Letter from Gertrude Osterhout to her father, John Patterson Osterhout, discussing daily life at school. She told her father of her responsibilities to check housekeeping of all the girls' rooms and to keep flirtation between the boys and girls to a minimum. The letter detailed many of the events that Baylor held for its students, including musical recitations and drawing room receptions to teach the girls how to entertain guests. She closed the letter by saying she expected her sister to write soon and that she would write her brother next.

Letter from Gertrude Osterhout to her brother, Paul Osterhout, discussing her life at school. She wrote about her responsibilities of acting as a supervisor for the girls at the boarding house. She told him of the local gossip and school events, including concerts and drawing room receptions where the girls were taught how to entertain guests. A day after she finished the first part of the letter, she continued to write a couple pages more about a recent storm that had hit the city and resulted in property damage and a couple of lives lost.

Letter from Gertrude Osterhout to her mother, Junia Roberts Osterhout, discussing her time at Baylor University. She wrote to her mother about how discouraged she had been feeling lately and that the poor weather outside had her feeling unwell. She asked for news from the family and said she would be writing her sisters soon.

Letter from J. Z. Miller to unknown discussing the work of John Patterson Osterhout. Miller told the gentleman he was writing that John was a respectable judge and had done good work.

Letter from George Robinson to Judge John Patterson Osterhout regarding the trustworthiness of John. The letter is short and simply states that the judge was deserving of respect and was held in high esteem.

Letter from F. M. Law to President William McKinley regarding John Patterson Osterhout applying for postmaster in Belton, Texas. He gives John a high amount of praise and states that he has the support of the administration of Baylor College.

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 wife, Sarah Osterhout, regarding his time in Bellville, Texas. He apologized for not writing her sooner since he has been busy with setting up his business as a lawyer. He was considering purchasing slaves although he mentioned a preference for having "white hands" to work with like he did in Pennsylvania. Recently, his friends had been telling him that he was in a good position to marry and he told his mother that he had someone from Pennsylvania in mind. The rest of his family was offended that he had not written then, but he felt that they read the letters he sent to each of them and that it would be repetitive to write the same thing to all of them. He told his mother not to share this letter with any of them and shared that his lawyer business was going well.

Letter from P. M. Osterhout to his brother, John Patterson Osterhout. P. M. Osterhout wrote his brother about their family and his work with legislation. He briefly mentions a few bills that were being considered, such as an amendment to the civil code.

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout. He was a district judge that was traveling to perform court. He wrote of temperance meetings that were being held in what he considered lawless parts of the country. Pledges were being signed to abstain from alcohol and he told his wife that future temperance meetings were being planned.

Letter from Sarah Hartly to John Patterson Osterhout. Sarah began by writing of the affairs of her boarding house and how many guests she had. The letter is primarily composed of miscellaneous information about various family members and she requests that John take a vacation so that he may visit their parents.

Letter from Paul Osterhout to his father, John Patterson Osterhout, discussing his time away from home at school. Paul wrote that he did not have much news to include other than a death that had happened at the school and that his sister, Gertrude, was doing well.

Letter from Paul Osterhout to his parents, John Patterson and Junia Roberts Osterhout, discussing his time at Baylor College. Paul wrote that the only news he had was school-related and he told his parents about an upcoming lecture and a study group he participated in. He ended his letter by letting them know that the bills to pay for his education was sent home to his parents.

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 Sarah Osterhout to her sister, Junia Roberts Osterhout, and family with local news. Sarah wrote about photographs that had been taken and received, although she has not received the one of herself from the photographer yet. She gave Junia news of marriages and farm repairs. She wrote of a trip she made where she tried to speak to Junia's Congressman and how she tried to speak to the President when she visited the White House.

Letter from Silas O. Osterhout to his cousin, John Patterson Osterhout, about tracing the family line of Osterhout. Silas believed that if they did, they would be able to gain a great deal in inheritance. Included is an envelope addressed to "J. P. Osterhout ESQ."

Letter from A. B. Dickson to John Patterson Osterhout regarding a recent trip to Texas. Dickson planned to buy land in Texas and wanted to speak with John and visit him next time he visited the state. Included is an envelope addressed to "Hon. John P. Osterhout."

Letter from Elizabeth to her brother, John Patterson Osterhout, regarding a death in the family. She wrote that she was grateful she had children to take care of her after her husband died and that once the estate was settled, there would not be anything she could use to take care of herself with. Included is an envelope addressed to "Mr. John P. Osterhout."

Letter from Sarah Osterhout to her brother, John Patterson Osterhout, discussing troubles she has been having. She asked if she could buy his share of land and that money was tight for her. John's son, John Jeremiah Osterhout, and Jeremiah's daughter had succumbed to illness and Sarah wanted to know what her brother wanted to do. In the post-script, Sarah mentioned that her brother had begun a lawsuit against her and wished he would wait. Included is an envelope addressed to "Mr. John P. Osterhout."

Letter from Sarah Osterhout to her brother, John Patterson Osterhout, concerning her difficulties. Sarah had been spending the past several weeks taking care of John's son, John Jeremiah Osterhout, and Jeremiah's daughter, Rua. She was having financial difficulties due to Jeremiah's debt and medical expenses. She needed to send her brother money for property that had been sold, but felt he was asking for too much. Included is an envelope addressed "Mr. John Osterhout."

Letter from Gertrude Osterhout to her cousin, George E. Osterhout, discussing a loan. Gertrude wanted to borrow a few hundred dollars from George and would be grateful if he would lend it. She intended to write him a longer letter when the weather improved. Included is an envelope addressed "Mr. Geo. E. Osterhout."

Letter from D. P. Marcy to John Patterson Osterhout regarding a debt he wanted collected. Marcy had someone who owed him money and requested that John collected the money for him. He then wrote about how his family was doing and that a family member was sick.

Photocopy of a letter from Gertrude Osterhout to her mother, Junia Roberts Osterhout, about her life at school. She mentioned a sociable she was getting ready to attend and how the other girls were worrying about what to wear. She mentioned events that were happening at school, including a music event and lectures she attended. Her brother, Paul, had received a joke Valentine's Day card and she promised to write her younger sister, Junia, soon.