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In 1889 the pioneering Story family from Ontario arrived at the high bank of the Souris River valley and decided that they would never find a more beautiful place to settle.They unloaded their wagon and pitched a tent. This was the beginning of a settlement they called Sipiweske.

The Story's were very progressive and enterprising. They built a general store and many businesses and homes soon followed to serve the surrounding farm community. Homesteading began in 1879 and farmers were eager to support services close to home resulting in a building boom in the village.

In 1898 Mr. Story had a larger general store constructed with living quarters above. This still serves as the only grocery store for the village today. The temperance movement was a factor in having the name of the village changed to Wawanesa, believed to mean "call of the whip-poor-will" in Cree.

The village was incorporated in 1909 and has had a consistent population in the 500's.