Milford History Online

In 1984, a Milford Christmas tree salesman named Dale Riley walked up the front steps of a colonial house on Old Wilton Road to ask the elderly lady inside if she might donate the large field on her property to stage hot air balloons. He had never met Bernice Perry before, but he had an inkling of why she might say yes: In the 1920s, the former “fly girl” had been the first woman in New England to hold a pilot’s license.  

A contemporary of Amelia Earhart and the early distance and stunt pilots, Perry was one of the original “99ers,” the group of just under one hundred American female flyers led by Earhart. As a girl, Perry had marveled at the World War I planes flying off to Europe, and by the 1920s, she was hanging out at Grenier Field and taking flying lessons. At age 22, Perry was one of just 57 women in the country to hold a commercial transport license, piling up hundreds of hours in the air. Although she graduated from the New England Conservatory of Music, it was flying that was her real love. Perry managed to convert that passion into a career when her husband, Winthrop Perry — a fellow pilot she met at the airport — invented a wing-mounted camera handy for taking aerial pictures. Soon, the photos were being developed down in their basement and the couple’s photography company was in business. Eventually, she became quite an able news photographer on the ground as well and took thousands of photos of Milford for its newspaper, the Cabinet.

So while Bernice Perry did not know the man who stood on her doorstep in 1984, she was curious about his hot air balloon scheme. After all, Perry was always up for an adventure — whether it was landing planes with nearly empty gas tanks in her youth or going for drives during harrowing blizzards in later years. Soon “Perry Field,” (also known as Bernice's back and side yard) was annually filled with balloons of every type, in what would become the Hot Air for High Hopes Balloon Festival. The charity event drew some 30,000 visitors each year and raised tens of thousands of dollars to grant wishes for youngsters with serious illnesses (Perry would donate hundreds of thousands more upon her death). 

Each year, as her yard filled with people, Bernice would stand on her porch loving all the commotion: Kite-flying, helicopters, skydivers, model rockets, wire walkers — and in her mid-80s, she was still going up in balloons with her old friend Dale. As an original fly girl, she no doubt felt right at home.