Last Updated on August 10, 2026, 1:24 PM AST by Anthony Morris
The result of the Leeward Islands Calypso Monarch 2026 has been announced. This year the title 2026 Leeward Islands Calypso Monarch was won by De Bear from Montserrat. The event took place during the Anguilla Summer Festival 2026.
The 1st runner up was secured by Queen Roxy who was representing the Anguilla and King Young Destroyer from Antigua secured the 2nd place in the competition. The competition took place on Saturday August 8, 2026 at the Landsome Bowl Cultural Centre.
The Anguilla Summer Festival organization made the announcement of the winners online on their social media handle. The organization shared that the competition night was full of electrifying performances and participants proudly represented their island culture and tradition in their performances.
The Organisation said, “The Leeward Islands Calypso Monarch Competition 2026 was nothing short of amazing and spectacular! The incredible talent from across the region was on full display, with every contender giving their all in an unforgettable Calypso showdown”.
During the 2026 Leeward Islands Calypso Monarch competition a total of eight Caribbean islands participated. The names of islands were: Anguilla, Antigua, St. Kitts. Nevis, Montserrat, Sint Maarten, US Virgin Islands and British Virgin Islands.
Further the organization also congratulated the winners and participants for representing their islands. The Anguilla Summer Festival stated, “A huge congratulations to our winners and to every Calypsonian who represented their island with pride, passion and exceptional talent”.
The Organisation also shared the result of the 2026 Bro. Lee Sr. Calypso Monarch competition. The title was won by Queen Roxy who secured a total of 828 points in the competition. The 1st runner-up place was secured by Singing Vero with 813 points, 2nd runner-up place was secured by Mighty Springer with 799 points and 3rd runner-up was secured by Queen B with 793 points.
Notably, at the 2026 Leeward Islands Calypso Monarch competition St. Kitts was represented by King Drewzy and Nevis island was represented by Empress Lyric.
Anthony Morris covers stories related to politics and regional developments. His in-depth reporting about governance and reforms makes him stand out in regional journalism, with a deep analysis of political trends and their impact on Caribbean communities.
