Jamaica has reggae festivals, Trinidad revels in carnival and Barbados parties throughout Crop Over. In Anguilla, the biggest event is the Anguilla Summer Festival (ASF).

The three-week extravaganza celebrates its 50th anniversary from July 18 to August 11. Dee-Ann Kentish-Rogers, Anguilla’s minister of education and social development, heads the event’s organising committee.

In an interview with Observer Online, she said the government is going all out to make the golden anniversary, “an explosive and immersive experience.”

The ASF is a potpourri of leisure sport (high-speed boat races in the Poker Run), food (featured in Culinary Capital of The World) and music which can be enjoyed at Eyes Wide Shut, an all-white day fete.

Dee-Ann Kentish-Rogers

Kentish-Rogers has been formally involved in the ASF since 2017 when she entered and won the Miss Anguilla pageant. The event is her country’s biggest showpiece, with full participation from citizens and tourists.

She said it has evolved significantly over the years.

“The festival has an unusual etymology where it traverses religion, political upheaval and revolution, community groups and finally to its current destination under the ministry of social development. It has evolved from a simpler family bazaar to incorporating our national sport, boat racing, and it is currently a beautiful amalgamation of pageantry, fetes, boat racing, beach parties, soca raves and calypso,” Kentish-Rogers explained.

Located in the Leeward Islands, Anguilla is a British territory and has just over 16,000 citizens. Like most Caribbean countries, tourism is its biggest foreign exchange earner. The country, and that sector, were devastated by Hurricane Irma in 2017, but has made a major comeback in the last three years.

According to travelweekly.com, from January through March this year, Anguilla received 62,188 visitors, compared to similar periods in 2023 (50,884) and 49,952 in 2019.

Kentish-Rogers has served in different capacities for the ASF. Her current role is the most significant.

“My hope is to allow everyone to secure a piece of their hearts for Anguilla, as they come and enjoy a beyond-extraordinary experience,” she said.