Dr. Holbrook's Military School

The history of Westchester County, a county in the state of New York, can be traced back to the founding of a settlement between the Hudson River and Long Island Sound in the 17th century. The area now known as Westchester County had seen human occupation since at least the Archaic period, but significant growth in the settlements that are now incorporated into the county did not occur until the Industrial Revolution.

The history of Briarcliff Manor, a village in the county of Westchester, New York, can be traced back to the founding of a settlement between the Hudson and Pocantico Rivers in the 19th century. The area now known as Briarcliff Manor had seen human occupation since at least the Archaic period, but significant growth in the settlements that are now incorporated into the village did not occur until the Industrial Revolution. The village, which was incorporated with one square mile in 1902, has expanded primarily through annexation: of Scarborough in 1906 and from the town of Mount Pleasant in 1927.Early leaders of village government include President William de Nyse Nichols from 1902 to 1905, President Walter W. Law, Jr. from 1905 to 1918, President-Mayor Henry H. Law from 1918 until his death in 1936, and Mayor J. Henry Ingham from 1936 to 1941.

The history of Briarcliff Manor, a village in Westchester County, New York, can be traced back to the founding of a settlement between the Hudson and Pocantico Rivers in the 19th century. The area now known as Briarcliff Manor had seen human occupation since at least the Archaic period, but significant growth in the settlements that are now incorporated into the village did not occur until the Industrial Revolution. The village, which was incorporated with one square mile in 1902, has expanded primarily through annexation: of Scarborough in 1906 and from the town of Mount Pleasant in 1927 to its current area of 6.7 square miles (17 km2). The village has also grown in population; from 331 when established to 7,867 in the 2010 census.

Briarcliff Farms was a farm established in 1890 by Walter William Law in Briarcliff Manor, a village in Westchester County, New York. One of several enterprises established by Law at the turn of the 20th century, the farm was known for its milk, butter, and cream and also produced other dairy products, American Beauty roses, bottled water, and print media. At its height, the farm was one of the largest dairy operations in the Northeastern United States, operating about 8,000 acres (10 sq mi) with over 1,000 Jersey cattle. In 1907, the farm moved to Pine Plains in New York's Dutchess County, and it was purchased by New York banker Oakleigh Thorne in 1918, who developed it into an Aberdeen Angus cattle farm. After Thorne's death in 1948, the farm changed hands several times; in 1968 it became Stockbriar Farm, a beef feeding operation. Stockbriar sold the farmland to its current owners in 1979. The farm combined a practical American business model with the concept of a European country seat or manor, with cows being milked constantly, and with milk promptly chilled and bottled within five minutes, and shipped to stores in New York City each night. The farm was progressive, with sterile conditions, numerous employee benefits, good living conditions for livestock, and regular veterinary inspections to maintain a healthy herd. The farm also made use of tenant farming, established working blacksmith, wheelwright, and harness shops on-site, was located around Walter Law's manor house, and constructed numerous buildings in the Tudor Revival architectural style. Briarcliff Farms was the original location for the School of Practical Agriculture and Horticulture, established by the New York State Committee for the Promotion of Agriculture in conjunction with Walter Law. The school's purpose was to teach students in farming, gardening, poultry-keeping, and other agriculture-related skills. The school moved to a farm near Poughkeepsie in 1903, and the school building was run as a hotel for two years until it became Miss Knox's School. After the building burned down in 1912, Miss Knox's School was relocated several times; since 1954, the Knox School has been located in St. James, New York.

All Saints' Episcopal Church is a historic Episcopal church in Briarcliff Manor, New York. It was added to the National Register of Historic Places in 2002. John David Ogilby, whose summer estate and family home in Ireland were the namesakes of Briarcliff Manor, founded the church in 1854. The church was built on Ogilby's summer estate in Briarcliff Manor.Richard Upjohn designed the church building, which was constructed from 1848 to 1854 and expanded in 1911. The church has several memorial windows, including one by John LaFarge and a rose window by Frederick Wilson of Tiffany Studios.

The Briarcliff Lodge was a luxury resort in the village of Briarcliff Manor, New York. It was a notable example of Tudor Revival architecture, and was one of the largest wooden structures in the United States. It was also the first hotel in Westchester County. Walter William Law had it built on his estate, and the Law family owned it until 1937. When the lodge opened in 1902, it was one of the largest resort hotels in the world. The lodge hosted presidents, royalty, and celebrities, and was the scene of numerous memorable occasions for visitors and local residents who attended weddings, receptions, and dances in the ballroom and dining room. For a long time, the lodge was situated among other businesses of Walter Law, including the Briarcliff Farms and Briarcliff Table Water Company. In 1933, the lodge ended year-round service and housed a "health-diet sanitarium" until the Edgewood Park School for Girls began operation there from 1937 to 1954. From 1936 to 1939, the lodge was run again as a hotel in the summer months while the school was closed. From 1955 to 1994, The King's College used the lodge building and built dormitories and academic buildings. Abandoned and unmaintained after 1994, the Briarcliff Lodge was destroyed between 2003 and 2004.

Ossining High School (OHS) is a comprehensive public high school located in Ossining, New York, United States, along the Hudson River in northern Westchester County, New York. Serving grades 9 through 12, it is the sole high school within the Ossining Union Free School District. The school serves the entirety of the village of Ossining, portions of the Village of Briarcliff Manor, Town of Ossining, and Town of New Castle, as well as a very small southern portion of the Town of Yorktown.Its building is a historical contributing property within the Downtown Ossining Historic District, which was added to the U.S. National Register of Historic Places in 1989.

WOSS (91.1 FM) was a radio station broadcasting a Variety format. Licensed to Ossining, New York, United States. The station was last owned by Union Free School District # 1. It’s license got cancelled on June 2, 2022.

Highland Cottage, also known as Squire House, is located on South Highland Avenue (U.S. Route 9) in Ossining, New York, United States. It was the first concrete house in Westchester County, built in the 1870s in the Gothic Revival architectural style. In 1982 it was listed on the National Register of Historic Places; almost 30 years later, it was added to the nearby Downtown Ossining Historic District as a contributing property.Built by a prominent local man with an interest in new construction techniques, it has seen several different uses over the years. It was a sanitarium in the early 20th century, then a hospital and later a restaurant. For most of that century, the Squire family ran a local business school there. Since then it has returned to residential use.

Ossining is a village in Westchester County, New York, United States. The population at the 2020 United States census was 27,551, an increase from 25,060 at the 2010 census. As a village, it is located in the town of Ossining.

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.

The Richard Austin House is located on Croton Avenue (New York State Route 133) in the village of Ossining, New York, United States. It is a wood frame structure dating to the 1870s. In 1989 it was added to the National Register of Historic Places.At the time the house was built, Ossining was beginning its transition from a country town to a commuter suburb of New York City. The Austin House is one of the few from that period of the community's history to remain completely intact, both outside and in, although two extensions were added in the 20th century. It is currently the home of the Ossining Historical Society, which operates a museum in the building.