Letter from Gertrude Osterhout to her mother, Junia Roberts Osterhout, regarding her remaining time at Baylor University. Gertrude was eager to return home and help out around the house. Commencement was fast approaching and she wrote to her mother about what she was going to wear and that she needed her mother to send a few items to make sure she was prepared.

Proof of payment by John Patterson Osterhout for the military service of John N. Robinson. The money was due to Eliza Bennett and was paid in full. The payment was signed and dated by John Ridens.

Letter from S. Harford to John Patterson Osterhout. He wrote to thank John for his advice on business and requested information about moving to Texas. Harford was interested in a location that was free from Indian raids and would allow him to start up a land agency.

Letter from C. F. Hurlbut to John Patterson Osterhout. He wrote John to find out whether or not John still lived in Belton, Texas. Hurlbut wished to receive news of how John and his family were doing. Included is an envelope addressed to "Hon. J. P. Osterhout."

Letter from John Patterson Osterhout to his son, Paul Osterhout. John wrote to his son from his visit with his mother. He mentioned a few land deals he wanted to look into and that his mother offered to give him his father's old desk. John showed interest in starting up a sheep ranch. In the post-script, John said that an aunt might not have much longer to live.

Letter from Paul Osterhout to his father, John Patterson Osterhout, about upcoming events while he was at Baylor College. He wrote about how the boys would be giving speeches at commencement and he planned to praise one of the professors in his speech to increase his chances of winning a medal. Paul requested that his father send him money for new shoes to wear for his speech and listed out his upcoming expenses.

Letter from Paul Osterhout to his sister, Gertrude Osterhout, with news of what he intended to do next. He planned to take a commercial class to learn book-keeping in New York and received a Valentine from an unknown suitor in Independence, Texas. He also wrote about his work and other gossip.

Letter from Mary Chamberlin to Paul Osterhout regarding a photograph that was sent to her. She thanked him for it and asked if his sister, Gertrude, would be able to come down for a visit. Included is an envelope addressed to "Paul Osterhout."

Letter from John Jeremiah Osterhout to his brother, Paul Osterhout, updating him on events at home. John regretted not writing sooner and mentioned an expensive wedding that was being planned in Belton, Texas. He told Paul that he was well and that some of their mutual acquaintances had arrived in town.

Letter from John Patterson Osterhout to his son, Paul Osterhout, regarding Paul returning home for a visit. John recommended Paul get his certification to practice being a doctor before he graduates. John sent what money he could and if Paul was able, he had a list of people he wanted Paul to try to visit.

Letter from E. A. Osterhout to John Patterson Osterhout asking if family John was a part of the New York state family. He told John the name of his father and grandfather and that he would be interested in hearing from him again. Included is an envelope addressed to "Hon. J. P. Osterhout."

Letter from Ora Osterhout to her family regarding her arrival at Austin. She detailed her trip down there and told her family that she had arrived safely. Ora enrolled in the local university after she settled into the boarding school. Included is an envelope addressed to "Mrs. J. P. Osterhout."