Travel

Fall is the best time for Caribbean festivals

Swap fall foliage for these island festivals.

Festival season in the Caribbean may bring to mind lavish costumes and raucous parades for Carnival, but there’s more to explore, especially come fall. There are food fairs in Barbados and Jamaica, film fests in Cuba, and heritage celebrations from Dominica to St. Lucia. Whether you’re into arts and culture, music, gastronomy, scuba diving, or golf, the six Caribbean nations below offer vibrant fall festivals that celebrate the best of the West Indies.

Barbados

In mid-October, Barbados shows off its reputation as a Caribbean culinary jewel with the renowned Barbados Food and Rum Festival. Between October 19–22, you’ll immerse yourself in the Bajan way of life with eight different events across the island. The one you absolutely don’t want to miss? “Oistins Under the Stars,” a next-level, late-night ode to Oistin’s Friday Night Fish Fry hosted by award-winning local chef Creig Greenidge and Food Network star Chef Anne Burrell. There, be sure to sample the island’s legendary seafood, like fish cutter sandwiches and fresh grilled king fish. This year also marks the first De Bajan Fair, a family-friendly event with carnival rides, games, and, of course, food. Tickets can be purchased on the festival’s website, with prices for individual events starting at $20.

A little earlier in the month (October 12–15), you can mix your passions for jazz and golf at the Jazz Excursion and Golf Tournament, hosted by Barbadian-born saxophonist Elan Trotman. The event features R&B and jazz performers like Peabo Bryson and Regina Belle alongside a celebrity golf tournament across three sprawling courses. (You can tee off with the celebs if you book a hotel and ticket package, too.)

Jamaica

Aerial view of crowd at night at the Jamaica Food and Drink Festival

The party never stops in Jamaica, but Kingston is where you’ll want to be this fall. It’s home to the Jamaica Food and Drink Festival, which runs from October 25–29. There are six main events, including a jazz brunch, Pork Palooza pig roast, and a seafood and beer night, all of which feature local chefs and musicians who play while you dine. Keep an eye out for dishes that mesh international flavors with a taste of the island, like octopus spring rolls and scallops seasoned with scotch bonnet peppers.

And if you are looking for a nonstop, all-inclusive party, consider Frenchmen weekend, aka Hero’s Weekend, which commemorates Jamaica’s national heroes between October 14 and 16 in Ocho Rios. The weekend—a local fave—is made up of three events: a Rise Up breakfast party, the NiteCap pajama and lingerie party, and the Foreplay day party with food stations, a dance floor, and fireworks.

Cuba

Music and movies take center stage in fall and even into the winter in Cuba, starting in November with the month-long Habana Clásica, an international classical music festival that benefits the children’s ward of the Oncological Hospital of Havana this year. Yes, there are ticketed concerts, but keep an eye out for free pop-up performances in the capital’s plazas. And during the first two weeks of December, Cuba also hosts the LatAm equivalent of Cannes, the International Festival of New Latin American Cinema. Movie enthusiasts, directors, and actors (like past attendees Michael Moore and Benicio del Toro) flock from around the world to watch and judge films. The festival’s cinemas are open to the general public so you can snag tickets to the movies, which range from documentaries to short films.

Dominica

This tiny English-speaking island is known for its natural wonders (its hot springs, water falls, and beaches are all Travelers’ Choice Award winners) and its cuisine, which is rooted in Creole techniques with African and French influences. For more Creole culture beyond food, head to the island for the World Creole Music Festival, held October 27–29. It draws Afrocaribbean music lovers and artists from across the region and this year, headliners include soca singer Patrice Roberts and dancehall singer Popcaan.

For something a bit more unexpected, head to the island in mid-September for the Titiwi Festival, which celebrates the tiny, translucent titiwi fish. Throughout the hyper-local festival, you can sample titiwi fish in a variety of dishes, while zip-lining and playing beach football around the fishes’ home at the mouth of the Layou river, about 20 minutes from Dominica’s capital.

St. Martin

The French side of St. Martin is laidback and luxurious, making it the perfect place for a celebration of fine dining. The Festival de la Gastronomie runs from November 11–22, and attracts chefs from around the world, who attend to judge a food challenge based on a local ingredient. Last year, plantains were incorporated into every single dish and impressively, each competing restaurant came up with distinctly unique dishes, from plantain gnocchi from Lainez Bakery Pastry to plantain fritters from the famous lolo (shack) Rosemary’s. Visitors have the chance to take kids and adult cooking classes, led by guest chefs. You might even see familiar faces in the crowd, as actors Angela Bassett and Sidra Smith are regular attendees.

St. Lucia

Image: Management/Tripadvisor

St. Lucia is most often associated with its springtime jazz festival, but the fall is a great time to visit thanks to warm weather, low crowds, and lower plane fares. Another reason to visit, specifically for scuba divers, is St. Lucia Dive Fest, held at the Anse Chastanet Resort from September 23 to 30. At the dive fest, it’s all about water—with yacht charters, kayaking, and of course, scuba. You don’t have to be a pro to attend, and there are free beginner scuba diving courses to get you started.

If you’d rather stay on land, head to the island in October when St. Lucians gather to celebrate the Creole Heritage Festival. The festival’s blowout finale Jounen Kwéyòl (Creole Day) occurs on the final Sunday of the month and is the best time to immerse yourself in a colorful celebration of Creole culture. You’ll see St. Lucians draped in traditional red, yellow, and green madras print jackets, skirts, and dresses while they indulge in fried bakes, cocoa tea, callaloo, and green figs and saltfish, St. Lucia’s national dish. Expect live music and parades throughout the entire weekend.

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