Trombone Shorty, who plays Coachman Park in Clearwater, Florida on Oct. 18, 2025. Credit: Photo by Jason Ryan c/o Gasparilla Music Festival

Clearwater Jazz Holiday finally gets to start a new chapter in its nearly 50-year history this fall—and today music fans learned who’ll provide the soundtrack.

Trombone Shorty, Vulfpeck’s Cory Wong, Trampled by Turtles, and Tower of Power are among the headliners coming to downtown Clearwater in October, along with Lady Blackbird, St. Paul & the Broken Bones, The War and Treaty, plus Richard Elliot and Rick Braun’s RnR ensemble.

The bill for the festival—which takes place Thursday-Sunday, Oct. 16-19 on the green at downtown Clearwater’s Coachman Park—includes nearly two dozen national and local acts playing three stages stretching between the pier and the large green “Sunset Bluff” which will be accessible for just $5.

Tickets for Clearwater Jazz Holiday happening Thursday-Sunday, Oct. 16-19 at Coachman Park go on sale to the public on Friday, May 23 are start at $5. A presale for Clearwater Jazz Holiday supporters and mailing list subscribers started today at noon.

Making the blanket and lawn chair-friendly bluff accessible for such a low price is a throwback to the days when Clearwater Jazz Holiday was free-to-attend. That vibe is something organizers wanted to bring back last fall before back-to-back hurricanes changed plans.

As usual, tickets that give concert goers access to seating and VIP areas are also available. Main lawn general admission tickets start at $35.

Steve Weinberger, CEO of Clearwater Jazz Holiday, told Creative Loafing Tampa Bay that the park can handle approximately 6,000 people a day.

Clearwater Jazz Holiday 2025 daily lineup

Thursday Oct. 16