House at 365 Main Street

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.

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.

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.

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.

Highland Falls Station in Highland Falls, New York, is a former West Shore Railroad train station built in the 1880s. It was later used by the New York Central Railroad. Since the mid-20th century it has been used as a residence; the tracks are still used as a CSX freight line. It is, along with the Milton Railroad Station to the north in Ulster County, one of the few remaining original West Shore Railroad passenger stations. Its Shingle Style architecture is the most sophisticated example of that mode in the village. In 1982 it was listed on the National Register of Historic Places as Highland Falls Railroad Depot. It was a station for local passenger trains between Weehawken and Newburgh, and for limited trains between Weehawken and Albany. Sequentially, the station south of Highland Falls on the West Shore Railroad was Fort Montgomery. The next station, north-bound, was West Point station for the West Point Military Academy. These trains were discontinued in 1958.

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.

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 Thayer Hotel is a 151-room "Historic Hotel of America" property located 50 miles north of New York City on the banks of the Hudson River at 674 Thayer Road in West Point, New York on the campus of the United States Military Academy. It is named after Sylvanus Thayer, West Point class of 1808, the "father of the Military Academy." It replaced the West Point Hotel in 1926. The Thayer Hotel has three main markets: tourists visiting West Point, weddings, and corporate conferences. The Thayer Hotel came under new management in October 2009. The 151-room hotel has been completely renovated, re-branded, and is now being marketed to host corporate events and leadership training. Renovations completed at The Thayer Hotel in 2012, have brought about the opening of its new executive suite wing, which includes 23 suite-style rooms.

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.

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.

The Buffalo Soldier Monument by Eddie Dixon was installed at the United States Military Academy in West Point, New York, in 2021.

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.