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.