Montserrat’s De Bear has been crowned the 2026 Leeward Islands Calypso Monarch following an electrifying regional at the Anguilla Summer Festival on August 8.

Anguilla’s Queen Roxxy was named first runner-up and Antigua’s King Young Destroyer finished as second runner-up.

There were eight contestants representing Anguilla, British Virgin Islands, St Kitts, Nevis, Antigua, Monserrat, Sint Maarten and the US Virgins Islands.

Organisers congratulated all of the performers for representing their islands with pride and passion and contributing to what was described as an unforgettable calypso showdown.