Settlers began arriving in the Winkler area in 1846, and by the 1860s several farms were in operation. Settlement increased after the Civil War, and the town was organized in 1879. Because of its location, the community was part of both Navarro and Freestone counties. With W.S. Grayson as postmaster, a post office was established on April 28, 1879, on the Freestone County side and was named for Clinton McKamy Winkler, a Confederate veteran, county judge, and state legislator. Within a year, the town had several homes and businesses. The coming of the railroad caused population shifts, including movement from Winkler to the new town of Streetman in 1905. Winkler nevertheless continued with a small population, and its post office remained in operation until 1973. The Winkler County Line Common School District was created in 1896. Classes met in homes until 1898, when Dr. T.B. Grayson donated land for a combination Masonic Lodge, school, and church. Winkler Baptist Church was organized on January 16, 1898, with C.C. Lee as its first pastor. Before 1940, businesses in Winkler included grocery and mercantile stores, blacksmith shops, and gins.