Twenty-five years of Mondays. Uptown Mondays, one of Kingston’s most enduring weekly entertainment events, celebrates its 25th anniversary on Monday, October 19, 2026, and the lineup matches the milestone.

Dancehall stars Bounty Killer and Gyptian are billed as live performers for the anniversary edition, with Latonyastyle handling hosting duties. The musical selection comes from a heavyweight sound system lineup: Stone Love, World Team, DJ Mental and Game Changaz, a cross-section of the sound system culture that sits at the heart of Jamaica’s music scene.

Presented by Magnum Tonic Wine, the anniversary staging takes place at 35A Constant Spring Road. For a weekly event to run for a quarter of a century, through every shift in dancehall’s sound and every change in Kingston’s nightlife, is its own kind of legacy. Uptown Mondays has been a proving ground and a meeting place: where selectors break records, where veterans pull up, and where the newest generation comes to be seen.

Twenty-five years in, the celebration is as much about the culture that keeps showing up as it is about the performers on the bill. If you are in Kingston on the 19th, this is where the city will be.

Source: Maria Jackson 27 Magazine