In 1888, Sheffield Peabody was struggling to afford his farm and was in debt to several of his neighbors. Sheffield, with the help of his oldest son, George L. Peabody, decided to sell some of his property. Even this effort could not save his farm and support his large family. Peabody decided to move to Oklahoma, where he knew land would be available and he could work and make more money. Unfortunately, Peabody could not take his family with him to Oklahoma; he would have to leave them behind. Starting in March of 1889, President Benjamin Harrison issued a proclamation of 1,887,796 acres in the state of Oklahoma. Towards the end of April, Americans rushed to Oklahoma to make claims for land. Cities began to emerge in Oklahoma City, Kingfisher, El Reno, Guthrie, and Stillwater. On May 1, 1889, Sheffield made his first land claim for Oklahoma territory, near the town of Edmond, which would be his home base for the next six years. During his stay in Oklahoma territory, Sheffield would travel to the cities of Oklahoma City, and Guthrie.
Similar to his life back in Springwater, Sheffield Peabody worked hard and was very mobile. He set up a contract to work on the railroad that ran through Oklahoma. His work consisted of setting, cutting, and transporting posts. He made frequent trips up to Edmond for errands such as groceries and clothing items. He also participated in the local events such as elections and the Decoration that were held in Edmond. Despite not having his family to comfort him Sheffield, maintained most of his normal routines of attending church, dining with friends and participating in school board meetings.
Although Sheffield remained active and focused on his work, we can infer that he felt isolated from his family. He traveled a great psychical distance between Springwater, New York and Oklahoma. Sheffield would travel 1500 miles from Springwater New York to Edmond, Oklahoma. In addition, there was a lot of emotional distance between him, his neighbors, and family. Sheffield writes, in the back of his diary for 1894, “I have no family. Am alone, and care for myself". Sheffield made frequent trips to the post office to send and receive letters. Between the years of 1894 and 1895, Sheffield indicates that he went to the post office 32 times to. He mentions receiving letters from his daughter, Emma in August of 1894 and his family on December 30 of 1894. The letters indicate that Peabody was in communication to his family, however in a very restricted way. Before Peabody moved to Oklahoma he used to mention his family all the time, during his stay in Oklahoma he only mentions receiving two postcards. Thus revealing how the circuit between Peabody and his family was fragile.
—"Rushes to Statehood, The Oklahoma Land Runs". Dickinson Research Center. Retrieved 2015-04-25.