Highlands Country Club was founded in 1898 by several prominent New Yorkers who had homes in the Hudson Highlands. They established the Club for the sports, recreation and socializing interests of the community. Founding members came from Peekskill, Garrison, Highlands Falls and Cold Spring and included the families of Moses Beach, Henry Belcher, Hamilton Fish, William H. Haldane, Archibald G. King, Edward Livingston, J.P. Morgan, William H. Osborn, Edwards Pierrepont, Henry de Rham and Samuel Sloan. Founded with a little more than 100 members, the Club continues its tradition as an unpretentious and recreation-oriented gathering place for members of the broader community.

The Club property lies within the Garrison Grist Mill District, which is listed on the National Register of Historic Places. The Dutch barn, now used for storage by the golf course maintenance staff, and small red farmhouse are rare surviving early 18th century buildings that are associated with the pre-Revolutionary agricultural and tenant farm period in the Hudson Highlands. In 1777, the property was part of the Mandeville farm, at which time the main house just north of Lower Station Road served as Revolutionary Headquarters for General Israel Putnam. The property is now protected through ownership by Open Space Institute (OSI) and a conservation easement held by Scenic Hudson.

Origin of the name Garrison

Gerret Gerretson and his wife Anna Hermansse arrived at Staten Island from Waggenin, Holland in 1660. One of their descendants, Henry Garrison, moved to the Hudson Highlands in 1786. Harry, as he was known, married a grand-daughter of Jacob Mandeville. Their only son, John Garrison, was born in 1795 and became a Judge of Putnam County, and for two terms represented the county in the State Legislature. In 1829, he established the ferry to West Point, which eighteen years later gave his name to the east landing, Garrison's Landing. When the Hudson River Railroad was built and a station placed at Garrison's Landing, it came to be known as Garrison Station, and with the addition of the Post Office, simply as Garrison. In 1866, Harry's sons opened "Highland House" in Garrison, one of the best known summer resorts on the Hudson. In the 1870s, they also took over management of the Grand Union Hotel, across from Grand Central Depot in New York City.