Sing Sing

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 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.

Sparta is a neighborhood of the village of Ossining in Westchester County, New York, United States. Sparta borders the Hudson River, south of most of the village of Ossining. The neighborhood was a hamlet of the town of Ossining, and remains its oldest community. Sparta was founded by Dutch settlers in the 17th century. It has zip codes 10510 and 10562. The elevation is 56 feet. The neighborhood includes the Sparta Historic District, the Jug Tavern, and the Sparta Cemetery. The New Croton Aqueduct, Old Croton Aqueduct, Old Croton Trailway State Park, and Trailways State Park Aqueduct transverse the neighborhood. About a mile south of the village green is the Sparta Mine, a silver and lead mine that was worked prior to the Revolutionary War.1 Rockledge Avenue is one of the oldest existing houses in Sparta, and was built circa 1784 by Josiah Rhodes, a man who operated a mustard mill on Sparta Brook with William Kemeys. The property was alleged to be one of George Washington's headquarters during the Revolutionary War. Frank A. Vanderlip expanded and renovated the house in 1921 and added two new wings. He also bought about 70 nearby homes and business buildings. He tore down dilapidated structures, turned some to face the river, and moved at least one house to a new location.

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.

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.

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.

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.

Ossining is a town located along the Hudson River in Westchester County, New York, United States. The population was 40,061 in the 2020 census. It contains two villages, the Village of Ossining and part of Briarcliff Manor, the rest of which is located in the Town of Mount Pleasant. Ossining is the location of Sing Sing maximum-security prison.

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.

The former Brandreth Pill Factory is a historic industrial complex located on Water Street in Ossining, New York, United States. It consists of several brick buildings from the 19th century, in a variety of contemporary architectural styles. In 1980 it was listed on the National Register of Historic Places.Most of the original buildings succumbed to fire in the 1870s, but the oldest, a Greek Revival building possibly designed by Calvin Pollard in the 1830s, remains. Nearby is a corrugated iron structure that may be the earliest use of that material in Westchester County. The main building itself was one of the first to have Otis elevators installed.Benjamin Brandreth made his family's popular medicine, said to treat blood impurities, at the factory, starting in the 1830s. The factory's construction was the beginning of the industrial development of the Ossining waterfront. It continued to be used for manufacturing until the 1940s. Some of the smaller buildings remain in use today, although the former main building is vacant. The village had been considering a proposal to convert the main factory building to green housing. After a proposal to do so failed to gain approval, due in part to flooding concerns in the wake of Hurricane Sandy in 2012, the owners demolished part of the building in 2015. The village claimed it was illegal as the permit had expired; the owners claimed otherwise.

The Ossining Public Library (OPL) is a public library in serving the village of Ossining, New York. The library serves Ossining's school district, including the town of Ossining and neighboring areas. The library was created in the 1880s at the village's Park School. It was first chartered as the Sing Sing Public Library in 1893. Its first permanent location was a Carnegie library on Croton Avenue, replaced by a modern building in 1968, and again replaced with the current facility in 2007.

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.