Letter from Gertrude Osterhout to her mother, Junia Roberts Osterhout. She wrote her mother to update her about her life at school. Among the small bits of news Gertrude gave, she mentioned a musical performances that the girls gave, a memorial service, and upcoming examinations.

Letter from Gertrude Osterhout to her brother, Paul Osterhout, discussing her life at Baylor University. She told him that her examination scores had been excellent and commencement would be taking place later this year. She wrote of some of the events that the school held including debates, concerts, and essay readings. A storm had passed through her town recently and she told her brother that she would refuse to sleep on the third floor of the boarding house should she return. The letter concluded with a promise of gossip in her next letter and her sympathies that Paul has a night job. Included is an envelope addressed to "Mr. Paul Osterhout."

Acceptance card for the National Society of the Daughters of the American Revolution for Ora Osterhout. Her membership was officially accepted March 6, 1906 and is missing the signature of the recording secretary general.

Application for membership to the National Society United States Daughters of the American Revolution for Ora Osterhout by claim of her relation to Jeremiah Osterhout. The application details her genealogy and Jeremiah's service during the American Revolution.

Letter from May Patterson Frear Osterhout to her sister-in-law, Ora Osterhout, with information on the Osterhout genealogy. The information was gathered from the Carnegie Library in San Antonio, Texas and contains information on various family members.

Letter from Harry Harris to President William McKinley regarding John Patterson Osterhout running for postmaster in Belton, Texas. He endorsed John's run for office and told President McKinley that the appointment would be favorable.

Letter from L. G. Lattimore to President William McKinley regarding John Patterson Osterhout applying for the position of postmaster in Belton, Texas. Mr. Lattimore praised John and stated that his appointment to postmaster would be looked upon well by residents of Belton.

Letter from J. C. Crain, the chairman of the 19th Senatorial district in Texas, to President William McKinley regarding John Patterson Osterhout applying to become the postmaster of Belton, Texas. Crain wrote of how highly he thought of John and recommended him for the position.

Business card for John Patterson Osterhout, an attorney and collector of claims for Austin and surrounding counties. On the back of the card is a note concerning that if money was collected from a claim, it would be paid to someone while John would retain half as commission.

Letter from John Patterson Osterhout to his mother, Sarah Osterhout, regarding his time in Bellville, Texas since his recent move there. He was undecided about whether or not he would remain in the county or travel around Texas. He wrote about how sparse buildings were where he lived and that the way wealth was measured there was not by amount of land, but by the amount of slaves owned. Many in the area had begun growing their own gardens and he had learned from them that he needed to be careful of poisonous spiders and centipedes. John told his mother that the mail was arriving with irregularity and they were lucky if they got it once a week.

Letter from P. M. Osterhout to his brother, John Patterson Osterhout, discussing news from home and slavery. After providing John with updates from those at home, he told his brother he was unsure whether or not he would want to receive something from the black Republican in Pennsylvania. He then went on to write about his opinion on slavery and he hoped his brother was not beginning to view it as a blessing.

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 Libbie to her aunt, Junia Roberts Osterhout, about life in Scranton, Pennsylvania. Libbie wrote of a recent, elegant wedding she had attended and some of the fashion she had been seeing recently. At school, she got held after for breaking one of the rules. The letter closed when it became too late for her to continue writing. Included is an envelope addressed to "Mrs. J. P. Osterhout."

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout. He wrote to inform his wife of his work in the courts and informed her that he might be returning home soon.

Letter from Junia Roberts Osterhout to her husband, John Patterson Osterhout. She wrote how ill she had been feeling recently and how much she and their children have missed John while he has been gone. An envelope addressed to J. P. Osterhout is included.

Letter from M. A. DeWitt to her sister, Junia Roberts Osterhout. She wrote to tell Junia what her children and mother had been up to recently. She mentioned her children's education and other bits of local news. An envelope addressed to Mrs. J. P. Osterhout is included.

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout. He wrote a short letter to his wife to inform her that he hoped to be finished with his work as a judge soon and wished her and their children well.

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout. He wrote his wife to inform her that he was almost done with his work in the courts and that he planned to return home soon. An envelope addressed to Mrs. J. P. Osterhout is included.

Letter from Junia Roberts Osterhout to her husband, John Patterson Osterhout. She wrote John to tell him how she and their children were doing while he worked out of town.

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout. He commented that he had not received letters from home recently and wished to receive news from his wife. John purchased a pony for their son, Jeremiah, and planned to have it sent back while he continued to travel for business.

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."

Postcard from John Patterson Osterhout to his son, Paul Osterhout, regarding requests from others that he was passing along. A doctor wanted Paul to look up where and for how much he could obtain a couple of books. The doctor was also waiting on Paul to let him know what the cost would be to get to where he was.

Letter from W. W. Culver Jr. to John Patterson Osterhout regarding recent events. Culver told him that he had been very sick, but had recovered and that he was going to see an acquaintance of John's daughter. Included is an envelope addressed to "J. P. Osterhout Esq." and there is an image of a steel range and furnace.

Letter from James E. Frear to John Patterson Osterhout regarding inheritance money. James sent a draft for less than $400 and told John that he would continue to look after his interests in these affairs. Included is an envelope addressed to "Hon. John P. Osterhout."