Ashland, on State Highway 154 fourteen miles southeast of Gilmer in extreme southeastern Upshur County, was established around 1845. In antebellum Texas the settlement served as a shipping and marketing point for plantations along the bend of Cypress Creek. A post office under the name Asbury opened there in 1894. By 1896 the community had a sawmill, a general store, Baptist and Methodist churches, two doctors, and an estimated population of 110. In 1902 the community was renamed Ashland. At its height around 1914 Ashland had a bank, a Masonic lodge, four general stores, a cotton gin, and a population of 250. After World War I, however, the town began to decline. The post office was closed in 1921, and by 1933 the population had fallen to 175. In the mid-1930s the community had a church, a store, and a number of scattered houses. By 1945 the population had fallen to twenty. In the mid-1960s Ashland had a church, a cemetery, and a few houses. In 1990 the church and cemetery were still at the site, and Ashland was a dispersed rural community with an estimated population of twenty. By 2000 the population had grown to forty-five.