Charlotte Wakeman, 

The First Superintendent

As of 2019, Ridgefield has had 19 school superintendents. Only three 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. 

In 1915, Ridgefield’s school system was considerably modernized with the addition of the Benjamin Franklin Grammar School, to which her classes were moved, and the opening of Alexander Hamilton High School at what had been the Center School. A year later, the district modernized even further with the creation of the job of school superintendent to oversee all the teachers and other staff. Wakeman held the position and at the same time continued to serve as a teacher. 

Wakeman was 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. When she arrived here, the town had no high school. After Hamilton High opened, Wakeman then focused efforts on making it better. Even students chipped in: The girls in the home economics class under a Mrs. Myer created a “for a better high school” fund to raise money for the school.  

“I bought three hundred-pound bags of raw peanuts,” Wakeman recalled in 1968 when she was 90 years old. “After school the girls under the supervision of Mrs. Myer shelled those peanuts and salted them. Then they sold them at entertainments in the town hall and took orders for them. When they were finished with that, they gave the money made from sales to the Board of Education ‘for a better high school.’”

The girls also encouraged their mothers “to make cakes for several cake sales. They did many other things and gave the profits to the fund.”

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!” Carboni added, however, “I wasn’t bad — there were others who got it a lot more than I did.”

She was also known for her hats. During her career in Ridgefield, Wakeman 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. They were no doubt a style of the day, but she would don them indoors, too, even for group photographs where everyone else was hatless.

After World War I, the town was going through a protracted and sometimes bitter dispute about the modernization of  schools. Leading the support for a conservative approach was school

board Chairman Richard Osborn, owner of the Ridgefield Supply Company. As chairman, “he tangled repeatedly” with  Wakeman, and with Dr. William H. Allee, “her sponsor and supporter,” The Ridgefield Press later reported. (Dr. Allee, covered in a separate Who Was Who profile, was perhaps the most active worker for better education in Ridgefield early in the 20th Century.)

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. In 1937, Ridgefield teachers and friends honored Wakeman on her Mount Vernon retirement, holding a tea for her at the Book Barn on Wilton Road. The attendees included a who’s who of 20th Century Ridgefield educators: Mary Regan, Mary Moylan, Marie Kilcoyne, Mary and Elizabeth Boland, Ruth Wills, Eleanor Burdick, Josephine and Alice Hearst, Margaret and Agnes Carroll, Catherine O’Hearn, Grace White, Isabel O’Shea, Linda Davies, Francis J. Bassett, Charles D. Crouchley, Levio Zandri, and Clifford Holleran.

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 at the age of 91. 

One of the few Ridgefielders alive by the turn of the 21st Century to remember Biddy Wakeman was Mary Creagh, who 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 Miss Creagh. “When I met her years later, she didn’t seem that tall at all.”

Perhaps she had taken off her hat.

David Weingast: 

Superintendent and Scholar

A few days after he accepted the job of Ridgefield superintendent of schools in 1967, Dr. David Weingast was offered a college presidency. 

“I have often wondered what would have happened if I had accepted that instead,” said Weingast in a 1977 interview. But, he added, running a college was “no bed of roses” then, and “I have no regrets. Ridgefield has been a tough superintendency, but you have to remember that I became superintendent at a time when the academic world was a very tough place to be.” 

Weingast, the second longest-serving of the town’s 20 or so superintendents, had indeed worked through tough times, a decade of turmoil with one crisis seeming to come on the heels of another: school building debates, problems with overcrowding, book burning controversies,  budget battles, a very unhappy teachers’ union, and many lesser issues. 

But, he said, it was also a period of accomplishment: the creation of a modern, balanced program of studies, the introduction of greater emphasis on writing, the expansion of fine arts offerings, the increasing use of community resources, the hiring of capable staff, rewriting the whole curriculum from kindergarten through 12th grade using teams of teachers, and the improved management of money. 

“I think we’ve achieved a good balance between teaching the basics and promoting student creativity,” Weingast said. 

The most scholarly of Ridgefield’s superintendents — he wrote four books — and the only one to settle permanently in town,  David Elliott Weingast was born in 1912 in Newark, N.J., and began teaching elementary school there in 1931 at $1,300 a year. 

He received his master’s from Columbia in 1936 and moved to teaching history at Newark’s prestigious Weequahic High School. He got a Columbia doctorate in 1948, was made department chairman, and in 1961, became assistant superintendent for secondary schools in Newark, responsible for nine high schools and six junior highs. 

Meanwhile, he was writing four books: “Walter Lippmann: A Study in Personal Journalism”

(1949), “Franklin D. Roosevelt: Man of Destiny” (1952), “This Is Communism” (1959), and “We Elect A President” (1962). The last two have appeared in several editions, and the Roosevelt book was once chosen one of The New York Times best books for young people.

Before coming to Ridgefield, he received a Ford Foundation grant for study in Europe, concentrating on political systems and the rising tide of communism in Italy. 

In 1975,  Dr. Weingast spent a month visiting Russia, Switzerland and England as one of 25 school superintendents on a trip sponsored by the American Association of School Administrators. He admired the rigor, though not necessarily the approach, of the Russian schools. 

“The program is academically strong, the spirit competitive,” he wrote  after returning. “Academic offerings in the secondary school are compulsory and there are no electives. The Russians would, I think, be bewildered by our system of electives and of our effort to fit a program to every child.”

He retired here when he reached 65, and became a consultant on education, working out of his Main Street home. Like his wife, Bea, he was an active citizen, participated in Rotary and other organizations,  but seemed content to remain on sidelines of Ridgefield politics. 

Occasionally he wrote letters to The Press on issues that interested him — opposing condominiums on north Main Street, supporting expansion of the library.  In 1981, with characteristic thoughtfulness, he opposed a zoning variance to allow an expansion of hotel uses on West Lane. 

“The people who ask for exceptions to the zoning rules mean Ridgefield no harm,” he wrote. “But each applicant wants what he wants. The sum of their wants is more cars, more blacktop, more congestion, more noise, more dirt, more pollution... Beautiful towns don’t decline overnight; they surrender, one building at a time.”

In retirement he had been researching and writing a new book, “The President’s Choice: The Story of the Presidential Cabinet,” but the book had not been completed when Weingast died in 2007 at the age of 94.

His longtime home on Main Street is now the residence of First Selectman and Mrs. Rudy Marconi.

Over his tenure here, his employer, the school board, had caused Weingast much aggravation — at one point the board even voted to fire him, then changed its mind and gave him a new contract. 

When Weingast retired, he was asked if he might ever run for a seat on the school board. 

He laughed loudly.  

“Never!” he said. “I couldn’t be dragooned or seduced or bought!”