This collection includes three series of papers of Henry C. Wysor and his family members. The first series comprises personal correspondence sent to Henry C. Wysor, his wife Mary E. Wysor who is sometimes referred to as Mrs. Henry C. Wysor, and his daughter Mary S. Wysor. The second series consists of papers regarding Henry C. Wysor's two businesses, his Apple Orchard and Life Insurance Branch. The Apple Orchard papers include correspondences and ledger paper sheets. The Life Insurance Branch consists of correspondences from the insurance company and clients inquiring about their policy or making payments. The third series consists of personal papers from Henry C. Wysor and his son Henry Wysor. There are two handwritten agreements between Henry C. Wysor and others. Henry C. Wysor Writings contains letters written by him and short stories. His personal invoices and receipts are also included in this series.

In Series I: Personal Correspondence, there are three subseries of correspondence. These letters contain details that are personal to the family members, rather than focusing on the business endeavors of Henry C. Wysor.

The collection contains many letters addressed to Henry C. Wysor from his wife, sons while they attended Virginia Tech, his daughter Mary S. Wysor, family members, and friends. Some letters briefly discuss business and job opportunities, such as one letter explaining, "I have secured a job with Mr. Janney in the Wells Branch Coal Co. 3 miles above Dunlow [West Virginia]." Others discuss family health concerns, such as "Mary's illness. I know you are anxious about her. She will soon be her usual self." Another letter contains information on Henry purchasing a train ticket with Southern Railway Company. He also received letters from his son Henry Wysor who worked as a prfoessor at Lafayettel College in Easton, Pennsylvania. One letter discusses the apple orchard, and he inquires about "the news in last nights and todays papers of the Hillsville affair. Judge Massie is the only one of the victims whose name I recognize as one of our old citizens of Pulaski. I trust ... speedy arrest and punishments of these murderers." Later letters inform from Henry to his father discuss how his children Henry and Elizabeth have the whooping cough.

There are many letters addressed to Mary E. Wysor, or Mrs. Henry C. Wysor. Many of these come from her children. Many letters arrive from her son Henry Wysor in Duquesne, Pennsylvania. She often received letters from her husband during his travels. With one letter, he included a short story titled, "Little Corners." Throughout 1905, she received many letters from Henry during his travels, and he sent newspaper clippings to her. The subseries includes a wedding invitation and a graduation invitation.

The daughter Mary S. Wysor received letters over the years. She often received letters from friends around the Pulaski area and from her brothers. Her brothers addressed her as "Sitta." One of her brother's letters discusses their father's apple orchard business where he explains how someone purchased the apples but did not have enough for apple butter.

In Series II: Business Papers, there are papers related to Henry C. Wysor's apple orchard business and life insurance branch business. The apple orchard business contains correspondences and individual ledger papers. Correspondences relate to the harvesting, seasons, and details of the orchard. The life insurance branch was part the New York Life Insurance Company, and Henry C. Wysor had a branch in southwestern Virginia. Many correspondences relate to policy payments and loans. Other correspondences discuss policy applicants for branch. Others discuss the policy options and promote the policies to individuals considering the work.

In Series III: Personal Papers, there are multiple types of papers such as handwritten agreements, short stories, and invoices. One agreement is between Henry C. Wysor and James M. Miller, and the other between Henry C. Wysor, James M. Miller, John B. Baskerville, and George W. Wysor. Henry Wysor wrote an outline for one of his classes at Virginia Tech. Henry C. Wysor's writings are placed together, including letters he wrote and short stories. Both of his short stories relate to the Bible. Some letters are written for his children and family, rather than individual family members which is why they are located with henry C. Wysor's writings. The invoices and receipts deal with his personal purchases.

Box 5 also contains the original collection notes with brief 1-2 sentence descriptions of majority of the letters. Print outs from ancestry.com are also found in this folder.