Montserrat’s De Bear was crowned the 2026 Leeward Islands Calypso Monarch last night, defeating contenders from across the region during the competition in Anguilla.

De Bear captured the title following what organizers described as an electrifying showcase of regional calypso talent at the Anguilla Summer Festival.

Anguilla’s Queen Roxxy finished as first runner-up, while Antigua and Barbuda’s King Young Destroyer secured the second runner-up position.

Organizers congratulated the winners and all the calypsonians who represented their islands, saying the competition demonstrated that calypso remains strong and vibrant throughout the Leeward Islands.

The regional competition is expected to return in 2027.

Source: Antigua News Room De Bear Crowned Leeward Islands Calypso Monarch; Antigua’s Young Destroyer Places Third.