Winifred O'Grady near the Danube during one of her many visits to Germany.
Winifred O'Grady was one of those beloved teachers students never forget.
In more than three decades as a teacher, 13 of them at the former Girls' Latin School in Boston, Ms. O'Grady shaped countless young lives and encouraged some of her students to follow in her footsteps.
"I can definitely say that because of Ms. O'Grady I became a teacher, myself," said Joanne O'Brien, who teaches at the John F. Ryan School in Tewksbury. "I try to emulate her in my classroom."
Ms. O'Grady, who, after she retired from teaching in 1970, took a job in a bookbinding business for the next 30 years, died Monday at the Winchester Nursing Home, where she had lived since October. She was 101.
Her nephew James M. O'Toole, of Milton, a history professor at Boston College, said: "Aunt Winnie never dwelled much on her age. She just kept on living life to the fullest as long as she could. She ate well, never smoked, and stayed active physically and mentally."
Well into her 80s, she was still taking day trips to New York City to attend the opera, rising at 5:30 a.m. to get the bus.
Ms. O'Grady lived in a small Fenway apartment from 1961 to 1999, happy to be within walking distance of museums and Symphony Hall, before moving to Mount Vernon House, a retirement residence in Winchester.
A tall woman, she never wore pantsuits "or dressed down," her nephew said.
Ms. O'Grady, fluent in German, traveled widely, in groups or alone, all over Europe and to Latin America. She made many trips to Germany, home of her maternal ancestors.
In one of the cards and letters she sent relatives was her account of attending the famed Wagner festival at Bayreuth in the summer of 1938 and seeing Adolf Hitler greet the crowd.
"Though she thought his bodyguards were tall and handsome, the Führer himself was, she later recalled, 'kind of shrimpy,' " O'Toole said.
While in a country preparing to go to war, Ms. O'Grady did not hesitate to express her opinion. In letters to her family she told of "deteriorating conditions," he said, and recounted how she had argued politics with German soldiers and others she met on trains.
In 1941, the Federal Bureau of Investigation, aware of her language skills, called her to Washington to read German newspapers and magazines and extract information that might be useful to the government. She returned to teach in the Worcester public schools.
Ms. O'Grady was the eldest of four children born in Clinton to Daniel and Louise (Caefer) O'Grady. She graduated from Commerce High School in Worcester and from Worcester Normal School.
She began teaching in the elementary grades of Worcester public schools, eventually earning a bachelor of education degree from Clark University and a master's in German from Middlebury College.
In 1957, Ms. O'Grady was recruited to teach at Girls Latin School and for a few years, O'Toole said, she commuted from Worcester on "the morning milk train" before moving to Boston.
She left an indelible impression on the young women she taught in the late '50s and '60s.
"Ms. O'Grady was the most caring and supportive teacher in the school," said Jean McGreehan of Billerica, a member of the class of 1967. "Her passion was to teach teenage girls not only the German language, but about culture and living a full life."
McGreehan, who went on to study German at the University of Massachusetts at Amherst, at the University of Freiburg in Germany, and in graduate school, used the language to work as an immigration inspector and in library science. O'Brien said she connected with Ms. O'Grady as a student in her seventh-grade homeroom at Girls Latin.
"In the ninth grade, we had to choose between German and French for the next three years. I took German for the next four because I loved Ms. O'Grady. She always had a story to tell about her trips to Germany and was always so happy and bubbly. Her eyes would sparkle because she loved what she was doing."
Roberta Zonghi, manager of special projects for the Boston Public Library, said the German she studied in Ms. O'Grady's classes has been an asset in her work with scholarly rare books and manuscripts. "Ms. O'Grady really made learning enjoyable," she said. One word Ms. O'Grady didn't use in any language was "retire."
After leaving teaching at age 62, she got a job at Acme Bookbinding, working first in Boston and then in Charlestown. She continued there for 30 years, working half a day five days a week, said Paul Parisi, owner of the family business.
"At work, she had more energy than the young people. She invigorated them. She did hand-sewing and did collating. We trained her here and she was a quick learner."
Anne Parisi, who ran the firm before her son and who hired Ms. O'Grady, said, "Winnie never missed a day of work, even in the coldest weather. She told me that having a job to go to got her up and running."
Ms. O'Grady last visited Germany in 1990, O'Toole said. "She had been there before the [Berlin] wall was up and when it was up, and she wanted to see when it was down."
Ms. O'Grady leaves a sister, Mildred B. O'Toole of Boston.
A Mass will be said at 10 a.m. today at St. Mary's Church in Winchester.
Burial will be in St. John's Cemetery in Clinton.![]()


