Baptist minister Calvin Philleo married Prudence Crandall shortly after her attempt in 1833 to introduce a multiracial school for girls to Canterbury, Conn. After Crandall's plans had been ruined by a combination of legal challenges brought by members of the community and violent mob action, the Philleos abandoned the school and state, settling successively in Providence, R.I., New York State, Illinois, and, finally, Kansas.
Calvin Philleo's son by a previous marriage, Calvin W. Philleo, left college at 19 and went to sea where he experienced "much more of adventure and all sorts of life than is usual." By age 25, he had settled in Suffield, Conn., where he studied law with C. F. Cleveland (Democratic Gov. of Connecticut in 1842-43 and later congressman) and George S. Catlin (another congressman). Philleo became an ardent Free Soil Democrat, though he noted that he loved his "profession and its practice far better than ... politics and partizan strife," and he worked closely with the party during the state elections of 1848 through 1852, at one point acting as a Democratic elector and member of the state Democratic Committee. In November, 1849, Philleo married Elizabeth P. Norton, daughter of Daniel W. Norton of Suffield, Conn. The match was a good one for an aspiring politician and lawyer, as his father-in-law was prominent and active in local affairs. Norton's interests included banking, insurance, and textile mills, and he served the community of Suffield variously as Justice of the Peace and as board Member of the Second School Society.
Philleo's literary career was gaining momentum when he died prematurely at 36. He had already published a well-received novel, Twice Married (N.Y.: Dix & Edwards, 1855), and had had stories accepted at Graham's, Putnam's Monthly, the Atlantic Monthly, and other important literary magazines. His legal practice, too, prospered in the early 1850's, as he specialized in representing the claims of descendants of Revolutionary War veterans under the revised pension acts of 1838 and 1855. Philleo's practice was distinguished by his unusual method of accepting a fee based upon the percentage of the claim recovered, admitting no fee if the application were unsuccessful.
Following Calvin W. Philleo's death in 1858, his widow, Elizabeth, appears to have spent time traveling between the homes of relatives in Ohio, Boston, and Illinois. She may have moved permanently to Dayton, Ohio, during or immediately following the Civil War.