Since its inception in 1919 the Festival has grown in size and scope. The first Festival had 274 entries in the 38 classes offered, with a total of 2500 participants. The 87th Annual Festival, held from February 24 to March 20, 2005, had over 3000 entries in more than 500 classes. Running for 23 days, the festival utilized 15 venues in Winnipeg and engaged 15 adjudicators from across Canada. 

The Winnipeg Music Festival was established by the Men's Musical Club, the first festival being held in May 1919. One of the major hurdles for these organizers was selling the idea of a competitive festival to a new market. One solution was to cooperate with existing festivals in Alberta and Saskatchewan, thereby hiring well-known and distinguished musicians, most from Great Britain, as adjudicators. This established a tradition that lasted until the mid 1960s when the festival began selecting adjudicators from North America.  

On the last night of the first festival, the final class lasted until after one in the morning, while the audience of 500 stayed until the adjudication was completed. Interestingly, this last night of the four-day Festival was May 15. The Winnipeg General Strike had begun an hour prior to the completion of this last class and most of the people in the audience walked home because street cars had gone out of service.

The Winnipeg Music Festival has a reputation for the high standards of excellence that it encourages. Participants come from all parts of the Province of Manitoba, from north-west Ontario and from the northern United States to compete in Winnipeg's Festival. Indeed, many internationally known artists have developed their talents at the Winnipeg Music Festival - to name a few: Emmanuel Ax, Tracy Dahl, Douglas Finch, Irena Welhasch, Tom Wiebe, Philip Ens, Valdine Anderson, Chantal Kreviazuk and Loreena McKennitt.