Downtown Ossining Historic District

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.

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: 

• Barlow Block (129-131 & 133 Main Street)
• Cynthard Building (26 South Highland Avenue)
• First Baptist Church (1 Church Street)
• First National Bank and Trust Company (13 Croton Avenue)
• First Presbyterian Church (34 South Highland Avenue)
• Olive Opera House (63-67 Central Avenue)
• Ossining Bank for Savings (200 Main Street)
• Ossining High School (29 South Highland Avenue)
• Ossining Municipal Building (16 Croton Avenue)
• Ossining National Bank (135-139 Main Street)
• Ossining Post Office (former; 30 South Highland Avenue)
• Trinity Episcopal Church (7 South Highland Avenue)

A boundary increase for the Ossining Downtown Historic District was made in 2013 to add four more contributing buildings. These four buildings are:

• Highland Cottage (included as part of the Boundary Increase; listed on the National Register of Historic Place in 1982; https://theclio.com/entry/123820)
• 22-24 Croton Avenue (1928)
• 55 Central Avenue, the Fanning Building (1868)
• 117 Main Street (c.1880)

Special thanks to Joyce Cole, Ossining Village Historian, for her research and contributions to this entry.

1. “Ossining Downtown Historic District #88001827.” National Register of Historic Places. United States Department of the Interior/National Park Service. Aug 9, 1989. https://catalog.archives.gov/id/75323005.  
2. “Ossining Downtown Historic District (Boundary Increase) #12001133.” National Register of Historic Places. United States Department of the Interior/National Park Service. Jan. 2, 2013. https://catalog.archives.gov/id/75323007.  
3. Williams, Gray. Picturing Our Past: National Register Sites in Westchester County. Westchester County Historical Society. 2003.