Joseph Paul Keeler Sr. came west from Winnipeg in 1903. In 1904 he established a post office about five miles north of the current town site. The post office was named Keelerville. In 1905 a school, with the same name, was built two miles southwest of the post office. Settlers came to the area from eastern Canada, the US, and England. Between 1906 and 1909 the railroad came through the region connecting Moose Jaw to Outlook. Four grain elevators were built along the rail line. It wasn’t until 1908 that the first building was built in Keeler. The post office was moved into town that year. Around 1909 the Presbyterian Church was established in the town. In 1911 a second school, Keeler School, opened in town. The Keelerville School remained open until 1959. In 1970 Keeler School closed as well.
The peak population of Keeler was 115 in 1926. Keeler’s population began to decline in the 1930s and 1940s due to the Depression and war. It has been the home of less than fifty people since 1981 and today has not more than fifteen. The grain elevators were destroyed in 1978, two in 1986, and the fourth by the early 1990s. In 1988 the rink was demolished and in 1993 the post office closed.
Keeler has an interesting past. Dr. Redmond who served the town from 1916 to 1920 mysteriously disappeared. Secondly, there is speculation that in the 1920s a laundry run by Sam Hing served as a brothel. In 1927 the village communicated with the Moose Jaw police to ask for assistance in problems of bootlegging in the town.