Series I. Shipping Papers is comprised of correspondence and ships' papers. The correspondence, which contains merchant and miscellaneous masters' correspondence, traces the development of the Gregory family shipping business from Joseph Gregory's (1755-1824) modest beginnings to Joseph Gregory's (b. 1815) prosperous firm. The correspondence also includes letters from John H. Gregory's partner, Benjamin Selman, and correspondence from company agents or liaisons: Levett Kingsbery in New York City and Albany, Joseph Gregory (b. 1815) in New York, John P. Merriam in Providence, Rhode Island, and Emerson Ames (who married Tabitha Gregory) in Boston. Of interest in the correspondence is an 1826 letter describing the collision of the Gregory's sloop Express with the steamship New Philadelphia, news of Ambrose Gregory's drowning in New Orleans (1831), and 1840 anti-Whig sentiments.

The ships' papers are arranged alphabetically by vessel name, and include ships owned or mastered by members of the Gregory family (see Appendix I). The bulk of these vessels were involved in fishing expeditions and coastwise shipping. Also included, however, are papers of the brig John C. Legrand and the schooner Mary Helen, mastered by John H. (1809-1852) and Thomas Gregory (b. 1821). These vessels transported passengers and supplies to the gold fields of California. Of interest in the papers of the schooner Pacific is Captain Lemon's account of the attack made on him by two crewmen in 1829.

The shipping papers also contain a folder of receipts generated from John H. Gregory's (b. 1793) work as collection agent for 1812 privateer shareholders. In this capacity, John collected portions of prizes from such notable privateers as the schooners Dart, Dolphin, and Growler, and the brig Grand Turk (see Appendix II for listing). Also included is a folder of family correspondence from Michael B., William D., and Thomas Gregory (b. 1821) written while they were seamen or mates at sea (see Appendix III for listing).