The visit of the American Fleet in 1908 was a major occasion for New Zealand, and people flocked to the port of Auckland to catch a view of the fleet. Masterton Mayor Phillip Hollings was invited to take part in the celebrations incidental to the visit. Fleet Street, constructed at the time, commemorates that visit.
It is thought that the street may also contain an old burial site. Tradition has it that members of the Donald family are buried under or alongside the street.