Jay B. Benton was born on April 10, 1870 in Winchester, Massachusetts. He graduated from St. Johnsbury Academy in Vermont in 1885, and five years later graduated from Dartmouth College. Later in 1890, Benton made his way to Boston where he found a job as a reporter for The Boston Evening Transcript. After four years with The Boston Evening Transcript, Benton accepted a position with The Boston Journal as assistant managing editor. Benton sought his pilot's license in 1909 as his interest in ballooning increased, and was the fourth member of the Aero Club of New England to receive his pilot's license. In 1912, Benton and William van Sleet flew the balloon Springfield from Pittsfield, Massachusetts to Pittston, Maine, a distance of 220 miles. During this excursion, the pair established a new record for the longest balloon flight in New England and received an award for maintaining equilibrium. Benton participated in many adventures and mishaps during the pioneer days of balloon flight, and he faithfully recorded his travels and the balloon travels of others through his position as a reporter. Benton was a member of the the Aero club of New England, the Society of Freemasons, the Press Club, the Newspaper Club, and the Papyrus Club.