The Village of Whitesboro is inside the Town of Whitestown.
The village was first settled circa 1784. The village was incorporated in 1813. The Whitesboro seal displays a notable friendly wrestling match between founder Hugh White and a local Oneida chief.
The older part of the village was bordered by the Erie Canal and the village's Main Street. When the canal was filled in the first half of the 20th century, Oriskany Boulevard was built over the filled-in canal. The streets that connect the two roads form the oldest part of the village.
Ice skating was once popular on the Erie Canal, and once covered with ice, the residents used the Flagg Street Playground in the winter to ice skate. The fire department in the 1950s-1980s would spray water on a large area of the several acre playground, and most of the village would come out and skate. A large portion of the village would participate. In the early 1980s, the skating was stopped for insurance reasons.