Milford History Online

In the 1920s, it seemed that there were wing walkers, pole sitters, and human flies everywhere. One such Jazz Age showoff was George Polley, climber of the Custom House Tower in Boston and the Woolworth Building in Manhattan — or at least 30 floors of it before the police said no higher. With such skyscrapers on his resume, Milford’s town hall was no doubt a cakewalk for the daring Mr. Polley. Braving a February 1923 sleet storm, Polley hoisted himself up the building, climbed one of the chimneys and stood on his head waving his legs to the crowd gathered in the Oval below. The Milford Cabinet reported the temperature as zero. Two days later, he climbed the face of the Strand Theater on Middle Street and balanced on a chair. Apparently, the fly was not too pleased with his small-town audience. He took home just $43, “the smallest he ever made.” 

Still, it was enough to make an impression on a fellow called “Daredevil Roland” who stopped through town a couple years later. After assembling his own crowd, he climbed onto the town hall roof and claimed that he would “do all that Polley had done and more.”  However, because it was raining, he lamented that he would need to postpone the feat until the following night. According to the Cabinet, a large crowd was on hand the next evening but “Roland, the human fly, had flew. He had forgotten to bestow the money collected. Milford was annoyed, buzzed at, and stung.”