Carrie's schoolroom began to garner a reputation in their small Illinois town and was referred to by locals as "The Academy." The reputation was such that each of her seven children was to earn at least two college degrees after studying at home with her.
With such an illustrious reputation, it is easy to see why so many parents were eager to send their own children to Carrie's academy. Many children in town came to study various subjects, especially in preparation for college entrance exams.
Later, many parents paid to have their children attend classes taught by Carrie.
By 1883, Carrie received the names of all the books "prescribed by the University of Wisconsin" for applicants to have read and understood. This prompted more work in the schoolroom and she began assigning weekly essays to each of her children preparing for college. Carrie thought of her eldest children: Paré, May, and Gene (Eugenia) as her "Senior," "Junior," and "Sophomore" in the Academy that year.
The first essay assigned was on Longfellow's poem Evangeline and each student was to "tell the story in prose." Carrie, pleased with the results of the first assignment, planned for more essays. Next, they read and wrote on Shakespeare's play The Merchant of Venice and George Eliot's novel Romola.
The reading of the prescribed books was done on Saturday evenings, with one person reading from the book to those assembled.
In January 1886, two new students joined the Academy. Each hoped to pass the state teacher certification exam in March. May, too, was hoping to take the exam, so the three students studied some of the required subjects as a group: arithmetic, pedagogy, geography, grammar, and history.
Carrie managed to teach these subjects in addition to others that were ongoing. She was also teaching Latin to the three seven- and nine-year-old students (two were her own children). In a letter to Ed, Carrie claimed that in Latin, the "urchins" were doing quite well. She also mentioned there was a correspondence course in mineralogy being offered by the Boston Society of Natural History. In deciding to take the course, Carrie claimed that she would be prepared to "'give Charley and Alice a drill when they are ready for it although May and Gene had no time for it.'"
Carrie's ambitions for her children were not always met, however, as in a letter to Paré she suggested they could read Gibbon's Rome during the summer vacation. "'We could read for two hours every morning and still have time for some essays etc. from you students.'" Gibbon's work never left the reading list.
After May, Paré, and Gene returned to college in Madison in the fall of 1886, Carrie continued classes at the Academy with seven students. These included two of her younger children, Charley and Alice. Two more students would have been added to the roster and several others had been considered, but Carrie decided against admitting them after interviews were completed.
The workload was heavy. Carrie was teaching two classes in Latin to students at different levels in addition to the usual courses.
Carrie still found time in her busy Academy work schedule to advise her children on their educational affairs away from home. May wrote home, dismayed by her slow progress in Greek. Carrie advised:
As to your Greek, don't be discouraged. Gene may have a better verbal memory than you but don't she spend more time on a lesson then you? Be sure you give time enough. Of course it will be harder for you after a year in which you scarecely looked at a Greek book. The only remedy is more time on each lesson now. I wish I could impress this on you as I would like...[T]ake my advice and...see if it does not grow easier.
Always supportive of her children's endeavors, Carrie was willing to continue her own education to further the education of her children and the others in the Academy. Two college degrees for each of her children would not be far off as the Academy's reputation predicted.
Always searching for more ways to expand her children's education, Caroline organized the Winston Literary Society. The first meeting was held in the spring of 1886.
The program included an evening meeting held in the Academy room with contributions made by all students currently under her tutelage. Parents and family members of many of the students listened to readings, recitations, original stories, and a debate.
Exercises vastly improved the students' comprehension and writing skills. Of the work completed, Mary commented, "'This exercise has seemed to do us a great deal of good. Not only in improving our comprehension but also our ability to judge of the authors. I know more about the style of those works we have read and written about than I would if I had read two or three of their books.'"
However, not all reading done by the Winston family was of a studious nature. In a letter to her brother, May claimed she had "'indulged in a little luxury this week'" because she was "'reading a novel. Of course the wickedness of this action cannot be sufficiently estimated. Papa said he believed I was getting lazy and reading novels. I told him I had only a novel. But to come to the point it was John Halifax by Phineas Fletcher, which I read...'"
Other popular readings studied by students came from authors such as Hawthorne, Longfellow, Macaulay, Joseph Addison, Bayard Taylor, and Johnson. According to Mary, although they read Hawthorne more than the others, he was still the most difficult to analyze, while Longfellow was easiest for the Academy students.
Although difficult at times, the analysis completed by Academy students served to increase literary comprehension as well as writing and oratory skills.
Bit by the "German Bug"