Postcard from Rose Chamberlin to Ora Osterhout. The photo on the card depicts a horse, a cow, and a man. The cow has a rope around one of its horns and the other end is tied to the saddle on the horse. The man is standing with one foot on the cow and both hands in the air. He is wearing a cowboy hat, a shirt over a white one, pants, and dark boots. The scene is in the middle of a prairie. On the bottom of the front and the back, Rose wrote bits of local news.

Letter from John Patterson Osterhout to his son, Paul Osterhout, regarding Paul's return home. John sold Paul's bike and sent him money to help him afford the trip home. John expects his other son, Jeremiah, and his wife to have a child soon because she has been staying with their family for long periods of time. John mentioned that their town, Belton, was worried that their oil well would leave town and they would have to rely on the college for their future.

Letter from John Patterson Osterhout to his daughter, Gertrude Osterhout, discussing daily life at home. He mentioned that they would be able to make some money by producing buttermilk and that they would be getting more poultry soon. John's uncle, Peter, was having a birthday soon and he requested that Gertrude write a letter to him so that he may pass it along. The letter closed with John saying that it was his birthday the next day and that he wanted Gertrude and his son, Paul, to write to him.

Letter from Junia Roberts, John Jeremiah, and Paul Osterhout to John Patterson Osterhout. The letter started out with Junia writing. She wrote very briefly about how she missed her husband. When she had to tend to the baby, her and John Patterson's son, John Jeremiah, finished writing the letter. He told his father how the hogs, cows, and sheep were doing and that they had purchased more corn and cotton-seed for the animals. On the back of the letter, Paul Osterhout, the eldest son, finished writing the letter. He mentioned a man who had been arrested for murder and that the accused was out on bail. In the post script, Paul asked if he could have a party for his 16th birthday.

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.