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."

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."

Letter from James E. Frear to John Patterson Osterhout regarding a deed. James told him that he sent along a deed that John needed to sign and have notarized before sending it back. Money would be sent later for the sale of a mill property.

Letter from Ellen Lawson Dabbs to John Patterson Osterhout about her daughter, Junia. She told him how she found the name and that she named her daughter that because she could convince no one else to use that name for their child. She ended her letter by writing that she had gone to Austin, Texas because she was interested in the Girl's Industrial School. Included is an envelope addressed to "Judge J. P. Osterhout."

Letter from Gertrude Osterhout to Osterhout Family. She wrote to update her family about her life at school. She spoke of her school work and upcoming examinations, her concerns about her weight, and a recent death.