Glenwood, at the junction of State Highway 300 and Farm Road 726, eight miles southeast of Gilmer in southeastern Upshur County, was established as a plantation before the organization of the county in 1846. The plantation was abandoned before the Civil War, and during the last years of the war new settlers began to move to the area. A post office opened there in 1875 with Wiley Florence as postmaster; he apparently named the town. Just after the war a Glenwood Methodist Church was established, and around the same time a school began operating in the church. Charlie Christian opened a local boarding school in 1880. By 1885 Glenwood had a steam gristmill and cotton gin, a general store, two churches, and an estimated population of 100. The town continued to grow during the 1890s and early 1900s, and by 1914 it had reached a peak reported population of 250. After World War I, however, the community began to decline. Its post office closed, and by the mid-1930s Glenwood comprised only a church, a school, a store, and a number of houses. In 1940 its population was estimated at ninety. After World War II the Glenwood school was consolidated with that of East Mountain, and in the mid-1960s all that remained of Glenwood was a church, a store, a cemetery, and a few scattered houses. In 2000 Glenwood was a dispersed rural community with some 150 inhabitants and a community center on Farm Road 726.