As it nears a half-century of festivals, Clearwater Jazz Holiday has set the table for its big party happening this fall.
Today, the nonprofit Clearwater Jazz Holiday Foundation shared the 2026 lineup which includes almost two dozen acts like trumpeter Chris Botti, Prince collaborator Sheila E., Cuban-American multi-instrumentalist and composer Arturo Sandoval, sibling roots-rock band Larkin Poe, and genre-twisting Americana band The Wood Brothers. Dumpstaphunk is set to play the music of Sly & the Family Stone on the festival’s final night, too.
Organizers for Clearwater Jazz Holiday—set for Oct. 15-18 at Coachman Park—have really leaned into their habit of giving each day its own musical personality. In 2026 those themes are cool jazz, rhythm, blues and brass, and roots and funk.
Other headliners in the 47th Clearwater Jazz Holiday lineup are Big Sam’s Funky Nation, and the smooth jazz trio of Kim Waters, Jeff Kashiwa and Steve Oliver.
“We aspire to make the festival feel curated from the moment you walk into the park. It’s not just a series of unrelated concerts, and that’s always back of mind as we program,” Clearwater Jazz Holiday Executive Director told Creative Loafing Tampa Bay. “I think this year is really unique in that way.”
Continuing to lean back into its roots as a free music festival, Clearwater Jazz Holiday will once again offer no-cover viewing opportunities from Coachman Park’s “Sunset Bluff.”
Festival goers can also access two ticketed general admission areas where blankets and lawn chairs are welcome. Additional reserved seating and VIP areas will also be available.
Organizers have also started to get into a groove programming two additional stages on the Coachman Park plaza and pier. Welcoming homegrown talent, those stages will host performances by Ronnie Dee & the Superstars, O Som Do Jazz, Carl Fischer’s Sunshine City Brass, Hammond wizard Shawn Brown, and many more.
Tampa jazz band ARConnection, led by pianist Pablo Arencibia and drummer Dave Rudolph, will also play a “Fires Of Forever” Chick Corea tribute, honoring the late jazz great who called Clearwater home (Corea died in 2021 at the age of 79, and that home recently went on the market).
Saxophonist Peter Carney, who will join ARConnection for the set, told CL that the group, which includes bassist Mauricio J. Rodriguez, has been working on the show for more than a year, adding that the show will include some of Corea’s biggest hits alongside new stuff from ARConnection that showcases the composer’s influence on the band.
“Pablo, Dave, Mauricio and myself have all contributed different elements to this group that make for an exciting tribute to Chick’s legacy,” Carney wrote in a text message. “Chick’s music is beyond category, starting with Miles Davis or Stan Getz to later playing with Michael Brecker and Christian McBride, Chick has been a centerpiece to jazz history.”
Admission to Clearwater Jazz Holiday set for Thursday-Sunday, Oct. 15-18 at Coachman Park in Clearwater includes no-cover options, but tickets that start at $39.
This is a developing post.
See the full 2026 Clearwater Jazz Holiday lineup below.
Thursday, Oct. 15: Cool Jazz
- Chris Botti
- Kim Waters, Jeff Kashiwa & Steve Oliver
- The Reinhardt/George Group ft. Barry Greene
- Tomkats Jazz Orchestra ft. Scotty Wright & Tony Castellano
Friday, Oct. 16: Feel the Rhythm
- Sheila E. & The E-Train
- Arturo Sandoval
- Ronnie Dee & The Superstars
- Latin Jazz Knights
- “Fires of Forever” An ARConnection Tribute to Chick Corea ft. Pete Carney
- EMIT Presents: O Som Do Jazz Brazilian Grooves
Saturday, Oct. 17: Blues & Brass
- Larkin Poe
- Big Sam’s Funky Nation
- Carl Fischer’s Sunshine City Brass
- Young Lions Alumni Jazz Blues Collective ft. Alex Malkovich, James Wall & Friends
- Shawn Brown
- Julie Black & Her Band
Sunday, Oct. 19: Roots & Funk
- The Wood Brothers
- Dumpsta Plays Sly: Dumpstaphunk Performs the Music of The Legendary Sly & The Family Stone
- Norside Organ Trio
- CJH Youth Allstars hosted by Frank Williams, Michael Kernodle & Tyler Wertman
- Freeman Sound Presents: The CHILLTronic Lounge ft. DJ Mister T.
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This article appears in June 11 – 17, 2026.