Harry Britton was born in Cambridge, England. His family arrived in Canada in 1881 and settled in Toronto. Between 1902 and 1908, he intermediately studied art with Farquar McGillivray Knowles in Toronto.
He became a member of the Ontario Society of Artists in 1903 and started exhibiting with the Royal Canadian Academy in 1905, which he did almost annually until 1946.
In 1907, he was elected an Associate of the Royal Canadian Academy.
In 1908 he went back to England and studied at the Heatherley School of Fine Arts in London (1908-1909) and at the London School of Art (c.1909-1911).
During his stay in England, he kept bonds with the Canadian art scene, still exhibiting with the Royal Canadian Academy and participating to the Art Association of Montreal shows of 1909, 1910 and 1912.
In England, Britton gave classes in St.Ives, Cornwall and had Henrietta Hancock as one of his students, who he later married. They stayed in England until 1914 and then came back to Canada where they settled in Toronto.
In Toronto, Britton gave private classes in order to earn additional income. Between 1914 and 1921, he taught to various artists, some of which obtained future success such as A.J. Casson.
In 1921, he and his wife moved back to England where they stayed until 1925. While in Europe, they took the opportunity to travel to France, the Netherlands and Italy.
Upon their return from England, they settled in Nova-Scotia until 1934, year when Britton was made a full-member of the Royal Canadian Academy. They later moved back to Toronto, where they kept busy painting and exhibiting their work.
Britton died in Toronto at the age of 80.