The Anguilla Summer Festival, which features the customary annual Carnival and Boat Racing activities, “came and went” – safely – and is now a part of Anguilla’s cultural history. Anguilla Summer Festival 2025 spanned the course of two weeks, beginning on Friday, July 25th and ending on Sunday, August 10th.
The pages of The Anguillian featured earlier events in its last edition prior to our Festival-week break. We now present commentary on other selected events of interest.
The Peter Perkins Boat Race at Sandy Ground took place on Sunday, July 27th. In the B-class small boats category, first place was taken by the “Upsetter”. In second place was “Kedro Pride”. Coming in third was “F5 Tornado”, while the “Hurricane came in fourth. The “Robb” ended up in 5th place.
In the A-class big boats category, first place was taken by “Justice”. Coming in at second was “Light & Peace”, and in third was “Satellite”. The “Real Deal” took fourth, while “Speed and Comfort” trailed in fifth.
The Miss Talented Teen Pageant was staged on the night of Thursday, July 31st. Ms. Ailyn Tavarez Sanchez was crowned as the 2025/2026 Ms. Talented Teen. She won Best Talent, Best Evening Wear, and Best Interview, garnering a total of 784 points. In the first runner-up position was Ms. Tajayne N. Summer Rogers, who won Best Inspirational Speech and was named Ms. Congeniality. In second runner-up position was Ms. Ayana Carty.
On the night of Sunday, August 3rd, the Adrian T. Hazell Primary School won the Princes and Princess Competition for the third consecutive year. Keandre Proctor and Ca’Miyah Hughes stole the spotlight from the other competing primary schools with a total of 464 points. They captured Best Talent Display. R’hayne Benjamin Richardson and Jean-Maire Halley of the Omololu International School placed first runner-up, and in the second runner-up slot was Pai’Jhon Marlin and Delicia Garraway of the Orealia Kelly Primary School.
The Talented Teen Show as well as the Prince and Princess Show were sponsored by the National Commercial Bank of Anguilla.
August 4th, culturally known as August Monday, saw three festival highlights – J’ouvert Morning, the Caribbean Beach Party at Sandy Ground, and the August Monday Boat Race. In the B-class category, first place was taken by the “Storm”, second place by “F5 Tornado”, and the “Hurricane” came in third. The “Upsetter” took fourth, while “Legal Rights” came in fifth.
In the A-class category, first place was taken by the “Sonic”. Coming in second was the “Wizard”. “Light & Peace” took third; the “Satellite” came in fourth, and in fifth was the “UFO”.
Tuesday night, August 5th, featured the much anticipated Miss Anguilla Pageant, traditionally known as the Carnival Queen Show. Ms. Jasmin Ruan from the Pond Ground was crowned Miss Anguilla 2025/2026 with a total of 1049 points. She was also named Miss Congeniality. The first runner-up position was taken by Ms. Ariel Bushay. She won Best Question and Answer. Ms. Jordia Hodge took the second runner-up position winning Best Introductory Speech, Best Swim Wear, Best National Wear, Best Talent, and Best Evening Wear. The other two contestants were Xaria Rouse and Thalia Hinds.
The major sponsor of the Miss Anguilla Pageant was the National Commercial Bank of Anguilla.
On Wednesday night, August 6th, the Landsome Bowl Cultural Center saw an array of performances as ten local calypsonians vied for the Senior Calypso Monarch crown. The winner was Roxanne “Roxxy” Webster, with 478 points, plucking the crown away from the defending ten-year champion, Anthony “Dr Splinter” Bryan. In the first runner-up position was Singing Vero, with a total of 454 points, and in the second runner-up position was Queen B with 449 points.
The Senior Calypso Monarch Competition was sponsored by ANGLEC and Motorworld. The grand prize – a 2025 GAC Emzoom GS3 was won by “Queen Roxxy”.
August Thursday, August 7th, featured two events – “Eyes Wide Shut” and the popular August Thursday Boat Races at Meads Bay. In the B-class category, first place was taken by the “Upsetter”, second was “Legal Rights”, third “De Storm”, fourth “Kedro Pride”; and fifth “Dark Shadows”.
In the A-class category, first place was taken by the “Sonic”. Second was “Light & Peace”, third “Satellite”, fourth Speed and Comfort”, and fifth “Real Deal”.
Friday, August 8th was the Parade of Troupes.
“Poker Run”, a fun-filled sporting event out at sea, took place on Saturday, August 9th. But the highlight for calypso contest lovers was the 28th Leeward Islands Calypso Monarch Competition held at the Landsome Bowl Cultural Centre.
A highly renowned annual Summer Festival feature did not disappoint again with 19-year-old Ge’Eve of Antigua and Barbuda claiming the prestigious title with 826 points. The 2024 champion Anthony ‘Dr Splinter’ Bryan surrendered his crown to Ge’Eve. The first runner-up was Queen Roxxy of Anguilla with 771 points, and second runner-up was Drewzy of St. Kitts with 761 points.
The final Summer Festival event was the Champion of Champions Boat races on Sunday 10th August. This year, in the B-class category first place position was taken by “F5 Tornado”, second place by the “Stay-Up”, third place by “Kedro Pride”, fourth place by the “Hurricane”, and fifth place by “Legal Rights”.
In the A-class big boats category, first place was taken by Light n Peace. “De Wizard” came in at second place and in third place was the “Satellite”. The “Real Deal” placed forth, while the UFO came in at fifth position.
The Summer Festival 2025 celebrations were characterized as being incident free, with sentiments regarding the safe and peaceful quality of the events echoed by the Royal Anguilla Police Force.
Chairman of the Anguilla Summer Festival is Fitzroy “Briggy” Tomlinson. He had high praises and admiration for the quality of the various festival shows, as well as the professionalism and excitement that surrounded the traditional boat racing sport.
