While the Parade of Bands is the most-well known festivities, events vary per year and in the past has included exhibits (for example the first Caribana displayed every book published by a Caribbean writer, including Austin Clarke who was the centrepiece of the exhibition); theatre plays (such as Austin Clarke's "Children of the Scheme" which dealt with the plight of Caribbean women who came to Canada on the domestic immigrant worker scheme); and fashion shows.

The street Parade of Bands consists of costumed dancers (called "Mas players") along with live Caribbean music being played from large speakers on the flat-bed of 18 wheeler trucks.

[5] In competition with one another during the parade, they pass a judging spot which will rate each band section for its costume design, the energy of masqueraders, the creativity of presentation and so on.

In the 1970s, the parade route originally followed Bloor and Yonge Streets ending at Toronto City Hall concluding with a concert at Nathan Phillips Square.

Spectators and or persons "playing Mas" will occasionally get themselves covered from head-to-toe with mud, flour, baby powder, or different water-colored paints in the tradition of the Caribbean-based J'ouvert celebrations.

Billing itself as a multicultural nation, the Canadian government invited ethno-cultural groups to contribute celebrations with representations of their ethnic diversity.

[28] Caribana emerged during a time when many Caribbean residents emigrated to Canada following immigration reform, internationally acclaimed singers were popularizing Caribbean music (for example Harry Belafonte sang to a sold-out crowd at the O'Keefe Centre in Toronto), Civil Rights Movement activities including the Canadian visits by Malcolm X and Martin Luther King Jr., and Muhammad Ali's fight against the Canadian heavyweight champion George Chuvalo.

[33][29] From 1952 to 1964, CANEWA produced, funded, and hosted these annual one-day celebrations of Caribbean culture through food, dance, and music as fundraisers for scholarships to assist Black students to attend recently desegregated schools in southern Ontario.

[3] Emancipation Day Parades began to celebrate the liberation of the enslaved throughout the Americas and were largely observed around the same time as the Calypso Carnivals.

The parades were marked as a Black victory over the British and operated as a military-style event, displaying military regalia, marching bands, and drum corps.

[35] Plans for the first Caribana began in February 1966, when a group from Toronto’s West Indian community came together in an abandoned firehall on Bathurst Street and formed a celebration for Canada’s centennial.

[36][37] This group consisted of ten individuals[35] with its board members mostly made up of expatriate-Caribbean nationals living in Canada.

[38] Charles Roach and Julius Alexander Isaac (the first Black judge of the Federal Court of Appeal) were among the community leaders who organized the first Caribana.

During this decade, the competing interests of the Metro police, city officials, and the corporate sponsors of Caribana threatened to overshadow the CCC's leadership.

[46] Following Puff Daddy's performance in 1997, many observers raised concerns regarding cultural retention and festival organizers' moral-cultural responsibility.

[47] At launch in Nathan Phillips Square, Premier Bob Rae calls the event a "beacon of hope" for all Canadians, as a symbol of racial harmony.

[48] With attendance down, the board chair blamed the federal and provincial tourism ministries for not funding their American advertising campaign.

[49] In 1997, the bandleaders threatened to boycott the parade if they were not paid for the year’s previous festival and provided with the necessary seed-money to fund production for 1997.

[55] In 2006, the City of Toronto government, unsatisfied by the CCC's financial audit report, invited the TMBA to apply for funding to operate and manage Caribana for 2006.

[citation needed] The name Caribana was invented by the organizers to capture the notions of Canada, the Caribbean, bacchanal and merrymaking.

In April 2010, a panel for the World Intellectual Property Organization (WIPO) ruled that Scotiabank, as the sponsors of the Caribana festival, did not have grounds for being awarded the domain name caribana.com from its current owners the Working Word Co-operative.

Economic studies estimate that the festival contributes approximately $400 million into Ontario's economy each year with the Federal Government being the largest beneficiary.