Top Caribbean October Events

There's more going on in the Caribbean in October than hurricane parties – although, those can be a lot of fun, too! Nevis and St. Lucia play host to a pair of excellent food festivals during the month of September, while Bermuda brings in top acts for one of the region's best music festivals. If you like sailing, or just want to party with some sailors, then don't miss Bonaire's legendary regatta. October may be in hurricane season, but that doesn't mean you can't have a good time! Here are my picks for the top events, festivals, concerts and more during the month of October...

  • 01 of 07

    Al Green, Patti LaBelle, Beyonce, UB40, Alicia Keys and many others have graced the stage of the Bermuda Music Festival over the past decade-plus. Performances are held at Bermuda's National Sports Center as well as other venues, including the Fairmont Southampton. The four-day festival is very popular, so get your tickets early!

    Much like Mardi Gras in New Orleans, most of Bermuda shuts down for this four-day festival, delighting not only in its headlining acts, but also in the parties and celebrations across the island that accompany it. 

  • 02 of 07

    Food lovers, rum connoisseurs, chefs and other gourmands will gather in St. Lucia on the last weekend of October for the St. Lucia Food and Rum Festival, which will feature lectures, cooking demonstrations, dinners, and a Rum Pavilion offering tastings of more than 40 rums from across the Caribbean. The four-day event takes place at Rodney Bay Village.

  • 03 of 07

    This long-running (and week-long) regatta features races close to the coasts of Bonaire and Klein Bonaire, making it easy to follow the events from the shore. The festival around the races includes many events for sports fans, including softball, beach volleyball, and even a dominoes tournament. And of course lots of partying, including a street Carnival. A great time even if you're not a yacht racer or fan. The r​ace begins at Coco Beach and includes a variety of sailing divisions, including Sunfishes, Optimists, Beach Cats, and more. 

  • 04 of 07

    Held at the end of October, the World Creole Music Festival is the highlight of sleepy Dominica's annual cultural calendar and includes a broad variety of creole music and performers, touching on genres like Cadence-lypso, Kompas, Zouk, Soukous, Bouyon, and even Louisiana Zydeco. The festival typically coincides with Dominica's independence celebration, meaning even more parties and fun for visitors.

    Continue to 5 of 7 below.
  • 05 of 07

    The devastation wrought by the Soufriere Hills volcano on Montserrat in the mid-1990s had at least one silver lining: the waters around the island lay untouched for many years, allowing local underwater life to flourish. Anglers can take advantage during the annual Montserrat Fishing Tournament, which includes prizes for the best catches of Kingfish, Wahoo, Tuna, and Mahi Mahi.

  • 06 of 07

    Like mancala, warri is a "pit and pebble" game developed in ancient Africa and brought to the new world by African slaves in the 19th century. The game is still played throughout the Eastern Caribbean, and Antigua -- which boasts of having the world's best warri players -- holds an annual National Warri Festival at its Cultural Center.

  • 07 of 07

    Quick Guide to Caribbean Weather and Travel in October

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    © Paul Kandarian

    For more information on booking your Caribbean travel to the Caribbean and figuring out your itinerary once you get there, check out our October Travel Guide in the Caribbean and our article on Hurricane Season in the Caribbean, which passes through October.