Glenfields (Philipstown, New York)

Manitoga was the estate and modernist home of industrial designer Russel Wright (1904–1976) and his wife Mary Small Einstein Wright. It is located along New York State Route 9D south of Garrison, New York, a short distance north of the Bear Mountain Bridge. Wright named his masterful synthesis of architecture and nature Manitoga after Algonquin words meaning "place of great spirit". Today, the home, studio and surrounding woodland garden, together known as Dragon Rock, uniquely convey Wright's enduring ideas about good design and living in harmony with nature. The property was listed on the National Register of Historic Places in 1996. In 2006 the Department of the Interior designated it a National Historic Landmark, the only one to date in Putnam County. Manitoga is a member of the National Trust's Historic Artists' Homes and Studios program and a 2012 World Monuments Watch Site. It is one of the few modern homes open to the public in New York State.

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.

The Garrison train crash occurred on October 24, 1897, in Garrison, New York, at approximately 5:47 am, when train No. 46 of the New York Central & Hudson River Railroad derailed near King's Dock of the Hudson River division, about one and three-quarters miles south of Garrison. All but one of the 19 fatalities drowned when the embankment gave way, plunging the train into the Hudson River. Witnesses described feeling between one and three "thuds" before three of the five sleeper cars fell into the river. Several witnesses described seeing a "hole" in the trackbed after the accident, however, the cause of this was not determined. Early speculation blamed a large explosion of dynamite as the cause of the train's derailment. Two weeks previously, the same train had almost derailed near the same spot when a two-ton boulder was found on the tracks, with some believing it had been deliberately placed.The final report on the cause of the accident was inconclusive, with investigators concluding that either the train derailed and then destroyed the embankment, or that the embankment gave way leading to the derailment. The commission noted that track walkers, employed to walk along the tracks to inspect them, and the embankment, for damage, were not employed during the summer except in periods of heavy storms. It recommended that the number of track walkers be immediately increased.

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.

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.

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.

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.

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.

Webb Lane House is a historic home located at Highland Falls in Orange County, New York. It was built in 1903 and is a two-story brick and stucco dwelling with a hipped roof and deep overhang supported by massive paired brackets. It features an engaged three story tower and a porch supported by heavy timbers. The home has been converted to apartments.It was listed on the National Register of Historic Places in 1982. house pictured is not the Webb lane house. The house in photo is on Michels rd.

Castle Rock is the estate of former Illinois Central Railroad president William H. Osborn in Garrison, New York, United States. It sits on the hill of the same name, looking down on the Hudson River 620 feet (190 m) below. Visible from West Point across the river and traffic on NY 9D passing through Garrison, it has become one of the most recognizable man-made landmarks of the Hudson Highlands.The Osborn family, including paleontologist Henry Fairfield Osborn and his son, conservationist Henry Fairfield Osborn, Jr, has owned and lived in it since it was built by J. Morgan Slade in 1881 as a summer residence, although the original acreage has been subdivided considerably since then. In 1977 it was listed on the National Register of Historic Places. Most of the remaining land is now open to the public for hiking.

James I. O'Neill High School is a public high school in Highland Falls, New York and a part of the Highland Falls-Fort Montgomery Central School District.

Ladycliff College was a small Catholic college in Highland Falls, New York. Founded in 1933 as a woman's college by the Franciscan Sisters of Peekskill, it remained as such until admitting 7 men in 1974. The 1978 and 1979 graduating classes were the largest in school history with 131 graduates each. The school closed after the 1979–80 school year. The school was located adjacent to the United States Military Academy at West Point. The academy acquired the property, and it is the location of the school's museum. The complete history of Ladycliff College is recounted in Ladycliff Remembered: A Journey through Time, a book by Linda Buzzeo Best.