Windsor Family Photographs

Collection Owner:
Cover Image:
Pilot Clifford Windsor Sr., World War I, 1910s
Pilot Clifford Windsor Sr., World War I, 1910s

Collection Facts


Historical Context

Born in Maryland in 1894, Clifford Windsor was stationed in Montauk with the U.S. Navy during World War I. Windsor worked as a road foreman for the Montauk Beach Company. In the 1930s he owned a gas station called Windsor’s Garage on Montauk’s Main Street -- the site of the first fire that the newly formed (1939) Montauk Fire Department responded to. Windsor also owned the Windsor Bus Line, which ran the local school buses, and a hardware store that he sold to the Pfund family in 1958.

He and Nellie Taylor were married in 1920. Operating a switchboard from their home, Nellie was the chief telephone operator in Montauk for 13 years. She was, in addition, a member of the Montauk Community Church and one of the original leaders of the Montauk Girl Scouts. Particularly during World War II, she and her husband were deeply involved in such organizations as the American Legion and its auxiliary and civil defense drills mounted by the American Women’s Voluntary Service.
Clifford and Nellie had three children, Clifford Jr. (1922-1984), Eunice (1926-2020), and Alice (1921-1925). A veteran of World War II, Clifford Jr. married Clara Bennett, a descendant of the Round Swamp Lester family from East Hampton. Living on North Shore Road in Montauk, the couple ran the Windsor family’s bus company for three decades before they retired in 1976. Clara Windsor also worked as a bus and taxi driver and helped her father-in-law at the hardware store. Nellie Windsor died in 1950 and Clifford Windsor Sr. died in 1966.

Scope of Collection

The collection consists of photographs donated by the Windsor family of Montauk. There are several aerial images from the 1920s and ‘30s in the collection -- of Montauk’s former fishing village on Fort Pond Bay, its Surf Club on the ocean, and a very early version of its then sparely developed downtown. Subjects of the black-and-white photographs also include a dirigible and crew during World War I, damage from the 1938 hurricane, the fabled Union News Dock on Fort Pond Bay, giant tuna caught by local sportfishing boats in the 1930s and ‘40s, and such local landmarks as the Montauk Manor, the lighthouse, and the original Montauk Downs clubhouse. Clifford Windsor worked as a road foreman for the Montauk Beach Company, which may account for his photos of the 1920s real estate developer Carl Fisher and Fisher’s mausoleum in Miami Beach. One photograph in the Windsor Family Collection tentatively identifies a handsome young man in a leather jacket standing before a biplane in Montauk as “pilot Cliff Windsor Sr. in WWI.” Additional images record drills of the American Women’s Voluntary Services and to a lesser degree, Cliff Windsor’s garage, the family-operated bus company, and their children.