Annual Bajan Night in Winnipeg
Annual Independence Banquet and Dance
Initially, The Annual Independence Banquet & Dance was seen as the premier function of the Association's social calendar and was the leading fund-raiser. Gradually, however, it ceased to be lucrative, even though it often attracted some important personalities from Bridgetown and Ottawa. In 1981, for example, the keynote speaker was the Hon Mr Lindsay Bolden, a member of the Barbados Labour Party cabinet. In 1984, it was the Hon Mr Louis Tull, Barbados' Minister of External Affairs, who gave the keynote speech; and in 1982, His Excellency Mr Lester B. Whitehead Barbados' High Commissioner to Canada, delivered the feature address. 
Annual Picnic 2012
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The Support from the wide circle of friends accumulated by the Association over the years has been reflected in the number of tickets routinely sold for the vast majority of its functions. Since the late 1980S, Bajan Nights of the period 1989-94 were phenomenally successful. Approximately 300 attend the Norwood Community Club in 1988, when Mr. Austin "Tom" Clarke, a famous Barbadian-Canadian author, read from his short stores; and almost 500 were present at the Franco-Manitoban Centre in 1989.

The Bajan Night Festival, usually held on the third Saturday in June, has become the biggest event on the Association's annual calendar. It involves careful planning, optimistic budgeting, and the wholehearted cooperation of almost all its members. In 1989, in addition to Bajan cuisine, the event featured art, drama, comedy and music.

Barbados Association Banquet 2010
Bajan Night 2012
Annual Picnic 2013
Barbados Association Banquet 2012
Bajan Night 2015

Barbados' 50th Anniversary
Independence Banquet & Dance
November 2016
Bajan Night 2016
Bajan Night 2017
The Barbados Association 40th Anniversary
Banquet & Dance 2017
Bajan Night 2018

Barbados Association Banquet 2018