February

• Black History Month

March

• Canadian Reggae Music Awards

April

• Reel World Film Festival (featured Super Bob produced by Jamaican-born Devon Haughton and starring some of the most talented Jamaican actors living in Toronto)
• Harry Jerome Awards
• Angus Glen Caribbean Golf Tournament

June

• Metro International Caravan (usually has a Jamaican pavilion)

July

• Caribbean Day Festival (Main Street, Markham)
• Jamaica Day Celebration
• Canadian Urban Music Awards

August

• Caribana
• Jamaican Independence Celebrations at City Hall
• Harriet Tubman Track Meet

September

• Toronto International Film Festival(Jamaican movies such as Shottas and Dance Hall Queen have been featured)
• The REEL BLACK AWARDS , Sponsored by the Black Film and Video Network

November

• Simulcast of Red Stripe Superstake to Woodbine International Racecourse from Caymanas Park in Jamaica at Toronto's Woodbine racetrack. An opportunity to also enjoy Jamaican food and music.

December

• Jamaican Canadian Association, Traditional Jamaican Christmas