Documents pertaining to Milo Kendall's law practice and other business dealings. The majority of the law papers are from Kendall's partnerships with Owen G. Lovejoy and George O. Ide (1857-1871), and cover a variety of issues, including land and property agreements and disputes, estate administration, divorces, and debt collection. Kendall managed debt assignments for two associates, Elijah Dee and Benjamin Newell, working out payment schedules with creditors for both men. There are legal documents such as wills, deeds, mortgages, and leases included in the papers, as well as hand-written depositions and briefs. Kendall served as lawyer for both the Chicago, Burlington & Quincy Railroad and the Illinois Grand Trunk Railway (formerly the Camanche, Albany, and Mendota Railroad), and there are materials related to personal injury cases as well as right of way and securities issues. Some of the business correspondence overlaps with materials in the legal documents and cases series.

Kendall was also involved in real estate ventures in Princeton. He bought, sold, and leased property himself and also entered into a partnership with local businessmen Jacob T. Thomson and Joseph V. Thompson to buy 100 acres of land in the northern part of Princeton, which they then divided into lots and sold. Other materials include a small amount of materials from Kendall's first law partnership with C.K. Harvey in 1846, expense logs and receipts from Kendall's later law practices, land abstracts, copies of documents Kendall notarized, and financial records of the American House Hotel in Princeton, which Kendall had an interest in.

The ledgers are primarily copies of documents from the later years of Kendall's law practice & business dealings, and continue into 1911 when his son William I. Kendall took over. However, the first ledger, 1860-1890, contains receipts and original business correspondence, and also serves as a scrapbook as it includes newspaper clippings and personal correspondence. Of note is a letter Milo Kendall wrote to his last surviving brother Alonzo Kendall, in which he reminisces about the family's early life in Vermont.