James I. O'Neill High School

Cragston Dependencies is a group of historic buildings located at Highlands in Orange County, New York. They were built about 1860 as part of the Cragston estate of J. P. Morgan (1837–1913). They consist of a house, barn, well, carriage house, and stable in the Carpenter Gothic style.It was listed on the National Register of Historic Places in 1982.

Stonihurst is a historic estate located at Highland Falls in Orange County, New York. It was built about 1880 and is a two-story clapboard structure on a brick foundation with Gothic style details. Also on the property is a two-story board and batten barn, gatehouse, and gazebo.It was listed on the National Register of Historic Places in 1982.

Fort Montgomery is a hamlet (and census-designated place) in Orange County, New York, United States. The population was 1,627 at the 2020 census. It is part of the Poughkeepsie–Newburgh–Middletown, NY Metropolitan Statistical Area as well as the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area. Fort Montgomery is in the southeastern corner of the town of Highlands, on U.S. Route 9W.

Pine Terrace is a historic home located at Highland Falls in Orange County, New York. It was built about 1865 and is a two-story brick building with a central three story pavilion. It features a slate mansard roof with a wooden bracketed cornice in the Second Empire style. The wooden porte-cochère has trefoils characteristic of Gothic Revival.

St. Mark's Baptist Church, formerly known as Methodist Episcopal Church of Highland Falls, is a historic Baptist church located in the village of Highland Falls, Orange County, New York. It was completed in 1900 and is a modestly scaled, one-story frame building on a limestone ashlar foundation. It features a corner steeple with buttressed corners, open belfry, and windows in the Gothic Revival style.It was listed on the National Register of Historic Places in 2004.

Highland Falls, formerly named Buttermilk Falls, is a village in Orange County, New York, United States. The population was 3,684 at the 2020 census. The village was founded in 1906. It is part of the Poughkeepsie–Newburgh–Middletown, NY Metropolitan Statistical Area as well as the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area. Highland Falls is in the Town of Highlands and is adjacent to the United States Military Academy at West Point.

The house at 20 Center Street, formerly 37 Center Street, in Highland Falls, New York, United States is a frame house built in the mid-19th century in the Greek Revival architectural style. It is one of the few Greek Revival houses, and the highest in style, in the Hudson Highlands. In 1982 it was listed on the National Register of Historic Places.

Manitou station is a limited-service stop on the Metro-North Railroad's Hudson Line. It serves the hamlet of Manitou in the southwestern corner of Philipstown in Putnam County, New York. The station is open part-time, serving one weekday peak hour train in each direction and six weekend trains each direction. The Manitou station is one of three stations – along with Breakneck Ridge on the Hudson Line and Appalachian Trail on the Harlem Line – that receives limited passenger service. Like these stations, it serves mainly hikers visiting nearby state parks in the Hudson Highlands. There is no elevated platform and facilities at the station, one of two on the line adjacent to a grade crossing, are limited to a small shelter with the current schedule posted inside. The station predates the merger of New York Central and Pennsylvania Railroads.This station is the least used station on the Hudson Line, with only 42 passengers per week in 2018.

The Squirrels is a historic estate located at Highland Falls in Orange County, New York. It was built about 1845 and is a two-story frame and clapboard structure with a multi-gabled roof. A two-story frame wing was added to the original farmhouse in 1857 and the house redesigned by architect Calvert Vaux. Also on the property is a one-story gatehouse with a mansard roof. The estate was owned and the house expanded by John Bigelow (1817–1911).It was listed on the National Register of Historic Places in 1982.

The Highland Falls Village Hall is located on Main Street in Highland Falls, New York, United States. It is a three-story Italianate-style brick buildings erected about 1894. Originally it housed a bank for many years. It became the village hall in 1967. It was listed on the National Register of Historic Places in 1982.

Parry House is a historic home located at Highland Falls in Orange County, New York. It was built about 1860 and is a two-story frame dwelling on a brick foundation. It features a slate mansard roof with concave or bell cast sides in the Second Empire style.It was listed on the National Register of Historic Places in 1982.

Glenfields, the former Archibald Gracie King House, is located on Old Manitou Road, a short distance from NY 9D, south of Garrison in the Town of Philipstown, New York, United States. It is a simple late 19th-century frame house with some unusual windows. King was a descendant of Rufus King and other early New York power brokers who had married a descendant of the area's pre-Revolutionary landowners. He built the house, from a design by a local architectural firm, as a summer residence overlooking the nearby Hudson River. In 1982 it was listed on the National Register of Historic Places as part of the Hudson Highlands Multiple Resource Area.