Wilfrid McGregor was born in Acton, Ontario and moved to Brandon in 1910.  He attended school at Bloomsbury Elementary and Brandon Collegiate. Later he took over his father's farm north of Brandon where he made his home until 1968.

McGregor ventured into public service in Manitoba in 1932 when he became secretary of Bloomsbury School District and where he served for 34 years as secretary and trustee until the district amalgamated with Brandon division in 1966. He served as a trustee of Brandon School district  and division boards for eight years and for more than 10 years was a member of the board of directors of Brandon College, serving as chairman of the board while that institution became Brandon University. He was among the first to be honored by the university with an Honorary Doctor of Laws degree. 

Public service for McGregor took many forms. In addition to his long service as school trustee and university board member, he served the Provincial Exhibition of Manitoba for 20 years, three as president, was president and director of Brandon Consumers Co-operative for many years, a delegate to the local board of Manitoba Pool Elevators, president of Manitoba Co-operative Livestock Association, a director of Manitoba Dairy and Poultry Co-operative and an active worker in the development of the Manitoba Co-op Livestock Market. 

In recognition of his consistent excellence of his community service, McGregor was presented with a 1967 Good Citizenship Award of the Golden Boys of Manitoba.