Sparta, Ossining

The Jug Tavern, also known as the Davids–Garrison House or the Grapevine Inn, is located at the junction of Revolutionary Road and Rockledge Avenue in Sparta section of Ossining, New York, United States. It is a wood frame building, the oldest elements of which date to the mid-18th century, before the American Revolution, making it possibly the oldest structure in the village. It has, however, been expanded and modified since then, and was almost completely rebuilt in the late 19th century. In 1976 it was listed on the National Register of Historic Places.Originally it was located along the Albany Post Road, the central building in the small hamlet of Sparta, a name still used for the neighborhood later absorbed into the village of Ossining and retaining many other intact historic buildings. Much of the house's history is unclear, including whether it was ever even a tavern. Some local legends hold that Revolutionary War figures such as George Washington and John André visited. The name "Jug Tavern" was not even known to have been used for the property until the mid-20th century. A local organization dedicated to preserving the building currently owns the property.

The Scarborough station is a commuter rail stop on the Metro-North Railroad's Hudson Line, located in the Scarborough area of Briarcliff Manor, New York. Trains leave for New York City every hour on weekdays, and about every 25 minutes during rush hour. It is 28.7 miles (46.2 km) from Grand Central Terminal, and the trip there takes about 50 minutes. Trains of electric multiple units serve the station. The Scarborough station is within walking distance of most houses in the neighborhood. Construction of the Scarborough station dates back to the 1860s, when the first station building stood along the Hudson River Railroad, which was completed in 1851 and served areas from New York City to Rensselaer. It became part of the Metropolitan Transportation Authority's Metro-North Railroad in 1983, when the service was created. The station was included in a revitalization plan in 2007 to help serve its commuters. The 1899 station building has housed the Scarborough post office since 1961.

Beechwood is a Hudson River estate in Scarborough-on-Hudson, in Briarcliff Manor, New York. The estate was most notably the home of Frank A. Vanderlip and his family, and is a contributing property to the Scarborough Historic District. The house and property were owned by the Vanderlip family from 1906 to 1979. The property is now a 37-condominium complex as the result of a development project that began in the 1980s. Contemporarily, Beechwood is known for being a filming location of the 1970 film House of Dark Shadows, and a filming location and the primary setting of Savages, a 1972 Merchant Ivory film. In June 2016, Money Man: Frank Vanderlip and the Birth of the Federal Reserve premiered there. The film documents Vanderlip's life and was filmed at Beechwood.

Sing Sing Correctional Facility, formerly Ossining Correctional Facility, is a maximum-security prison operated by the New York State Department of Corrections and Community Supervision in the village of Ossining, New York. It is about 30 miles (48 km) north of New York City on the east bank of the Hudson River. It holds about 1,700 inmates and housed the execution chamber for the State of New York until the abolition of capital punishment in New York in 2004.The name "Sing Sing" was derived from the Sintsink Native American tribe from whom the land was purchased in 1685, and was formerly the name of the village. In 1970, the prison's name was changed to the Ossining Correctional Facility, but it reverted to its original name in 1985. There are plans to convert the original 1825 cell block into a period museum.The prison property is bisected by the Metro-North Railroad's four-track Hudson Line.

The Scarborough Day School was a private school in Scarborough-on-Hudson, in Briarcliff Manor, New York. Frank and Narcissa Cox Vanderlip established the school in 1913 at their estate, Beechwood. The school, a nonsectarian nonprofit college preparatory day school, taught students at pre-kindergarten to twelfth grade levels and had small class sizes, with total enrollment rarely exceeding 150 students.: 46–7  Since 1980, the buildings and property have been owned by The Clear View School,: 158  which runs a day treatment program for 83 students. The current school still uses the Scarborough School's theater, which was opened in 1917. The school campus is a contributing property to the Scarborough Historic District. The Scarborough Day School was accredited by the Middle States Association of Colleges and Secondary Schools and the Board of Regents of the University of the State of New York. The school also was a member of the Cum Laude Society and the National Association of Independent Schools.: 47  Its seal copies that of Scarborough, North Yorkshire; Scarborough-on-Hudson's namesake.: 51 

Ossining station is a commuter rail stop on the Metro-North Railroad's Hudson Line, located in Ossining, New York. It is one of two express stations on that line south of Croton–Harmon, along with Tarrytown, that serve most trains, excluding peak hour trains to/from Poughkeepsie. Trains leave for New York City every 25 to 30 minutes. It is 30.1 miles (48.4 km) from Grand Central Terminal and travel time to Grand Central is about 48 minutes. Near the station is a ferry dock which is used by the NY Waterway-operated ferry connection to Haverstraw, allowing Rockland County, New York commuters to use the Hudson Line as an alternative to the New Jersey Transit-operated lines across the Hudson River. Just south of the station is a section of track which runs through the middle of Sing Sing Correctional Facility.

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.

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.

Dr. Holbrook's Military School was a military academy and boarding school for boys. The school was located in the town of Ossining and overlooked the Hudson River. After the 1906 annexation of Scarborough by the village of Briarcliff Manor, Holbrook's became part of the village within Ossining.The school was founded in 1864 as Mr. Tracy's School. In 1866, after David A. Holbrook purchased the school, it became known as Dr. Holbrook's Military School. The school ran until 1915, after which it was used in World War I as a field hospital and headquarters to a New York Guard regiment. From 1919 until at least 1927, the school served as the Teachers College Country Club.

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.