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The small Saskatchewan community known as Ogema and its surrounding community got its first settlers in 1908. Most of those settlers came from the Bruce and Auron county regions in Ontario, but a few came from other parts of the world, including the United States, Europe and the British Isles. The inaugural homesteaders of the land selected “Omega” as its name. “Omega” is a Greek term for the word “end.” The settlers chose this name because, at the time of settlement, it was “the end of the rail-line.” However, when it came time to register the name, a town with the exact same name was unearthed. So it came to be that one letter in the original name was changed, and “Ogema” was born. Ogema is an Anishinaabemowin (Ojibwe) word meaning “Chief.” During the early years of settlement, several modes of transportation were used. Along with walking, a people traveled by horseback, wagons, democrats, buggies and sleighs for the winter.

Living quarters were prepared by the men, who led ahead of their families to make sure the homestead was ready. Power to these homesteads was supplied by oxen, mules or horses. The horses were fed with grain obtained through threshing. The seeding was done with wooden box drills. Threshing time was very exciting for the people of Ogema, as it was seen as the payoff for a year's worth of homesteading.

The period of 1911 to 1913 was a fascinating time for the settlement. First, in February 1911, Ogema was declared a village on the west 1/2 at 22-7-22. On August 10, 1911, the Canadian Pacific Railway line between Assiniboia and Weyburn reached Ogema. The next year was even more exciting, with a telegraph line reaching the village, construction of the first curling rink, and the village's first official sports day being held on June 12. On July 5, 1912, lumber yard manager Raymond Kenneth Rounds co-ordinated a census which concluded that there were 540 citizens living in the village. On October 4, a motion of council proclaimed “Be it resolved that secretary-treasurer post up notices of the intention of village council to apply to the Lieutenant-Governor in Council for the corporation of the village into a town.” In December, Ogema officially became a town. On February 8, 1913, elections for council were held for the newborn town and A.R. Sargent was named mayor.

The year 1914 marked the beginning of the First World War and the town's men were quick to enlist in the military. They quickly sold or rented their homesteads and went off to war. Disaster struck the town in January 1915 when a fire broke out on the east side of Main Street and destroyed nine businesses. Below zero temperatures contributed to the freezing of the fire engine, and so it was of minimal use when it came to extinguishing the fire.

As the war wound down, the town struggled to adjust as the men returned home from the battlefield. Due to injuries sustained while fighting, some of the men could no longer do farm work and had to find other jobs. Also around this period, a flu epidemic seized the town and wiped out entire families.

Eventually, though, the returning soldiers settled into their new jobs and the epidemic passed, giving the people of Ogema renewed hope for the 1920s.