Throwback Thursday – Launching of The Fleet

“Clifford Windsor Sr. first school bus” | Clara and Clifford Windsor Jr. Family Collection | Montauk Library Archives
“Clifford Windsor Sr. first school bus” | Clara and Clifford Windsor Jr. Family Collection | Montauk Library Archives

When school starts this week the yellow buses won’t look so different from the first one Cliff Windsor sent out to transport Montauk students in the 1940s. He must have been proud; these photos come from an archival collection donated to the Montauk Library by his son, Clifford Jr., and his son’s wife, Clara Windsor.

Stationed in Montauk with the Navy during World War I, Cliff Sr. worked as a road foreman for the Montauk Beach Company and at various times ran a gas station and a school bus company as well as a hardware store that he sold to the Pfund family. His wife, Nellie, operated a telephone switchboard from their home. She was said to know more than anyone about the local news, and also served during World War II in the American Women’s Voluntary Service.

Their son, Cliff Windsor Jr., was a veteran of World War II. His wife, the former Clara Bennett, was a descendant of the Round Swamp Lester family from East Hampton. Living on North Shore Road in Montauk, the couple for decades ran the Windsor family’s bus company, with Clara Windsor also working as a bus driver.

What happened after the younger Windsors retired from the bus business in the 1970s?

According to Jack Perna, the Montauk School District superintendent, they sold their company to the Mensch family, who named it Montauk Bus. Ironically, that business moved west and is still operated by the Mensches under the same name. The Mensches sold the Montauk portion of the business to the McCoy family of Bridgehampton, whose buses the Montauk School District bought when the McCoy Bus Company went out of business. The district now rents the former Windsor property on North Shore Road to house its school buses.

“You will see ‘Montauk Bus’ buses in Montauk. They work for BOCES,” Mr. Perna said, referring to the program that offers expanded educational services up the island in places like Westhampton. “You will see ‘Montauk USFD’ buses also. They are ours.”

Which might be something to think about while waiting for a bus with its red stop arm extended. Thank you, Mr. Perna, for the lesson in transportation history– and have an excellent school year!

#Montaukhistory #Montaukschool #Montauklibrary #Throwbackthursday #tbt #vintageschoolbus


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