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Barbados & Canada have had strong links (both musical & otherwise) since the 50's. 

Barbados has always (well for well over 100 years) been more 'British' than the UK. Many Bajans fought for us in WW2 & others were amongst the 1st of the Windrush folk, but that's by the by.

Canada was (50's / 60's) also very British but also very cold in the winters (which are about 6 months long). So to escape their winters, many 'better off' Canadians bought holiday homes on the island & spent much of the winter there (towns like Holetown have whole areas of small villas that were built for & bought by Canadians). With lots of Canadians spending 8 to 12 weeks on the island each year, it was only natural that romantic relationships would develop. Many new 'couples' wanted to stay together, so would move to Canada, still spending the winter back in the Caribbean. A two way relationship soon developed & Bajans started to move to Canada for education purposes and more. Many Bajan singers relocated to Canada, which took over from Jamaica & the UK as the No.1 place for musically talented folk to relocate to. Many other local singers did head off to Miami / New York or the UK, but many made Canada their home.

Canada always made it easy for Bajans to move there (unlike the UK) & nearly always made them welcome (unlike the UK). Each year the islanders celebrate CROP-OVER & lots of Emigrants return home to see family members. Lots of the singers , musicians also head back home to perform at the many musical events staged in that period.  

In the 80's & 90's lots of the best 'soul' music to come out of Canada was recorded by Bajans or the kids of ex-Bajans. I know lots of those recordings were highlighted at the time in soul mags like Steve G's New Blackbeat. Sadly, most of that music & those artists slipped quickly back into obscurity.