Personal letters to Milo Kendall, with a short section of outgoing letters, and other family correspondence. Kendall wrote many letters to family and friends in Vermont in the early years of his move to Illinois, and this correspondence documents his efforts to begin a law practice, and also his thoughts on settling in Princeton, getting older, and getting married. Also included are courtship letters to his future wife, Orpha Ide Kendall.

Family correspondence includes letters from Kendall siblings to their parents and each other, as well as members of Orpha Ide Kendall's family. Also included are Orpha Ide Kendall's courtship letters to Milo Kendall, and incoming correspondence to her from her sisters, parents, and friends. There is also voluminous correspondence from Milo & Orpha Kendall's daughter Helen (Nell) Kendall Winter, who lived with her husband and son in the Hyde Park area of Chicago and later Grand Rapids, Michigan. Nell wrote frequently to her parents, and the letters contain many observations of life in Hyde Park, including the World's Exposition in 1893.