DeRham Farm

Boscobel is a historic house museum in Garrison, New York, overlooking the Hudson River. The house was built in the early 19th century by States Dyckman. It is considered an significant example of the Federal style of American architecture, augmented by Dyckman's extensive collection of period decorations and furniture. It was originally located in the Westchester County hamlet of Montrose. Restoration efforts in the mid-20th century moved it 15 miles (24 km) upriver to where it currently stands, on New York State Route 9D a mile south of the village of Cold Spring in Putnam County.

Saint Basil Academy is a residential school for at-risk students run by the Greek Orthodox Archdiocese of America in Garrison, New York, United States. It is located at Eagle's Rest, previously the estate of Jacob Ruppert, owner of the New York Yankees in the early 20th century, between NY 9D and the Hudson River. During Ruppert's lifetime many Yankees players, including Babe Ruth, were frequent visitors. After his death, the estate remained vacant until 1944, when Archbishop Athenagoras acquired the property for the church and founded the school. In 1982 it was listed on the National Register of Historic Places (NRHP) in recognition of both Ruppert's historical importance and its well-preserved early Twentieth-century architecture.

Normandy Grange is located along NY 9D north of Garrison, New York, United States. It is a Norman-style house and farm complex built in the early 20th century. It was intended to be the gatehouse for Evans Dick's nearby Dick's Castle estate, which was never completed. He and his family lived there during construction of the castle, and found they liked it. In 1982 it was listed on the National Register of Historic Places as part of the Hudson Highlands Multiple Resource Area.

Woodlawn is a former estate house overlooking the Hudson River in Garrison, New York, United States. It was designed in the mid-19th century by Richard Upjohn, who resided in the area for the last years of his life. Later on it became the Malcolm Gordon School, and it is currently the headquarters of the Hastings Center, a prominent bioethics research institution. In 1982 it was listed on the National Register of Historic Places.

Fair Lawn is a house located off NY 9D just south of Cold Spring, New York, United States. It was designed by the painter Thomas Prichard Rossiter, who moved into it for the last decade of his life. Subsequent owners modified the house slightly. In 1982 it was listed on the National Register of Historic Places.

Plumbush is the former house and farm of Robert Parker Parrott, inventor of the Parrott gun. It is located at the junction of NY 9D and Peekskill Road south of Cold Spring, New York, United States. The house was built for Parrott by local architect George Edward Harney in 1865, when he had taken over as superintendent of the nearby West Point Foundry. The property is listed on the National Register of Historic Places since 1992, due to its association with Parrott and Harney's interpretation of patterns by Andrew Jackson Downing.

West Point Light was a lighthouse at the United States Military Academy in West Point, New York. It was located at Gee's Point and was sometimes referred to as Gee's Point Light. West Point Light would be shown on the NOAA Chart 12343 if it were still active. Today, Light 39 (USCG 1-38005), on a skeleton tower with a fixed green light characteristic, has replaced West Point Light on Gee's Point.

Constitution Island is located on the east side of the Hudson River directly opposite the U.S. Military Academy Reservation and is connected to the east shore by Constitution Marsh. It is the only part of the U.S. Military Academy Reservation on the east side of the Hudson River. Formerly known as "Martelaer's Rock", Constitution Island is the site of the earliest Revolutionary War fortifications in the Hudson Valley. Taken briefly by the British in 1777, the island was re-occupied by American forces in 1778, and made an integral part of Fortress West Point. The island was bequeathed to the military academy in 1909 and has been administered by the West Point Museum ever since. The Education Center was completed in 2016, the Warner House has been completely restored and will be ready as a Museum again in the Spring of 2020.

The Cold Spring Cemetery Gatehouse is located along Peekshill Road in Nelsonville, New York, United States. It is a cut granite Gothic Revival cottage built in 1863, one of the earliest uses of that style in the Hudson Highlands. It is used as a house today and was added to the National Register of Historic Places in 1982. It is a one-story building of coursed granite with a jerkin roof cross-gabled on both north and south (front and back). The roof is pierced by a brick chimney; the arched projecting front entrance is flanked by lancet windows. The east facade, facing the cemetery, has a porch whose roof is supported by four pillars with decorative brackets. There is a projecting bay window on the west side. Both gables are topped by two dormer windows. Opposite the house is a small stone booth with lancet windows, connected to the cemetery's stone wall.The Cold Spring Rural Cemetery Association bought a 30-acre (12 ha) parcel in Nelsonville shortly after its formation in 1862. New York City architects Mead and Woodward were hired to design the grounds while Woodward's frequent collaborator George E. Harney worked on the gatehouse. It was finished by 1865 in time for its photograph to be used in the association's bylaws pamphlet.

The Grove, also known as Loretto Rest, is a historic house located on Grove Court in Cold Spring, New York, United States. It was built as the estate of Frederick Lente, surgeon at the nearby West Point Foundry and later a founder of the American Academy of Medicine, in the mid-19th century. The Italian-villa design, popular at the time, was by the prominent architect Richard Upjohn. In 2008 it was listed on the National Register of Historic Places. A later renovation replaced its original roof with a mansard roof. After the Lente family sold it, it was purchased by the Roman Catholic Church and converted to a convent. That use ended in 1977 and it has remained vacant since then, suffering the effects of neglect and decay. The surrounding land was subdivided and developed, eliminating much of Upjohn's original landscaping. In the late 2000s the mansard roof was replaced with one more like the original. It is now the property of the village of Cold Spring, which has attempted to preserve but done nothing to restore the estate.

Kościuszko's Monument is a pedestal and statue of Polish General Tadeusz Kościuszko at the United States Military Academy at West Point, New York. Kościuszko designed the defenses of the West Point garrison from 1778–1780 during the height of the Revolutionary War, when George Washington considered West Point to be the most important military post in America. The pedestal and shaft of the monument was first proposed in 1825 by John Latrobe, and dedicated in 1828. The statue, designed by D. Borja, was later added in 1913.Kosciuszko, having attended the Royal Knights School in Warsaw and audited classes at the Ecole Militaire, advocated the establishment of an American military school for officers, a subject on which he wrote Jefferson many times.: 88  After Jefferson established the academy, General William Davie requested Kosciuszko write the manual, Manoeuvres of Horse Artillery, which became a textbook at the academy.: 257 

The Indian Brook Road Historic District is located on both sides of that street's intersection with US 9 east of Garrison, New York, United States. Its 30 acres (12 ha) contain 15 buildings, all but two of which are considered contributing properties to its historic character. From the late 18th to mid-20th century, the area was a rural hamlet known first as Warrens and later as Nelson's Corner. Unlike most other such small country settlements, it has survived industrialization and the automobile era with its basic plan, and most of its buildings, relatively intact. In 1993, the area was designated a historic district and added to the National Register of Historic Places.