Institution

Named after the Sint Sinck Native Americans who inhabited the land until 1685. In 1693, the 52,500 acres were “transferred” from the Sint Sinck by royal charter to Frederick Philipse and became Philipse Manor. The Philipse family, who remained “Loyal” to the British during the American Revolution, had their property seized after war’s end in 1779, and in 1788 Sing Sing became part of the Town of Mount Pleasant. On April 2, 1813, the Village of Sing Sing became its own incorporated village in Westchester County, NY, the first municipality in the county to receive this designation. Eighty-eight years later, in 1901, the Village of Sing Sing changed its name to the Village of Ossining.The Village is known for the Sing Sing Prison (known until 1851 as Mount Pleasant State Prison) that was constructed upon an abandoned marble quarry on the east bank of the Hudson River in1818. The Village of Ossining evolved to include a concentrated downtown area that became a commercial and social hub with many banks, churches, and thriving storefronts.Ossining High School was built c.1929 to accommodate the growing student population in the village. It is a monumental three-and-one-half story stone and brick Collegiate Gothic style building with slate gable roof, and a tower and central cupola designed by James Gamble Rogers. The school includes a modern three-story addition. Ossining High School is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.

Ossining High School is a c.1929 Gothic Style building that anchors the southern end of the Downtown Ossining Historic District. It is a brick, three-and-one-half story building originally designed by James Gamble Rogers. Ossining High School possesses a tower and central cupola as part of its original structure, along with a modern three-story addition. A surviving example of pre-Great Depression architecture, it is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.

Ossining High School (Downtown Ossining Historic District)

Director

The Downtown Ossining Historic District, added to the National Register of Historic Places in 1988, contains the structures that have constituted the civic, religious, and entrepreneurial heart of the Village since the middle of the 19th century. It is located at the confluence of Highland Avenue (known as the Old Albany Post Road in the 19th century), Croton Avenue, and Main Street. Named after the Sint Sinck Native Americans who inhabited the land here until 1685 when it was transferred by Royal Charter to Frederick Philipse. As in the case for much of the western side of Westchester County, the land that comprises downtown Ossining was originally party of Philipse Manor, which consisted of 52,500 acres. The Philipses, a Dutch-American family who owned a vast estate stretching from current day Kingsbridge often Bronx to the Croton River, were loyal to the Crown during the Revolutionary War and faced the seizure of their property by the government of New York State following the war’s conclusion. The estate’s land was subdivided and auctioned off to private owners in the years following the war. Early on, almost all development in Sing Sing Village was concentrated around Hunter’s Landing, a small hamlet surrounding the waterfront area. The establishment of Sing Sing Prison on the Village’s waterfront in 1825 and the growth of a small shipbuilding industry led to an increased need for housing and businesses in close proximity to the waterfront, spurning real estate speculation on the farm properties located between the waterfront and the Old Albany Post Road (Highland Avenue today). Within a few years, most of the properties in this area were sold and then subdivided for the construction of the buildings that would soon comprise downtown Sing Sing Village. As this area grew, the appearance of the buildings on Main Street curving their way downhill from its junction with the Old Albany Post Road and Croton Avenue led to the bestowment of the name “The Crescent" on this part of downtown Sing Sing Village, a name by which it is still known today. Downtown Sing Sing location, slightly uphill from the busy port, caused it to grow as a trade conduit between the farmland of northern Westchester and southern Putnam County and the markets in New York City. Many of the merchant companies who owned the transport vessels that traversed the Hudson River had offices in the downtown area at this time. The extension of the New York Central and Hudson River railroad to Sing Sing in 1851 led to a great deal of additional grown over the latter half of the 19th century as Ossining became increasingly known as a center of industry in the northern Westchester region. It was during this prosperous period, from 1850-1920, that the majority of the structures that comprise the historic fabric of the district were constructed. In October 1972, a fire left twenty families homeless and destroyed twenty-seven downtown businesses, devastating the center of Sing Sing Village’s commercial and civic life. Most of the damaged and destroyed structures were concentrated in an area from 117 Main Street to the intersection of Main, Spring, and Brandreth Streets and also included many of the structures located on Spring Street near its intersection with Main Street. Many of the structures that were destroyed were wood-framed buildings that easily caught fire and burned to the ground before the Ossining Fire Department could save them. The property owners rebuilt many of the destroyed structures utilizing brick masonry construction and did so in the High Victorian Italianate style that was popular at the time. The most prominent example of these was the Barlow Block, built by William and George Barlow to house their hardware and furniture business. Downtown Ossining continued to prosper through the close of the 19th century and the first decades of the 20th, becoming a hub for several local banks in these years, including the Ossining Bank for Savings (1908), Ossining National Bank (1906) and First National Bank and Trust Co. (1930). The Ossining Post building, at 30 South Highland Avenue, was the last of the pre-World War II institutional structures built within the boundaries of the Historic District. The Downtown Ossining Historic District contains a number of historic landmarks including: <ul><li>Barlow Block (129-131 &amp; 133 Main Street)</li><li>Cynthard Building (26 South Highland Avenue)</li><li>First Baptist Church (1 Church Street)</li><li>First National Bank and Trust Company (13 Croton Avenue)</li><li>First Presbyterian Church (34 South Highland Avenue)</li><li>Olive Opera House (63-67 Central Avenue)</li><li>Ossining Bank for Savings (200 Main Street)</li><li>Ossining High School (29 South Highland Avenue)</li><li>Ossining Municipal Building (16 Croton Avenue)</li><li>Ossining National Bank (135-139 Main Street)</li><li>Ossining Post Office (former; 30 South Highland Avenue)</li><li>Trinity Episcopal Church (7 South Highland Avenue)</li></ul>A boundary increase for the Ossining Downtown Historic District was made in 2013 to add four more contributing buildings. These four buildings are:<ul><li>Highland Cottage (included as part of the Boundary Increase; listed on the National Register of Historic Place in 1982; https://theclio.com/entry/123820)</li><li>22-24 Croton Avenue (1928)</li><li>55 Central Avenue, the Fanning Building (1868)</li><li>117 Main Street (c.1880)</li></ul>Special thanks to Joyce Cole, Ossining Village Historian, for her research and contributions to this entry.

The Downtown Ossining Historic District is located at the center of the Village of Ossining in northern Westchester County, NY, in the area that surrounds the intersection of Main Street and Highland Avenue. It includes thirty-seven contributing properties that together represent the civic, religious, and commercial core of the village dating from the late nineteenth and early twentieth centuries. Some of the buildings, especially the four churches, continue to function in their original capacity to this day. Other structures such as the original Bank for Savings, the First National Bank, and a number of the other twenty-five commercial buildings, have new owners and purposes but still exhibit many of their original historical characteristics. In most cases, the exteriors have been well maintained. The architectural styles represented in the district include Victorian Renaissance Revival and Victorian Italianate, as well as Gothic Revival. Also included in the district is a portion of the Croton Aqueduct, which is listed separately on the National Register of Historic Places. The First Baptist Church of Ossining was also listed individually on the National Register of Historic Places in 1973. The Downtown Ossining Historic District was placed on the National Register of Historic Places in 1989. A boundary increase for the Ossining Downtown Historic District was made in 2013 to add four more contributing buildings.

Highland Cottage was erected in 1872 by Henry J. Banker, a wealthy and prominent social figure in the town of Ossining. “Baker had a strong interest in building as evidenced by his novel choice to build the house entirely of concrete. He also initiated the campaign to erect a Methodist church in the town and was a generous benefactor”.[1] In 1881 when Henry J. Banker died, the house was sold to Andrew and Jane Dickey who gave the house the name of “Highland Cottage”[2]. Th house was not in their possession for very long, and in 1887 it was sold to Emma Richards. Shortly thereafter in 1888, it was sold to John Cockcroft who would own the residence until 1905. In 1905, he sold the house to Dr. Amos Squire whose name is now associated with the house.  Dr. Squire was born in Cold Spring, New York. His family immigrated to America in 1632. He received his higher education at the College of Physicians and Surgeons of Columbia University, Class of 1899. Later that year, he opened a private practice in Ossining. Dr. Squire utilized the house to run a private hospital called Grandview Sanitarium, while he and his family lived upstairs. In addition, Dr. Squire was appointed chief physician at Sing Sing Prison. Highland Cottage was transformed into a naval hospital during the first World War between 1917 and 1919. In 1920, it serves as a restaurant called the “Castle Inn” until 1923. The Squire family continued to occupy the top floor.[3]When the restaurant moved out, the Squire family reclaimed the house. In 1925, Dr. Squire became the coroner of Westchester County, a post he held for six years.[4] He continued to pursue his interest in criminology and criminal minds. He gave lectures and presentations on the topic and authored a book called Sing Sing Doctor which was sold globally. Dr. Squire died in 1948, and the house was left to his daughter Evelyn Squire Culp. Evelyn Squire Culp graduated from Columbia University School of Business and then received her L.L.B from St. Lawrence University in Canton New York. She practiced law in New York City and from 1941-52; she also taught finance and law at Briarcliff Junior College.[5] in 1952. She later used the Highland Cottage to privately teach business from her home until 1972. The Highland cottage was a building that architecturally was ahead of its time as one of four concrete nineteenth century structures in Westchester. It is the only one of the nineteenth century structures to retain its original use as a residence.  <h2> </h2>

Highland Cottage—also known as the Squire House after its most prominent owner Dr. Amos O. Squire, was constructed in 1872 on what is now Rt. 9, Broadway. It was the first fully concrete house in Westchester and is one of four existing built in the nineteenth century. The house was added to the National Registry of Historic Places in 1982. Since its construction, the house has served many roles including a sanitarium, a naval hospital, a restaurant, a business school, and then finally a private residence again. 

Highland Cottage 

The First National Bank and Trust Company Building was constructed in 1930s and was the most prominent commercial bank in Ossining at the time. The company’s previous building at the site, constructed circa 1850, was demolished to construct a new bank in the popular Art Deco style. The architectural firm Hoggson Brothers of New York City designed the structure, which is the sole Art Deco structure within the Downtown Ossining Historic District. Following the closure of First National Bank and Trust Company, the building hosted a branch of Barclays Bank of New York for a period of time. After a number of years of vacancy, it was purchased by Emigrant Savings Bank, who now own and operate the building. The First National Bank and Trust Company structure has a stepped design, with a four story, hexagonal-shaped main wing and a one story northern secondary wing. The upper three stories of each of the four facings contains four bays of one over one metal sash casement windows, with carved stone detailing between each window bay, carved gargoyle sculptures at each façade’s corner, and additional ornamentation along the upper frieze. The front façade also contains a raised parapet inscribed with the founding date for the First National Bank and Trust and the behind the façade. The front entryway draws slightly from classical styles with its fluted columns, and is set back from the street by a series of steps on Croton Avenue. The lintel above the doorway was originally inscribed with First National Bank and Trust Company, but is now inscribed with Emigrant Savings Bank to reflect the current owner. The Bank’s exterior walls are made of limestone. The Ossining First National Bank and Trust Company is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.Special thanks to Joyce Cole, Ossining Village Historian, for her research and contributions to this entry.

The First National Bank and Trust Company Building was constructed in 1930s was the most prominent commercial bank in Ossining at that time. It is architecturally significant as the best example of 1930s Art Deco architecture within the Village. It is a pentagonal stone structure situated on a triangular lot at the intersection of Highland and Croton Avenues. The distinctive exterior of the four story building exhibits well maintained elements of the Art Deco and Neoclassical architectural styles. When the Ossining First National Bank and Trust Company ceased operations, the building served as a branch of Barclays Bank of New York. The building in 2023 is home to Emigrants Savings Bank. The Ossining First National Bank and Trust Company is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.

First National Bank & Trust Company (Downtown Ossining Historic District)

The First Presbyterian Congregation was formed in 1763 and originally occupied a site located in what is now Sparta Cemetery on land donated by Frederick Philipse, owner of the vast Philipse Manor that stretched from modern-day Kingsbridge, Bronx to the Croton River. The original building was damaged during the Revolutionary War, prompting the congregation to build a new structure in the village of Sing Sing on the site of the current Trinity Episcopal Church at 7 South Highland Avenue in 1803. As the congregation grew, this church was expanded until it was no longer adequate to house the congregation. The present church was constructed from 1868 to 1870 for a cost of approximately $95,000 by contractor Peter H. Terhune of Binghamton, NY and designed by architect Isaac Gale Perry. Perry was later appointed as the State Architect for the State of New York and designed the final phase of the New York State Capitol in Albany from 1883 to 1899 as well as the New York State Armory in Poughkeepsie in 1891.The church is two stories in height with rectangular massing. The front façade is dominated by two front towers on either side of the main entryway. Typical of the High Victorian Gothic style, the church makes use of the polychrome theme with the contrasting brick colors on window sills, lintels, surrounds, buttress caps, and surrounding the main entrance. The gothic pointed arch motif is used for window openings and entryways. The gabled main entrance, which faces South Highland Avenue, is surrounded with elaborate limestone work. The church originally was constructed with a tall steeple on the southeast tower that was subsequently removed in the 1950s when the building was renovated and modernized. The church is constructed with brick and limestone. The First Presbyterian Church is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.Special thanks to Joyce Cole, Ossining Village Historian, for her research and contributions to this entry.

The First Presbyterian Church is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989. It is architecturally significant as a well-preserved example of High Victorian architecture. This structure is also culturally significant as the home of the First Presbyterian Congregation of Ossining.

First Presbyterian Church (Downtown Ossining Historic District)

Named after the Sint Sinck Native Americans who inhabited the land here until 1685, what is today known as Ossining belonged to the large Manor of Philipsburg from 1693 until 1779. In 1693, the land had been “transferred” from the Sint Sinck by royal charter to Frederick Philipse. The Philipse family, who had remained “Loyal” to the British during the American Revolution, had their property seized after war’s end in 1779, and in 1788 Sing Sing became part of the Town of Mount Pleasant. On April 2, 1813, the Village of Sing Sing became its own incorporated village in Westchester County, NY, the first municipality in the county to receive this designation. Eighty-eight years later, in 1901, the Village of Sing Sing changed its name to the Village of Ossining.Known also as the site of Sing Sing Prison (Mount Pleasant State Prison until 1851) which was constructed upon an abandoned marble quarry on the east bank of the Hudson River. The Village of Ossining evolved to include a concentrated downtown area that became a commercial and social hub with many banks, churches, and thriving storefronts.One of these banks was the Bank for Savings which was founded in Sing Sing in 1854. Designed by New York City architect Lansing C. Holden, the bank’s edifice was constructed in 1908 in the fashionable Beaux Arts architectural style.. The building exhibits small rectangular windows with triangular pediments, radiating voussoirs (wedge-shaped stones used as arches), and bracketed sills—all of stone. Featuring strong geometric forms, Classical details, Ionic columns, and excellent cartouches (oval decorations), to this day it remains one of the most well preserved Beaux-Arts buildings in Westchester County. The Bank for Savings of Ossining is located in the Downtown Ossining Historic District, which was added to the National Register of Historic Places in 1989.

As pointed out by Gray Williams, author of Picturing Our Past: National Register Sites in Westchester County: “At one of the most conspicuous locations in Ossining stands an equally conspicuous building.” He is referring to the Bank for Savings of Ossining, a 1908 Beaux-Arts style building located at the intersection of Highland Avenue and Main Street in the Village of Ossining. Constructed in light gray limestone and possessing two large Ionic columns, the historic structure incorporates symmetrical massing and classical details, including intricately carved reliefs. Once the headquarters of the Bank for Savings of Ossining, the building also served for years as the home of the Ossining National Bank. In 1983, the building closed, and it sat vacant for decades. As of 2023, it is currently experiencing new life as a community building, with financial assistance from the Village of Ossining. The Bank for Savings of Ossining is included in the Downtown Ossining Historic District, which was listed on the National Register of Historic Places in 1989.

Downtown Ossining Historic District

Ossining High School (Downtown Ossining Historic District)

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