Letters, journals, diary and miscellaneous documents created by William S. Prentiss, Roderick Prentiss, William Prentiss, and their descendants. Nine letters were written by Roderick to his brother, William which describe his experiences as a cadet at the United States Naval Academy and an officer serving aboard the United States Naval vessels Portsmouth, Crusader, and Monongahela. The letters describe student life, shipboard incidents, and fellow shipmates in some detail. Two additional letters from Roderick were written to his father, William S. Prentiss, just days before Roderick's death during the Battle of Mobile. These letters describe Roderick's religious conversion and presentment of death in addition to preparations for the upcoming fight. One letter from William S. Prentiss to his wife Mary discusses the aftermath of their son's death, and two additional letters to William S. Prentiss from William B. Lewis and Oliver Ambrose Batcheller, officers on the USS Monongahela, give additional details on Roderick's death. Three bound journals kept by Roderick document his service on the Plymouth, Portsmouth, and San Jacinto. Much of the information in these journals is as detailed as a ship's log, but although often signed by the ship's commander, they do not appear to be the official log for any of the vessels. The overland trail diary of William Prentiss documents his departure from LaGrange Indiana and subsequent journey to the gold fields of Montana Territory. Prentiss traveled with several other men, following a route along the Platte River in present day Nebraska to Fort Laramie. From that point they veered northwest and followed the Bridger Trail from present day Caspar, Wyoming and through the Big Horn basin. After reaching the Yellowstone River they went through the Bozeman Pass and ended their journey at Virginia City. The diary records Prentiss's unsuccessful time searching for gold in Alder Gulch and his decision to return to Indiana after reading of his brother's death in a Salt Lake City newspaper. The route home followed the Virginia City-Salt Lake City trail to Soda Springs, and then southeast to Fort Bridger before again turning east across Nebraska. The diary describes travel companions and trail incidents in varying detail. The collection also includes transcriptions of Roderick's letters, some of his journals, and William's overland trail diary prepared in 1987 by his great-great granddaughter, Carol Opstad Jaeger. A single folder of miscellaneous documents, including an unidentified reminiscence by a Prentiss family descendant, is included. The items in this collection have been calendared by genre and thereafter in chronological order.