Series II. Correspondence covers the years 1827 to 1903. Subseries A. Letter Books contains originals and copies of letters sent and received from merchant houses and ships' masters; Volumes 32 to 36 include indexes. The telegram books contain messages received by the firm from 1878 to 1890. Loose telegrams are filed with merchant house and miscellaneous business correspondence, subseries D and F. Subseries B. Internal Correspondence contains business letters between the firm members. The correspondence before 1865 relates ships' progress, selection of masters, and cargo importation. Correspondence between George H. Allen and firm members discusses financial transactions and investments. Letters from Silsbee and Pickman to George H. Allen also include letters from the partners' children concerning business.

Subseries C. Agents' Correspondence includes letters to and from Stone Silsbee and Pickman agents: F. W. Brown in Hobartown, Australia; E. A. Emmerton in Manila; and J. Henry Williams in New York. The correspondence in this subseries discusses ships' progress, prices current, and advice for the sale and purchase of cargo. Subseries D. Merchant House Correspondence also discusses ships' progress, prices current, and advice for the sale and purchase of cargo. Also in the merchant house correspondence are a few letters addressed to members of Stone Silsbee and Pickman.

Subseries E. American Business Correspondence reveals the transition of Stone Silsbee and Pickman, from a shipping company to Silsbee Pickman and Allen, an investment firm. Early correspondence with merchants concerns ships' activities, insurance, importation and sale of cargoes, and George H. Allen's ventures in the cigar business. Correspondence after 1870 increasingly concerns investments by firm members. Subseries F. Miscellaneous Business Correspondence covers the years 1855 to 1903.