Photocopy of a letter from Gertrude Osterhout to Paul Osterhout. She wrote her brother and told him of all the talking that goes on in the church she attended and how concerned she was that she'd begin to pick up the slang used by her peers. She also requested that Paul send her some items she could not get locally.

Postcard from Rose Chamberlin to Junia Roberts Osterhout. The front has four photos. The first depicts two men on horses and one of the horses is at the start of a jump. In the second photo, there's one man on a horse galloping. The third has two men on horses and one of the men appears to be getting up to stand on his. In the corner, there's a small circular photo of a man on a horse as it is jumping. All of the scenes in the photos are in a prairie setting. On the bottom of the front and back, Rose wrote about school buildings that were being built, an upcoming fair, and other small bits of news.

Postcard from J. H. to Junia Roberts Osterhout. On the front are a printed border and a quote "What others say of me matters little, what I myself say and do matters much. - Elbert Hubbard." It is printed with some flourishes. On the back J. H. wrote wishing that Junia's art was going well and to send love to Junia's sister, Ora.

Letter E. Walker to George W. Wade telling him that he will probably not be sued. Mr. Walker does not mention why Mr. Wade might have been sued.

Letter from C. B. Wade to Charlie discussing the possibility of a railroad being built from Dublin, Texas, a recent fire, and other recent news. The letter is written on The Hamilton National Bank letterhead. It appears that someone practiced handwriting on the back of the first page, and there is a note written to Mr. Wade from Mrs. John Bevry, [?] Jr. on the back of the last page.

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 Junia Roberts Osterhout to her husband, John Patterson Osterhout. She wrote to him about how she and their children had been doing and mentioned letters she had written and received recently.

Letter from Harry Frear to his cousins, Ora and Junia Roberts Osterhout. The brief letter explained that Harry mistakenly opened a letter that was meant for someone else. He told the girls that he missed them and hoped they could visit soon.

Letter from Paul Osterhout to his parents, John Patterson and Junia Roberts Osterhout. He thanked his family for a recent letter he received from home. Paul described parts of a composition he prepared to give at a commencement ceremony and sent his father a copy of the speech. He mentioned some activities that were going on at the school, including a baseball game and a concert, and insisted that his father or mother try to visit. Included is an envelope addressed to "J. P. Osterhout."

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.