Event· Carriacou· Windward Islands
Carriacou Regatta Festival
12° 29.0′ N · 61° 27.4′ W · approximate
Founded in 1965 and billed as the Caribbean's longest-running regatta: Carriacou-built wooden sloops race off Hillsborough over the first weekend of August, with donkey races, the greasy pole, street parties, music and island food ashore.
Practical
Coordinate is Hillsborough town centre (approx), the festival's traditional hub. Usually the first weekend of August (Noonsite). The 2026 edition ran July 31 to August 2, the first staged since Hurricane Beryl, with Republic Bank sponsoring the Large Deck Sloop class (NOW Grenada, July 2026). Hillsborough Bay can get rolly; a cruising family that stayed for the regatta anchored first off Hillsborough, then shifted to Tyrrel Bay and took buses back and forth. Expect a crowded Tyrrel Bay and busy ferries. Note that this is hurricane season, so keep an eye on the tropics and have a plan.
Best for
Watching traditional island sloops race
Season
Late July to early August (hurricane season)
Nearby
- Ade's Dream Supermarket (Hillsborough)Right here
- Carriacou CarnivalRight here
- Carriacou Maroon and String Band Music FestivalRight here
- Carriacou Museum (Hillsborough)Right here
- Carriacou Parang FestivalRight here
- Carriacou Taxis, Buses and Car HireRight here
- Hillsborough Fuel Station and LPG RefillsRight here
- Hillsborough Public MarketRight here