Anguilla's 50th Summer Festival: A Calendar of Island Celebrations

With great fanfare, Anguilla is preparing to host its annual Summer Festival for the 50th year in a row. Taking place from July 21 to August 11, 2024, locals and visitors are urged to start making their plans to attend this event as it is expected to draw record interest from locals and travellers, making its moniker (“The Family Reunion”) more apt than ever.

Encapsulating a week of cultural events, music and engaging activities, this hotly anticipated occasion honours the warm, welcoming, and spirited culture of Anguilla and immortalizes the country’s emancipation.

With Carnival events incorporated throughout the festival, there's always a lively moment, so be prepared to celebrate. From boat racing competitions, food fairs, pageantry, live entertainment, and plenty more, Anguilla’s Summer Festival is a contender for the title of The Caribbean’s best party. Read on for a rundown of all the festivities.

A Week to Remember 

J'ouvert Street Jam: Will be held on Monday, August 5th, with a J'ouvert Celebration (meaning daybreak or morning). Unique in its own way, J'ouvert in The Caribbean is superior, as the day concludes on an exquisite white sand beach, and the sounds of soca and calypso get everyone into a dancing mood.

Miss Anguilla Pageant: On Tuesday, August 6th, look forward to the Miss Anguilla Pageant. Proud Anguillian women will compete for the sash and crown, and the day will also honour previous Miss Anguilla winners. The pageant will be championed by The Honourable Dee Ann Kentish Rogers, Minister of Education and Culture and Miss Anguilla 2017. An interesting tidbit: In 2018, The Hon. Ms. Kentish Rogers became the first black woman to be crowned Miss Universe Great Britain.

Calypso Monarch Competition: Anticipate the Calypso Monarch Competition on Wednesday, August 7th, when Anguilla's legendary talents and performances take the stage. Taking place at Landsome Bowl Cultural Centre, located in The Valley, prepare for a friendly duel of flawless melodies that you can dance and sing along to. The Calypso Monarch event is eagerly awaited each year, drawing crowds excited to immerse themselves in the music and culture of the island. 

Eyes Wide Shut & Grand Parade of Troupes: On Thursday, August 8th, prepare for an unforgettable evening extending into the morning, featuring live performances. This year's theme, 'Enchanted,' promises a dream-like experience. The Grand Parade of Troupes will follow the next day, Friday, August 9th. This joyous parade guarantees a colourful day filled with vibrant costumes and dancing. 

Poker Run: Wrapping up on Saturday, August 10th, prepare for a high-stakes card game that stops at five of Anguilla’s most exquisite beaches. With Anguilla's hottest DJs, competitions, and local foods, the festival concludes on Sunday, August 11th with a “Champ of Champs” boat race. Boat racing, a beloved sport in Anguilla, provides the perfect conclusion to a wonderful week of celebration. Watch locally made sailboats battle it out and cheer on your favourite as they race past the finish line. 

This year's Anguilla Summer Festival is set to showcase the vibrant culture and passionate community of Anguilla. With a full week of activities to look forward to, this fun celebration brings together tourists and locals alike. For more information, head over to https://ivisitanguilla.com/. And also check out what is going on all summer in our Event Dates Calendar.