On September 16, 1858, just as the morning sun was lighting the sky, John Butterfield, dressed in a long linen duster and a "wide-a-wake" hat, left the St. Louis post office with two bags of mail. He got into a Butterfield spring wagon and drove to the depot. There he boarded the Missouri Pacific Flyer for Tipton. He had one passenger with him--William L. Ormsby, a special correspondent of the New York Herald who was a through passenger on the first westbound trip. It took the wood-burning engine 12 hours to pull the train to Tipton (an average of 13 miles per hour). There John Butterfield Jr. waited in a Concord Stagecoach with four fast horses. It took nine minutes to transfer the two passengers and the two mailbags and the coach whipped away toward Springfield.

John Butterfield Sr. rode only as far as Fort Smith but Mr. Ormsby rode all the way to San Francisco. On his arrival he was asked to comment on his journey, "Had I not just come out over the route, I would be perfectly willing to go back." Then he added more bluntly, "I know what Hell is like. I've just had 24 days of it."

All people were elated that the trip could be made in 25 days. The Overland Mail continued to make two trips a week for two and one half years. Each Monday and Thursday morning Overland Mail coaches would leave Tipton and San Francisco on their transcontinental journey. In spite of its unreasonably long route and the punishment inflicted upon the passengers by the rough roads and uncomfortable weather, Butterfield and Co. prospered. The Butterfield Line provided service that was more dependable and rapid than the ships sailing around Cape Horn. Within a month business had grown so that extra wagons had to be added. At first passengers were afraid of Indian attacks but when these did not occur, the passenger travel picked up. Butterfield also inaugurated a daily stage coach line from Tipton to Springfield.

The last Overland Mail trip was made on March 21, 1861. Attacks by the Indians forced the closing of the Gila Trail. Other trails were now in operation and the railroad lines had been extended so the Butterfield Overland Mail Line suspended operation.

The Butterfield office and stables in Tipton were located in a building where the Stop and Shop grocery building is now located. At that time only a dusty plaza separated this building from the depot.