It was founded by Alonzo Fowler Kempton, who started the company using money invested by local farmers.

After two weeks, Charles Kerr, Alonzo's partner, completed the company's first policy, insuring a thresher for $600 at a premium of $24 for three years.

[7] In 1901, Wawanesa moved to a new building overlooking the Souris River valley, and the number of employees increased to five.

[8] During the Great Depression, Wawanesa expanded, fueled by large cash reserves and new offices in Vancouver, Toronto, Montreal, Winnipeg, and Moncton; however, the company was forced to cut director's salaries by 20 per cent, and on corporate visits, the company directors shared beds.

[8][10] In 1975, Wawanesa's United States branch was established under the laws of California,[12] making it the first Canadian general insurance company to successfully enter the US.

In 2020, Wawanesa opened a head office for the San Diego location, although they also write automobile policies in the state of Oregon.