Montserrat is celebrating a major entertainment achievement after Keithroy “De Bear” Morson was crowned the 2026 Leeward Islands Calypso Monarch in Anguilla.

Morson captured the regional title on August 8, scoring 866 points to finish ahead of Anguilla’s Roxxy, who recorded 784 points, and Antigua’s Destroyer, who scored 746.

Following the victory, the Montserrat Government and Montserrat Arts Council organised a welcome-home celebration at John A. Osborne Airport, bringing together family, supporters, cultural practitioners and members of the wider community.

The achievement has placed Montserrat’s calypso tradition back in the regional spotlight and highlights the island’s continuing contribution to Caribbean music and cultural expression.

Morson’s victory is also a boost for Montserrat’s creative community, as the island continues to promote music, festivals and cultural activities as important parts of its identity and visitor appeal. Government policy has increasingly highlighted opportunities in the creative and “orange” economy.

The latest regional success gives Montserrat another high-profile cultural moment as entertainers and cultural organisations prepare for the island’s next major festival activities.