Carriacou Regatta festival started in 1965 as a mere boat racing event in Hillsborough Bay, Carriacou. Carriacou Regatta festival has now grown to become the biggest summer festival in the region. Held over the Emancipation weekend each year, it now includes a large number of Sporting and Cultural activity.
The Regatta Race events focus mainly on the locally built 'Workboats' with some twelve different classes of Boats ranging from 14 to 35 feet in length and participation from Tobago, Grenada, Canouan, Mayreau, Bequia(Grenadines), Petite Martinique, Antigua and Carriacou. Other aspects of the Festival includes: Donkey Racing, Greasy Pole, Miss Wet T-shirt, Miss Aquaval Queen Show with participation from Trinidad, Tobago, Grenada, Barbados, Canouan, Union Island and host Carriacou; Road Races and much more.