Thayer Hotel

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

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.

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 house at 365 Main Street, formerly 116 Main Street in Highland Falls, New York, United States, is an Italian Villa style building dating to the mid-19th century. It may have originally been built as the rectory for the nearby Church of the Holy Innocents. It is considered the most accomplished house in that style in the village. In 1982 it was listed on the National Register of Historic Places along with over 50 other historic properties in the Hudson Highlands.

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.

The Smith Rink was an outdoor ice rink on the campus of the United States Military Academy in West Point, New York. The rink served as the home for the Army ice hockey program for 55 years and was the last outdoor venue used for Division I hockey when the program was downgraded in 1973.

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.

West Point is the oldest continuously occupied military post in the United States. Located on the Hudson River in New York, West Point was identified by General George Washington as the most important strategic position in America during the American Revolution. Until January 1778, West Point was not occupied by the military. On January 27, 1778, Brigadier General Samuel Holden Parsons and his brigade crossed the ice on the Hudson River and climbed to the plain on West Point and from that day to the present, West Point has been occupied by the United States Army. It comprises approximately 16,000 acres (6,500 ha) including the campus of the United States Military Academy, which is commonly called "West Point". West Point is a census-designated place (CDP) located in the town of Highlands in Orange County, located on the western bank of the Hudson River. The population was 6,763 at the 2010 census. It is part of the New York–Newark–Jersey City, NY–NJ–PA Metropolitan Statistical Area as well as the larger New York–Newark, NY–NJ–CT–PA Combined Statistical Area.

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 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.

Christl Arena is a 5,043-seat, multi-purpose arena in West Point, New York. It was built in 1985 as part of the Major Donald W. Holleder Center, which also houses Tate Rink. It is home to the United States Military Academy's Army Black Knights men's and women's basketball teams. It was named after 1st Lieutenant Edward C. Christl Jr. '44, a former basketball captain who was killed in combat in Austria during World War II. (Maj. Holleder, '56, the namesake of the athletic center, was an All-American football and basketball player killed in combat in Vietnam in 1967.) The arena hosted portions of the 1995 and 1999 Patriot League men's basketball tournaments, as well as portions of the 2006 and 2008 Patriot League women's basketball tournament, including the 2006 Patriot League championship game, as Army defeated Holy Cross, clinching the first Division I NCAA Tournament bid in program history.