As of 2020, Ridgefield has had 20 school superintendents. Only four were women, but among those was the very first superintendent: Charlotte Wakeman. After she left in 1921, it was 85 years before Ridgefield hired another woman for the job.

An impressive person who was said to be close to six feet tall, “Biddy” Wakeman was remembered not only as a leader in bringing modern education to Ridgefield, but also as a disciplinarian and one who had a fondness for huge hats.

A native of Copake, N.Y., Charlotte J. Wakeman was born in 1877 and grew up in Danbury. She came to Ridgefield in 1906 to be principal of and a teacher at the Center School on Bailey Avenue.

She soon became one of a number of Ridgefielders — educators, parents and “summer people” — who were leaders in modernizing the schools and moving the curriculum into the 20th Century.

In 1915, her classes moved to the new Benjamin Franklin Grammar School and the old Center School became Alexander Hamilton High School. A year later, the district modernized even further by creating the job of school superintendent to oversee all the teachers and other staff. Wakeman held the position while continuing to serve as a teacher.

Wakeman was known for keeping her classes orderly. Tabby Carboni, who had her as a teacher in 1912 and 1913, recalled that “she gave me the ruler many times!”

After World War I, the town was going through a protracted and sometimes bitter dispute about the modernization of schools. By 1921, Wakeman had had enough fighting and resigned. She took a job teaching English at the high school in Mount Vernon, N.Y., remaining there until her retirement in 1937.

However, she continued to live in a small house on Main Street for some years, commuting to Mount Vernon, and maintained contact with her former staff members over the years. Although she held no academic degrees, Wakeman had studied at Columbia, Yale, Dartmouth, and New York University. She was also a founder of the American Woman’s Association, a once active suffragist organization. She died in 1969, aget 91.

Wakeman was known for her hats. During her career in Ridgefield, she was photographed several times wearing enormous hats — in one picture, the hat appears four times the width of her head, and nearly twice as high.

Mary Creagh recalled her as her school’s principal in 1918. “I remember I thought she was very tall and imposing, like a ship in full sail,” said Creagh. “When I met her years later, she didn’t seem that tall at all.”

Perhaps she had taken off her hat.—Jack Sanders