jr. and Co., 1874.

Brooks, Rachel Gleason. The Artistic Achievement of a Rural Community — Southold. Southold, NY: Long Island Traveler Print, 1930.

Case, Albertson. Historical Sketch of Southold Town. Southold, NY: Town of Southold, 1876.

Craven, Rev. Charles E., ed. Whitaker's Southold, Being a Substantial Reproduction of the History of Southold, L.I., Its First Century. Princeton, NJ: Princeton University Press, 1931.

Sander, Sam. "Barnabas H. Booth, A Most Prominent Citizen." The Peconic Bay Shopper (February 7, 1984): 5.

Sander, Sam. "The Griswold-Terry-Glover Post 803: The Birth of Southold's American Legion." The Peconic Bay Shopper (May 7, 1985) 5.

Interview with Dan Smith conducted May 6, 1997 by Alison Cornish.

Southold Town Suffolk Co., LI, NY 1636-1939 The Oldest English Town in the State of New York. Southold, NY: Town of Southold, 1939.

Town of Southold Landmark Preservation Commission. Houses of Southold: The First 350 Years. Southold, NY: Town of Southold, 1990.


Atlas of Long Island, New York. Surveyed under the superintendence of F.W. Beers. New York: Beers, Comstock and Cline. 1873.

Atlas of a Part of Suffolk County, Long Island, New York. Brooklyn: E. Belcher Hyde. 1916.

Atlas of Suffolk County, Long Island. Brooklyn: E. Belcher Hyde. 1902.

Hashamomack between Southold and Greenport. Possession of Joseph Conklin Albertson. August, 1838.

Map of Suffolk Co., L.I. surveyed by J. Chace, Jr. Philadelphia: John Douglass. 1858.

  1. John Auwaerter, New York State Historic Preservation Office and Alison Cornish, Southold Historic District, Suffolk County NY, nomination document, 1997, National Park Service, National Register of Historic Places, Washington, D.C.

Southold Historic District Map

Street Names
Horton Lane • Jasmine Lane • Main Road • Oaklawn Avenue • Traveler Street • Tucker Lane

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