Clearwater Jazz Holiday lineup: Chicago, Boyz II Men, Alison Krauss and more

Trombone Shorty and Orleans Avenue, Robert Randolph and the Family Band and more highlight the festival's 40th edition.
Chicago will be one of the headliners of the 2019 Clearwater Jazz Holiday in Coachman Park. Photo courtesy of Peter C. Pardini.
Chicago will be one of the headliners of the 2019 Clearwater Jazz Holiday in Coachman Park. Photo courtesy of Peter C. Pardini.
Published June 12

For its 40th incarnation, the Clearwater Jazz Holiday is going big. Rock and Roll Hall of Fame big. Dozens of Grammys big. Motownphilly big.

Chicago, Boyz II Men, Alison Krauss and Trombone Shorty and Orleans Avenue will headline this year's Clearwater Jazz Holiday, which celebrates the big 4-0 Oct. 17-20 at Coachman Park. Robert Randolph and the Family Band; Blood, Sweat and Tears; the Soul Rebels and Yonder Mountain String Band round out the initial lineup announced Wednesday, with more acts scheduled to be added in the coming weeks.

It's already an impressive bill. Rock and Roll Hall of Fame combo Chicago, which last played the Jazz Holiday in 2013, is a consistently big draw across the country. Boyz II Men were one of the biggest R&B acts of the '90s. Trombone Shorty is an electric performer and festival favorite. And bluegrass and country icon Krauss owns 27 Grammy Awards, third most of all time.

Here's the lineup by day so far:

Thursday, Oct. 17: Boyz II Men, Soul Rebels

Friday, Oct. 18: Trombone Shorty and Orleans Avenue, Robert Randolph and the Family Band

Saturday, Oct. 19: Chicago; Blood, Sweat and Tears

Sunday, Oct. 20: Alison Krauss, Yonder Mountain String Band

Among the additions yet to come: A performance celebrating the Jazz Holiday's 40th anniversary by a number of local and regional festival veterans. Details on that will be announced soon.

Pre-sale tickets are on sale now for $20 and up, $50 and up for reserved seating, and $175 and up for VIP. A general on-sale starts Friday.

Click here for the details on this year's Clearwater Jazz Holiday.

Contact Jay Cridlin at cridlin@tampabay.com or (727) 893-8336. Follow @JayCridlin.

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