The original Music Gallery was located at 30 St. Patrick St., near the Ontario College of Art (now known as OCAD) and Art Gallery of Ontario. In 1984, the MG moved to 1087 Queen St. W., in the basement of what was once West Toronto's first YMCA, and is now the Great Hall (the Theatre Centre currently occupies the former MG space). The Music Gallery's "heyday" began in 1991 with the opening of the fabled multi-purpose space at 179 Richmond St., a strange oasis for creativity and experimentation on the outskirts of Toronto's uber-commercialized "entertainment district." Under the direction of Jim Montgomery, who assumed the artistic directorship in 1987, the Richmond location hosted up to 150 concerts a year.

This era came to a sad end in the year 2000, when the Music Gallery became a victim of gentrification: the building's landlords invoked a "demolition clause" and evicted them to make way for, predictably, condominiums. Montgomery and co. were driven to survive, however, and mounted a "Guerrilla Gallery" year for the 2000-01 season, in which MG events happened in various alternate venues throughout the city. The following year, they settled on a new arrangement with the parish of St. George the Martyr Anglican Church, which allowed the MG use of the space for concerts at a reasonable rate, in return for helping the church manage the rental of its hall. Located at 197 John St., at the southern end of Grange Park, the church returns the Music Gallery to its geographical roots.