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The Battle of Pine's Bridge was a minor engagement during the American Revolutionary War in the town of Yorktown, New York, on May 14, 1781. Loyalist forces under the command of James De Lancey surprised an American defensive position guarding the Pine's Bridge crossing of the Croton River held by the Rhode Island Regiment (which had some African-American soldiers) along with detached soldiers of the Massachusetts Continental Line and the New Hampshire Continental Line on the north bank of the Croton River, killing and capturing many of the American soldiers. Colonel Christopher Greene and Major Ebenezer Flagg of the Rhode Island Regiment were killed in the action. Greene and Flagg were buried at the 1st Presbyterian Church in nearby Yorktown where their graves are marked by a large monument. Near the monument, a second stone marker and plaque known as the Monument to the First Rhode Island Regiment honors the memory of some African-American soldiers who died defending their commander.

The Croton River ( KROH-tən) is a river in southern New York with three principal tributaries: the West Branch, Middle Branch, and East Branch. Their waters, all part of the New York City water supply system, join downstream from the Croton Falls Reservoir. Together, their waters and the reservoirs linked to them represent the northern half of the New York City water system's Croton Watershed. Shortly after the confluence of the three Croton River branches the Croton River proper, along with its tributary, the Muscoot River, flows into the Muscoot Reservoir, after which it empties into the New Croton Reservoir, which feeds the New Croton Aqueduct supplying water to New York City. Excess water leaves the spillway at the New Croton Dam and empties into the Hudson River at Croton-on-Hudson, New York at Croton Point, about 30 miles (50 km) north of New York City. The river has a watershed area of 361 square miles (930 km2).

Van Cortlandt Manor is a 17th-century house and property built by the van Cortland family located near the confluence of the Croton and Hudson Rivers in the village of Croton-on-Hudson in Westchester County, New York, United States. The colonial era stone and brick manor house is now a museum and is a National Historic Landmark.

The former Washington School is located on Croton Avenue (New York State Route 133) in the village of Ossining, New York, United States. It was built in 1907 in the Beaux-Arts style, one of two in the village to use it. It was added to the National Register of Historic Places in 1987.It was built as a high school, in response to the village's rapid growth following industrialization in the early 20th century, from a design by Wilson Potter of New York City, an architect who specialized in schools. It includes what were at the time some of the most progressive and advanced features of school buildings. Its early (for a school) use of the Beaux-Arts style and placement on a rise in the land give it a monumental quality despite its relatively small size. It is no longer used as a school, and has been turned over to the village for reuse. For a time it housed a museum established by the local historical society. In 1973 it was closed by the school district as part of desegregation efforts. Since a 2009 renovation it has been home to the House of Refuge Apostolic Faith Church. It remains largely as it was originally built, with few alterations.

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 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.

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 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.

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.

Croton–Harmon station () is a train station in Croton-on-Hudson, New York. It serves the Metro-North Railroad's Hudson Line and all Amtrak lines running along the Empire Corridor. It is the main transfer point between the Hudson Line's local and express service and marks the northern endpoint of third-rail electrification on the route. Nearly all electric trains running on the Hudson Line originate and terminate here, though a handful of peak-direction rush hour trains do so further south at Greystone, Irvington, or Tarrytown. As the line's electrification ends just north of the station, trains traveling to or from points north (primarily the northern terminus, Poughkeepsie) are powered by dual-mode (electric/diesel) GE P32AC-DM locomotives. Metro-North used to host an open house of the maintenance facilities every October. The last Open House was in 2008, with the event suspended indefinitely due to renovations of the Harmon shops.Amtrak passengers can travel between the station and New York Penn Station on all Empire routes except the New York City section of the Lake Shore Limited, which stops here only to discharge passengers southbound and to receive passengers northbound.

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 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.