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

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.

Daily, 4 Day and Weekend tickets are available. 
Kids 12 and under are FREE when accompanied by a paid adult.
No exchanges, refunds or Re-entry. Rain or Shine.
** Artists Subject to Change


  • 3:30pm Gates Open
  • 3:45pm – 4:45pm – Stay Tuned!
  • 5:15pm – 6:15pm – Stay Tuned!
  • 6:45pm – 8:00pm – The Soul Rebels
  • 8:30pm – 10:00pm – Boyz II Men




  • 1:15pm Gates Open
  • 1:30pm – 2:45pm – REH / CJH Youth Jazz Band
  • 3:15pm – 4:15pm – Stay Tuned!
  • 4:45pm – 6:00pm – Stay Tuned!
  • 6:30pm – 8:00pm – Yonder Mountain String Band
  • 8:30pm – 10:00pm – Alison Krauss

** Schedule and Artists subject to change

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