Legh Kilpin had been a member of arts organizations in England, and became especially active in Canada as a member of both the Art Association of Montreal and the Montreal Arts Club. Although Kilpin lived only twelve years in Canada, it was perhaps the period of his greatest development and experimentation as an artist. He was also a teacher in Canada, teaching at the Montreal Technical Institute and then in public schools in the Westmount School District.

Kilpin was afflicted with cardiac problems during the last years of his life. On November 4, 1919, after returning from a day of teaching, he died of a heart attack at home in an easy chair, one day before his 66th birthday.