The Downtown Ossining Historic District is located at the central crossroads of Ossining, New York, United States, and the village's traditional business district known as the Crescent. Among its many late 19th- and early 20th-century commercial buildings are many of the village's major landmarks—three bank buildings, four churches, its village hall, former post office and high school. It was recognized as a historic district in 1989 and listed on the National Register of Historic Places, as one of the few downtowns in Westchester County with its social and historical development intact.
One of its contributing properties, the First Baptist Church of Ossining, was previously listed on the Register in 1973. The Old Croton Aqueduct, a portion of which passes through the district, was listed on the Register the following year and designated a National Historic Landmark in 1992. Among the architects represented in the district are Robert W. Gibson, Isaac G. Perry and James Gamble Rogers.
Ossining began developing at the crossroads in the late 18th century, and continued to prosper as industry, along with Sing Sing prison and the railroad, developed along the nearby shore of the Hudson River. It soon became Westchester's first incorporated village. The downtown area was fully developed by the mid-19th century, but two events later in the century reshaped it. The aqueduct was built through the area to carry water to New York City, requiring the demolition of some buildings. In the early 1870s several fires destroyed other buildings, thus most that remain date from that period to the early 1930s.
Later in the 20th century the buildings on the south side of Main Street were demolished as part of urban renewal efforts. Some of the oldest buildings on the other side were also lost in another fire. Little has been built to replace them, and the village has only recently begun serious redevelopment efforts although the area has become home to restaurants and home-furnishings stores that cater to the area's Latin American and Portuguese immigrant populations. A comprehensive plan adopted in the early 21st century has led to new zoning for the area meant to encourage mixed-use development. An expansion of the district to include Highland Cottage and some other buildings, also called for in the plan, was granted in 2013.
Geography
The district is a area shaped roughly like an upside down "Y". Its boundaries mostly follow property lines and street curbs. It is built around South Highland Avenue (U.S. Route 9), the main north–south through road, and Main Street, which leads west to the river.
At its northern end is 21–22 Croton Avenue, adjacent to the village municipal building along (New York State Route 133). It includes the bank building at the corner with South Highland and then crosses the street to follow the rear line of all the properties on Main Street, the area traditionally known as the Crescent due to the curve resulting from the area's topography. This takes it to the southwest, crossing the aqueduct trailway. At Brandreth Street it veers westward to take in the properties to 55 Central Avenue and, to their south, 107 Main Street.
Then it returns eastward along Main, crossing the aqueduct again to the north side of Church Street. It turns south to follow the rear lines of the properties along South Highland, two commercial buildings and Trinity Episcopal Church, then returns to South Highland at Maple Place. It follows the east side of the road to Emwilton Place, where it turns east to include Ossining United Methodist Church. Past the church it turns north again to include all the buildings of Ossining High School while excluding its more modern athletic facilities. At the high school property's north boundary it turns west again to the rear lines of properties on South Highland, and follows them back to Village Hall.
The 37 buildings and structures within these boundaries are overwhelmingly commercial structures, usually brick buildings of two or three stories. The rest are institutional, either religious or governmental in use. All but 14 are considered contributing properties.
Within the district the land slopes slightly to the north and west, anticipating steeper drops of almost 100 feet (30 m) to the Sing Sing Kill gorge and Hudson. As a result of its proximity to these bluffs the district has a view across the Hudson. To the east and south are the residential neighborhoods of Ossining; in 2013 the district boundary was expanded to include Highland Cottage, also listed on the Register.
The village's 2009 comprehensive plan called for expanding the historic district boundaries, at least for local purposes. Four small areas were proposed for inclusion: the additional properties on Central Avenue, a westward expansion along Main Street, Highland Cottage and the building to the east of the municipal building on Croton Avenue at the northeast corner of the district. These areas were added to the district by the U.S. National Park Service in 2013.
History
The development of downtown Ossining has several distinct stages. In the early preindustrial period, it was primarily a crossroads. Most of the district's buildings, including the four churches, were built and rebuilt along Main Street in the late 19th century. New construction shifted back to Highland Avenue in the early 20th century and gave the district its important public buildings. Since then the community's focus has been devoted to preserving and redeveloping those buildings.
1680s: Formation of the town Frederick Philipse bought the area which presently constitutes the Town of Ossining from the Sint Sinck Native American tribe in 1685. His Manor extended from Spuyten Duyvil Creek on the border between present day Manhattan and the Bronx to the Croton River. The last Lord of the Manor, Frederick III, a Loyalist in the American Revolutionary War, fled to England afterwards, so the state of New York seized the manor in 1779.
1780s–1840s: Crossroads and port When the vast Philipse family landholdings in today's Westchester and Putnam counties were confiscated by the state of New York they were divided among new owners. Elijah Hunter, a Continental Army officer and later a secret agent during the war, bought the tract just south of Sing Sing Kill. He also started holding prayer meetings at his and other settlers' houses; the group formally became the First Baptist Church in 1790.
The river shoreline became the hub of early development. Produce from farms inland was brought there to be shipped to New York City via what is now Main Street, which connected to the Albany Post Road, now US 9. To open the port to even more farmers, the Croton Turnpike (now NY 133) was built early in the 19th century.
Settlement and development began to concentrate around the crossroads. The Union Hotel, just north of the Croton Turnpike, became the travelers' stop identified with Ossining. The local Presbyterian congregation built its first meetinghouse at the present site of Trinity Episcopal Church in 1803. By 1813 it became Sing Sing, Westchester's first incorporated village. The First Baptist Church built its first building at its current site in 1815. In 1820, a relocation of the Post Road a thousand feet (305 m) to the east benefited the new village at the expense of Sparta, the unincorporated hamlet a mile (1.6 km) to the south, since Sparta was no longer on the road while Sing Sing and the Union Hotel still were. Five years later, the local economy was further bolstered when the state built Sing Sing, one of its first prisons, on the river just to the southwest of the village. Marble quarried by convicts was used to build not only the prison but several other buildings in the area, including Ossining's oldest church, St. Paul's, now Calvary Episcopal Church, downtown outside the historic district, and elsewhere, such as the steps of the state capitol and New York City Hall.
The churches grew with the village. In 1834, the Baptist church was renovated, and the Presbyterians built a new Greek Revival church. Many of the commercial buildings in that style along Main Street west of the crossroads were demolished when the Croton Aqueduct, a masonry tunnel, was built in 1839 to connect Croton Dam with the reservoirs in Central Park. The buildings in that style at 151–155 Main Street, built afterwards further east, survived and were the oldest buildings in the district when it was established, but are no longer extant. Only the clapboard Italianate house at 23 South Highland, one of the few residences in the district and now its oldest building, survives from the pre-Civil War period.
1840s–1870: The railroad comes to Ossining
In the middle of the century, the Hudson River Railroad was built along the shoreline. With the village now within an hour's ride of New York City, its population grew over 50 percent between 1845 and 1855. The railroad's effects on the economy were both beneficial and detrimental. It enhanced the agricultural business through the crossroads, and spurred development of industry at the waterfront such as Benjamin Brandreth's pill factory. Industries that had been a source of Ossining's early growth, such as boatbuilding on the riverside and transportation-related businesses like hotels along Albany Post Road, suffered. In 1850, the First National Bank built its first building at the site occupied by its successor at South Highland and Croton.
Little new construction took place during the 1860s, due to the war and its aftermath. The Second Empire Olive Opera House at 63-67 Central Avenue, built around 1865, remains the district's oldest non-residential property. Croton Avenue saw some development at that time, particularly the rowhouses at 4 and the commercial building at 12. On Main Street the buildings between 157 and 161 also date from this time, but those that remain have been altered enough to no longer be contributing. The building at 121 Main Street, built around 1865, retains enough integrity to contribute. After the war, the village built a monument at South Highland and Croton to the 42 men who had been killed in action with the Union Army.
1870–1910: Industrial prosperity
The postwar years, the period later referred to as the Gilded Age, were prosperous for Ossining. While shipbuilding and river shipping finally faded as an industry when the railroad, now part of the New York Central, was fully established, quarrying continued. The village had become an industrial center, with over a hundred small businesses located downtown or on the waterfront, from Brandreth's pill factory to pickle and sleigh manufacturers.
Near the end of that decade the church congregations decided to expand. The Presbyterians needed a larger building. They sold the old one to the new Trinity Episcopal Church, who had split from nearby St. Paul's over differences of opinion about the war. The lot at the Maple Place intersection was ideal for their new building designed by Isaac Perry, later New York's state architect. The stone-trimmed brick structure has design features common to Perry's other churches, all designed during this period.