Letter from E. M. Drayton to President William McKinley regarding John Patterson Osterhout applying for the position of postmaster in Belton, Texas. He wrote that he could think of no one better to fill the position.

Letter from John Patterson Osterhout to his brother regarding land in Texas. He sold a couple hundred acres out of the 400 acres he bought a few years earlier. He wrote about other land he had bought and the cheap pricing of land in Texas. An uncle of theirs was thinking about moving to Texas and John agreed that he should and could get a lot of land for his money. He gave some advice for his uncle if he chose to move to Texas and recommended he should have a few thousand dollars before coming. At the end of the letter, John wrote about several pieces of furniture and cattle he purchased.

Letter from J. W. McDade to Headquarters concerning Private John Patterson Osterhout's detachment. The brief message stated that John was officially detached from his unit and had to report back to his company after seven days.

Letter from Paul Osterhout to his father, John Patterson Osterhout. He wrote to his father because his mother was sick with a cold and unable to write. Paul a brief summary of local news that included recent deaths and a musical performance that was happening soon.

Letter from Sarah Frear to her sister, Junia Roberts Osterhout, discussing a letter received from sister Amy. She asked Junia how her daughters, Ora and Junia, were doing and asked where they would be next so she could try to visit.

Letter from John Patterson Osterhout to his daughter, Gertrude Osterhout, with news from home. Everyone at home at been well, except for her mother who had a cold. They had four cows that they milked and used the milk to make butter to sell. He told his daughter that she should not be so eager for school to be over. He concluded the letter by correcting his daughter on her use of the word "too."

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout, and his children about his recent travel. He listed places where he had visited, including arrival and departure times, and told Junia about how her parents and the rest of their family were faring.

Letter from Alice to her cousins about family news and her schooling. She wrote about the teacher she and her sister have and the state of the school building. She told her cousins that they had to write a return letter or she would not write them again.

Letter from John M. Garman to John Patterson Osterhout regarding an invitation to visit Belton, Texas. Mr. Garman regretted having to decline Mr. Osterhout's invitation to visit and told him that the next time he came South, he would try to visit. Included is an envelope addressed to "Hon. J. P. Osterhout." The front of the envelope has an image of the lobby at the New Waverly Hotel and Bath House in Hot Springs, Arkansas.