Arriving in Winnipeg in 1913, Walter and Gladys eventually settled in the north end of the city. Walter was soon busy teaching at a secondary school and continuing his work as a watercolour painter. He soon discovered new subject matter in the suburbs of Winnipeg, and the family spent its first summer at Lake of the Woods on the Manitoba-Ontario border in 1914. He met other artists then working in Winnipeg, such as Cyril Barraud, a fellow-Englishman who had come to Winnipeg a year earlier, and was now engaged in etching. Phillips and Barraud held a joint exhibition in Winnipeg in October of 1914.