Grammy-winning trumpeter Chris Botti, Sheila E. and Larkin Poe headline the 47th Clearwater Jazz Holiday, four nights at Coachman Park starting Thursday, Oct. 15.

The festival returns to the park at 300 Cleveland St. with a "Back to Our Roots" format and a different theme each evening: Cool Jazz on Thursday, Feel the Rhythm on Friday, Blues & Brass on Saturday and Roots & Funk on Sunday.

"There's something truly special about live music on Clearwater's waterfront in October," Clearwater Jazz Holiday Foundation CEO Steve Weinberger told Beacon Media.

Each night opens with a free pre-party on two side stages: the VSPC Plaza Stage in the park's Lower Plaza and the Surfside Pier Party Stage on the Promenade Pier overlooking Clearwater Harbor. The music then moves to the Tampa Bay Times main stage for two main-stage sets per evening.

Night by night

Thursday, Oct. 15: Cool Jazz. Gates open at 4 p.m. Free side-stage acts include the Reinhardt/George Group featuring Barry Greene and the TomKats Jazz Orchestra with Scotty Wright and Tony Castellano. Kim Waters, Jeff Kashiwa and Steve Oliver play the main stage at 6 p.m., followed by a lighting ceremony at 7 p.m. and Chris Botti from 7:30 to 9:30 p.m.

Friday, Oct. 16: Feel the Rhythm. Gates open at 4 p.m. Side-stage performers include O Som Do Jazz, Latin Jazz Knights, Ronnie Dee & The Superstars and Fires of Forever, an ARConnection tribute to Chick Corea featuring Pete Carney. Arturo Sandoval takes the main stage at 7 p.m. Sheila E. & The E-Train close the night from 9 to 10:30 p.m.

Saturday, Oct. 17: Blues & Brass. Gates open at 3:30 p.m. Side-stage performers include Julie Black & Her Band, Carl Fischer & Sunshine City Brass, the Young Lions Alumni Jazz Blues Collective featuring Alex Malkovich, James Wall & Friends, and Shawn Brown. New Orleans brass outfit Big Sam's Funky Nation plays at 7 p.m. Sisters Rebecca and Megan Lovell of Larkin Poe headline from 9 to 10:30 p.m.

Sunday, Oct. 18: Roots & Funk. Gates open at 3:30 p.m. The CJH Youth All-Stars, hosted by Frank Williams, Michael Kernodle and Tyler Wertman with special guest Jose Valentino, open the VSPC Plaza Stage at 3:30 p.m. Dumpstaphunk performs "Dumpstaphunk Plays Sly" at 6 p.m. The Wood Brothers close the festival from 8 to 9:30 p.m.

Tickets and parking

Single-day tickets start at $49.92 in advance at ClearwaterJazz.com or by calling 727-461-5200. Options range from main lawn general admission to VIP reserved seating. Blankets and lawn chairs are permitted in the GA On The Green and Sunset Bluff areas.

Harbor Marine Parking, Lot 11, is the closest lot, charging $2 per hour until 6 p.m. with no charge after that, according to the Visit St. Pete/Clearwater event listing.

Community roots

The festival started decades ago as a series of concerts performed from the back of a flatbed truck. It now draws tens of thousands of visitors each year, according to the city of Clearwater. Past performers include Dizzy Gillespie, Dave Brubeck, Tito Puente and the Count Basie Orchestra.

The Clearwater Jazz Holiday Foundation, a 501(c)(3) nonprofit, also runs year-round youth programs. In 2025, the foundation delivered 29 presentations reaching more than 3,500 students and provided approximately $22,000 in scholarships and other special funding.

Upcoming Clearwater events