The hamlet was originally settled by five families given a land grant by the King of England in the 17th century and their surnames, King, Terry, Glover, Latham, Tuthill and Vail, still exist in local families. Later, Orient was used as a base of operations by British commanders such as Benedict Arnold and local Tories during the American Revolution to conduct raids on Yankee-held Connecticut. Among Benedict Arnold's headquarters was a local tavern owned and operated by the Vail family on what is now known as "Village Lane". Many of the hamlet's older structures are included in the Orient Historic District, added to the National Register of Historic Places in 1976.