At the 1919 "Welcome Home" Jubilee, Milford was treated to an unbelievable sight — the flight of a gravity-defying airplane. But while seeing a plane was one thing, six years later, residents who were willing to part with a nickel could actually go up in one.
It was on Wednesday November 4, 1925 that local boy Roy Keeley and Taunton's Chet Emerson flew their Curtiss biplane in from Salem, landing in a South Milford field just 14 minutes later. They hoped to spend a few weeks in Keeley’s hometown before a planned trip to the Canadian border. The plane did a few loops overhead and was soon taking up passengers, including five-year-old “Bud” Rossiter who rode with his grandpa while "clapping his hands with glee” as they perused the town from above.
Ten days later, Keeley and Emerson were “doing a general livery, taxi, vaudeville and merry-go-round business” in the air over Fitch’s Field, according to the Milford Cabinet. On the 14th, hundreds of people gathered near Chester Fitch’s house and put their name down on a waitlist to pay the five cents for a quick spin over the Oval.
At the end of the day, the boys put on a short airshow. In those early days of death-defying airplane stunts, this was all but expected. One of the fellows teetered out on a wing while the plane flew close enough to the ground that spectators could make out what was happening in the gathering dusk. On an ominous note, the Cabinet reported that “no high-test airplane gas” was available in town and that the No-Nox fuel poured into the tank reduced the speed of the propeller by a good margin.
Sure enough, the Cabinet was back the following week to announce that Keeley had crashed into a tree in Bristol when his engine went dead. Poor gasoline was to blame. Along with his passenger, the pilot crawled out onto a tree branch where both were rescued with ladders — neither man the worse for wear.
Apparently, just another day at the office for a 1920s pilot.