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Following the American Revolution, more Americans, and particularly New Englanders, began to recognize the value in educating women, as the new republic "depended on a virtuous and informed citizenry." One woman who was able to take advantage of these opportunities was New Milford's Mary Cornelia Boardman (1819-1891), who attended Sarah Pierce's Female Academy in Litchfield (1798-1833) in 1832 at the age of 13. Sarah Pierce, an educator who started the academy in 1798, believed that women should be taught the same subjects as boys, and enrolled interested students until the 1840s including significant literary voices such as Catherine and Harriet Beecher Stowe.
In 1890, the options for women's education in New Milford began to expand with the opening of the Ingleside School for Girls. Founded by Sarah Sanford Black, Ingleside, Scottish for "fireside", was intended to be a home-like environment that avoided the "scanty and unwholesome dict of too often provided in boarding school," and fostered not only intellectual advancement but also teamwork. The school offered a reduced tuition price at the request of New Milford citizens, with The New Milford Gazette noting it provided "inexpensive opportunities for education at home which otherwise could only be obtained in a distant place at great cost." Courses included arithmetic, geography, history (ancient and modern), English, physics, chemistry, astronomy, art, and "physical training," and a choice of French or German. In an 1890 issue, The New Milford Gazette noted that the school was "no longer an experiment," implying that at the end of the 19th century, opening up a school for just girls would have been considered a gamble.
The school fostered an environment where the girls could have fun with their education, which can be seen in a couple of events in 1892. For example, there was a coffee party where all twenty four ladies present only spoke German. At the closing exercises for the year, Miss Edith Warner was allowed to read her essay entitled "The Woman Who Weeps," which satirized the "fragile weeping heroines" of old romance stories, contrasted with her belief that no woman actually looked attractive while crying.
Though Ingleside closed in 1915, and the property became Canterbury School for Boys, the doorway for women's education centered in New Milford had been opened. This represented a shift away from the early 1800s, where only a few lucky women could receive an education far from home.