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 Sarah Frear to her sister, Junia Roberts Osterhout, discussing a letter received from sister Amy. She asked Junia how her daughters, Ora and Junia, were doing and asked where they would be next so she could try to visit.

Letter from John Patterson Osterhout to his wife, Junia Roberts Osterhout, and his children about his recent travel. He listed places where he had visited, including arrival and departure times, and told Junia about how her parents and the rest of their family were faring.

Letter from J. Wheelock to his cousin, John Patterson Osterhout, regarding news of his family. Wheelock shared how his family was faring and that their small town was starting to grow. Included is an envelope addressed to "John P. Osterhout."

A brief letter from James E. Frear to John Patterson Osterhout concerning legal matters. It appears there is trouble concerning the death of someone and an estate that had no will. James, an attorney, advises that John sue for his share having been used for a time before everything was sorted out. Included is an envelope addressed to "Hon. John Patterson Osterhout."

Letter from Chloe Smith to her uncle, John Patterson Osterhout, discussing the family. She wrote about how she and her mother were coping with the loss of her father. She told him that his son, Paul, had returned home. Included is an envelope addressed to "Mr. J. P. Osterhout."

Letter from Elizabeth to her brother, John Patterson Osterhout, regarding a death in the family. She wrote that she was grateful she had children to take care of her after her husband died and that once the estate was settled, there would not be anything she could use to take care of herself with. Included is an envelope addressed to "Mr. John P. Osterhout."

Letter from James E. Frear to John Patterson Osterhout regarding an inheritance. James told John he was entitled to one tenth of the money a family member would receive for property that was being sold after someone's death.

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 Sarah Osterhout to her brother, John Patterson Osterhout, discussing troubles she has been having. She asked if she could buy his share of land and that money was tight for her. John's son, John Jeremiah Osterhout, and Jeremiah's daughter had succumbed to illness and Sarah wanted to know what her brother wanted to do. In the post-script, Sarah mentioned that her brother had begun a lawsuit against her and wished he would wait. Included is an envelope addressed to "Mr. John P. Osterhout."

Letter from Sarah Osterhout to her brother, John Patterson Osterhout, concerning her difficulties. Sarah had been spending the past several weeks taking care of John's son, John Jeremiah Osterhout, and Jeremiah's daughter, Rua. She was having financial difficulties due to Jeremiah's debt and medical expenses. She needed to send her brother money for property that had been sold, but felt he was asking for too much. Included is an envelope addressed "Mr. John Osterhout."

Letter from D. P. Marcy to John Patterson Osterhout regarding a debt he wanted collected. Marcy had someone who owed him money and requested that John collected the money for him. He then wrote about how his family was doing and that a family member was sick.

Letter from Mary to her niece, Ora Osterhout, regarding daily events for her family. She wrote that a family member visited her often and that she wanted to know more about a doctor that Ora had mentioned to her. She closed by telling Ora about her health and her daughter in school. Included is an envelope addressed to "Miss Ora Osterhout."