Norman Rockwell’s History In Westchester

“Without thinking too much about it in specific terms, I was showing the America I knew and observed to others who might not have noticed,” Norman Rockwell reflected in an often-quoted remark.  That idyllic American postwar portrait developed first during Rockwell’s years in Westchester. 

Throughout his half-century career as a magazine illustrator, Rockwell amassed a prolific body of work. A thin man with deep-set eyes, Rockwell approached life with a pipe and a paintbrush. He wore a thousand-yard stare that seemed fixed simultaneously inward and outward. Over the decades, it was his keen eye that ultimately captured what would become 322 iconic Saturday Evening Post covers, 49 Boy Scouts calendars, and countless museum exhibits.

Rockwell moved to Westchester in 1903 when his family settled into the stately Brown Lodge on Mamaroneck’s Prospect Street. At age 9, Rockwell attended Mamaroneck’s only school, spanning elementary through high school, at what is today the Mamaroneck Town Center. Not the sharpest academic, Rockwell turned to art. His eighth-grade teacher spotted the gift and allowed Rockwell to decorate the school with chalk drawings for the holidays. 

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Odd art jobs became a means of extra cash. Celebrated actress Ethel Barrymore soon hired Rockwell as her assistant. As he carried around easels and paint supplies, Rockwell realized he had found his calling. He dropped out of high school and enrolled in The Art Students League of New York in Manhattan. Formal study under illustrator Thomas Fogarty and George Bridgman, who specialized in figure drawing, broadened his palette.


By 16, Rockwell had designed four commissioned Christmas cards and had become art director for the Boy Scouts of America’s magazine, Boys’ Life. Around the same time, his family had to tighten their belts and moved to a boarding house in New Rochelle. It was the early 1900s, and the Golden Age of Illustration had catapulted the careers of Winslow Homer, Maxfield Parrish, and Ellen Pyle. New Rochelle emerged as a haven for commercial illustrators like Frank Leyendecker and Howard Chandler Christy. Rockwell couldn’t have been happier.

He looked back on summers north of Manhattan through rose-colored glasses. Rockwell enjoyed a Tom Sawyer-like stretch of adventure and discovery, exploring and studying New Rochelle’s daily interactions. An art studio in the Clovelly Building at 360 North Avenue became home and cartoonist Clyde Forsythe a close friend. A seasoned veteran, Forsythe worked at The Saturday Evening Post and helped Rockwell secure a job at the publication Rockwell later called “the greatest show window in America.” At age 22, the protégé nabbed his first cover. 

The Post marked the first stroke of Rockwell’s long career portraying the common man. As director Steven Spielberg once said, “Rockwell painted the American Dream—better than anyone.” The famed artist conjured a Leave It to Beaver world of straight lines, bright colors, and rosy faces. Scenes of doctors’ waiting rooms, baseball games, election days, and busy schoolyards documented the delights and disappointments of everyday life. The paintings embodied President Warren G. Harding’s “return to normalcy,” a nostalgia for an easier and humbler time.

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 For each painting, Rockwell meticulously photographed and staged the scene. He aggressively screened models and acted out the expressions he wanted them to wear. This showmanship belied a deep insecurity about his life and work. Crisp small-town paintings ran against a murky personal life. He didn’t get along with his family, married three times, and suffered from frequent isolation and depression. “I paint life as I would like it to be,” he once said. Despite growing success, he wasn’t convinced his art deserved any critical merit beyond magazine publishing. 

In 1943, though, the illustrator painted arguably his most famous work. The Four Freedoms series portrayed what President Franklin D. Roosevelt considered the four fundamental human rights: freedom of speech, freedom of worship, freedom from want, and freedom from fear. The series originally ran in The Saturday Evening Post, and, subsequently, the U.S. Department of the Treasury took the originals cross-country to sell war bonds. The tour raised more than $130 million. Recently, Freedom from Want graced the walls of the National Museum of American Art in Washington, DC.

Breaking with the Post in 1963, Rockwell moved on to Look to cover deeper issues of the Civil Rights Movement and growing poverty. Nonetheless, many historians feel Rockwell’s legacy remains misunderstood and underappreciated. Prominent art circles long dismissed the mass appeal of the illustrations as shallow and hackneyed. It was a criticism Rockwell would take to the grave in 1978.

Yet, no amount of criticism detracted from Rockwell’s wide acclaim. Mamaroneck High School awarded Rockwell an honorary diploma. He received the Presidential Medal of Freedom, the country’s top civilian honor, in 1977. The Norman Rockwell Museum in Stockbridge, Massachusetts, with the world’s largest Rockwell collection, remains dedicated to his legacy. And, today, the New Rochelle Public Library considers The Land of Enchantment, an original Rockwell painting, to be its most prized possession and a fitting illustration of the artist’s journey from Westchester to the world. 

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