The Doobie Brothers perform Oct. 20 at the Clearwater Jazz Holiday.

CLEARWATER – What comes to mind when you think about the month of October?

It’s the month that traditionally ushers in cooler temperatures, bringing some relief from Florida’s seemingly endless summer heat. October also evokes images of pumpkin patches, jack-o’-lanterns and supermarket displays of Halloween treats.

In Pinellas, October also heralds the beginning of the outdoor music festival season. The festival season will kick off with one of the Tampa Bay area’s signature events: The four-day Clearwater Jazz Holiday will run Thursday through Sunday, Oct. 18-21, Coachman Park on the waterfront in downtown Clearwater.

Daily general admission tickets start at $20 in advance. Four-day and weekend tickets also are available. Children age 12 and younger will be admitted free but must be accompanied by a paying adult. For information, visit www.clearwaterjazz.com or call Clearwater Jazz Holiday office at 727-461-5200.

Presented by the HCI Group Inc., Ruth Eckerd Hall on the Road and the city of Clearwater, the festival will feature performances by headliners such as George Thorogood & The Destroyers, The Doobie Brothers and JJ Grey & Mofro. Morris Day & The Time and Sheila E will celebrate the music of Prince.

One of the longest-running and known events in the country, the Clearwater Jazz Holiday has presented in concert dozens of musical luminaries. Previous festival performers have included artists such as Woody Herman, Buddy Rich, Dizzy Gillespie, Herbie Mann, Dave Brubeck, Tito Puente, Stephan Grappelli, Stan Getz, the Count Basie Orchestra, Tony Bennett, Earth, Wind & Fire, Chicago, Bonnie Raitt, Trombone Shorty and many more. Over the years, the festival has embraced a diverse lineup covering a wide array of musical styles including straight ahead and smooth jazz, swing, blues, jam band, rock, folk, Americana, funk and Zydeco.

Now in its 39th year, this will mark the 13th year that the Clearwater Jazz Holiday will collaborate with Ruth Eckerd Hall to bring a diverse lineup of headline acts to Clearwater.

Presented in the 20-acre landscaped Coachman Park in downtown Clearwater overlooking Clearwater Harbor and the Memorial Causeway Bridge, the event promises four days and nights of some of the best live performances in the world. The visitor experience is complemented by the Clearwater area’s mild fall weather, miles of world-famous Gulf beaches, brilliant sunsets, nearby attractions, accommodations and dining to suit every taste and budget.

Following is a look at this year’s performance schedule:

Thursday, Oct. 18

  • Gates open at 3:30 p.m.
  • 3:45 to 4:45 p.m. – Adam Hawley
  • 5:15 to 6:15 p.m. – The Greg Billings Band
  • 6:45 to 8 p.m. – Mindi Abair & The Boneshakers
  • 8:30 to 10 p.m. – George Thorogood and The Destroyers

Friday, Oct. 19

  • Gates open at 4 p.m.
  • 4:30 to 5:30 p.m. – Betty Fox Brass Band
  • 6 to 7:15 p.m. – Danny Kusz
  • 7:45 to 9:15 p.m. – Sheila E.
  • 9:45 to 11 p.m. – Morris Day and The Time
  • 10:30 p.m. to 1:30 a.m. – Clearwater Jazz Holiday Official After Party at Capitol Theatre

Saturday, Oct. 20

  • Gates open at 1:45 p.m.
  • 2:15 4:45 p.m. – Clearwater Jazz Collective featuring La Lucha, Thomas Carabasi, Jeremy Carter, Valerie Gillespie, John Lamb, Mark Moultrup, Nate Najar, LaRue Nickelson, Gumbi Ortiz, Jamie Perlow, James Suggs and Butch Thomas
  • 5:15 to 6:45 p.m. – The Lao Tizer Band featuring Chieli Minucci, Karen Briggs and Nelson Rangell
  • 7:15 to 8:45 p.m. – The Fabulous Thunderbirds featuring Kim Wilson
  • 9:15 to 10:45 p.m. – The Doobie Brothers
  • 10:45 p.m. – Fireworks display presented by HCA West Florida Pinellas County hospitals

Sunday, Oct. 21

  • Gates open at 1:15 p.m.
  • 1:30 to 2:30 p.m. – REH/CJH Youth Jazz Band
  • 3 to 4:15 p.m. – Marcus Miller
  • 4:45 to 6 p.m. – Karl Denson's Tiny Universe
  • 6:30 to 8 p.m. – The Devil Makes Three
  • 8:30 to 10 p.m. – JJ Grey & Mofro

The mission of the Clearwater Jazz Holiday Foundation is to be the leading proponent of jazz entertainment and education in Florida through the annual presentation of a world-class, live music festival. The Clearwater Jazz Holiday Foundation Inc. is a 501c3 organization that has been center-stage for numerous scholarship and educational activities to benefit the music students of the community.

Festival headliners

George Thorogood and The Destroyers

It was way back in 1977 that George Thorogood and The Destroyers released their self-titled and now-classic debut on Rounder.

That album would soon be certified gold. On the album, the band covered a number of blues hits, including John Lee Hooker’s “One Bourbon, One Scotch, One Beer.”

Over the course of 16 studio albums – including six gold and two platinum discs on Rounder, EMI and Capitol – the band would amass an unmatched catalog of hits that includes “Who Do You Love,” “I Drink Alone,” “One Bourbon, One Scotch, One Beer,” “Move It On Over” and their most famous anthem, “Bad to the Bone.”

It was powerhouse live performances that truly made GT&D legendary, from unforgettable appearances on SNL and Live Aid, to the opening slot on the Rolling Stones’ historic ’81 tour, to their own record-breaking 50/50 tour.

Their spot at the Clearwater Jazz Holiday promises to raise the bar and rock the park.

“We play for a different audience every night and that keeps it fresh,” Thorogood said in a press release provided by Rounder. “There are people who’ve never seen us before, and we have to impress them. There are fans that keep coming back, and we want to surprise them.”

With more than 40 years, 15 million albums sold and 8,000 live shows after it all began, the title “professional rock performer” still means something to the man and his music.

“This is my job,” Thorogood said. “I’ve always loved it, and I love it now more than ever.”

Sheila E.

With the release of “The Glamorous Life,” her 1984 debut album, Sheila’s career took off.

Since its debut, Sheila has continued to grow as an artist, performer, and public figure. Her music catalog illustrates that evolution, from “Romance 1600” in 1985 to “Icon,” her seventh album, released in 2013.

Each one of her albums offers a glimpse into a different era of the musician’s life as she weaves her heart and soul into the various styles and genres in which she excels. Because of her passion, Sheila’s music is just as powerful now as it was decades ago.

For decades, Sheila E. has successfully captivated crowds of all ages with her dynamic personality, talent and passion for her music. Sheila pours her heart and soul into each musical performance. With rhythm and soul flowing through her veins, she lets her inner beat take the reins, making for a one-of-a-kind experience at each show.

Morris Day and The Time

Prince tapped Morris Day to take the lead vocalist spot in The Time. The band released “The Time” in 1981. The debut album features songs such as “Get It Up,” “Cool” and “Girl.” The band followed up with the album “What Time Is It” in 1982.

In 1984, the release of “Ice Cream Castle” coincided with the Prince feature film “Purple Rain.” In the film, Day played the antagonist Morris, a role that helped establish his playboy stage persona. “Ice Cream Castle” featured the hit “Jungle Love” as well as “The Bird.”

After recording these albums, Day launched his solo career, releasing three discs, including “The Color of Success” in 1985, “Daydreaming” in 1987 and “Guaranteed” in 1992. Combined sales of Day’s solo work and The Time’s releases is in excess of 10 million units.

The Doobie Brothers

The Doobie Brothers have been delivering mind-blowing, roots-based, harmony-laden, guitar-driven rock and roll for over four decades, selling more than 48 million albums and winning four Grammy Awards.

“Southbound,” the band’s most recent album, was released in 2014 on Arista Nashville. “Southbound” features new recordings of the band’s biggest hits, with country music’s biggest stars including Blake Shelton, Zac Brown Band, Brad Paisley and Toby Keith.

Boasting one of the most loyal fan bases in music, the band continues to write and record new material and tour the world. Their No. 1 singles “Black Water” (1974) and “What a Fool Believes” (1979), both gold, lead a catalog of indelible songs that also includes “Listen to the Music,” “China Grove,” “Jesus Is Just All Right,” “Rockin’ Down the Highway,” “Long Train Runnin’,” “Take Me In Your Arms,” Takin’ it to the Streets,” “Minute by Minute,” “You Belong to Me,” “The Doctor” and more.

In all, the Doobies have tallied up five top 10 singles and 16 top 40 hits. Beginning with their multi-million-selling sophomore collection “Toulouse Street” in 1972, the Doobies have three multi-platinum, seven platinum and 14 gold albums. Their “Best of the Doobies” (1976) has sold more than 12 million copies – making it a rare “diamond record.”

JJ Grey & Mofro

Southern soul-rockers JJ Grey & Mofro will close out this year’s Clearwater Jazz Holiday, taking the stage Sunday, Oct. 21, 8:30 p.m.

The band's charismatic live performances have captivated audiences all over the world, delivering songs with compassion and a relentless honesty.

“Ol’ Glory,” JJ Grey's latest record, captures the fierceness and intimacy that defines his live performance. Personal, Southern-inspired narratives, along with a sound boasting an eclectic blend of blues, rock, gospel and gritty R&B, have become synonymous with JJ Grey and his band Mofro.

JJ Grey is a do-it-yourselfer who is committed to making music that’s full of integrity. From the days of playing greasy local juke joints to headlining major festivals around the world including Bonnaroo, Glastonbury, North Sea Festival and Fuji Rock, JJ Grey remains an unfettered, blissful performer who sings with a blue-collared spirit over the bone-deep grooves of his compositions.

More music on tap

Among the other musicians set to take the stage at this year’s festival is Pinellas favorite and former St. Petersburg resident Mindi Abair.

Abair will perform with the Boneshakers Thursday, Oct. 18, 6:45 p.m.

The saxophonist, vocalist and songwriter last performed at the Clearwater Jazz Holiday in 2015.

Abair is carrying on a family tradition in the music industry. Her paternal grandmother was an opera singer and her father was a saxophonist and B3 player with the soul group The Entertainers. It was after that group broke up that the Abair family settled in St. Petersburg with their 5-year-old daughter Mindi.

By that time, the aspiring musician had already taken up the piano.

When she was in fourth grade, Abair switched to the saxophone and participated in as many band programs as possible throughout her school years. After attending the University of North Florida for one year, Abair transferred to the Berklee College of Music in Boston, Massachusetts. She graduated magna cum laude with a degree in woodwind performance.

Abair has released seven solo albums and played on countless collaborations in the studio and live on stage. In addition to her acclaimed body of solo work that includes 10 No. 1 radio hits and close to half a million albums sold, Abair was the featured saxophonist on the 2011 and 2012 seasons of “American Idol.” She jammed with Paul Shaffer on the “Late Show with David Letterman” and joined rock legends Aerosmith for their 2012 summer tour. In 2014, Abair received a Grammy nomination in the Best Pop Instrumental Album category for “Summer Horns,” a No. 1 recording with her friends Dave Koz, Gerald Albright and Richard Elliot, featuring four of the most pre-eminent saxophonists in contemporary music.

More recently, Abair received a 2015 Grammy nomination for Best Contemporary Instrumental Album for her follow-up solo CD “Wild Heart.”

For over 30 years, The Fabulous Thunderbirds have been the quintessential American band.

The group’s distinctive and powerful sound, influenced by a diversity of musical styles, manifested itself into a unique musical hybrid via such barnburners as “Tuff Enuff” and “Wrap It Up.” Co-founder Kim Wilson, the sole original member, still spearheads the group as it evolves into its newest incarnation.

“We started as a straight blues band,” Wilson said in a biography provided by Severn Records. “We now incorporate a mixture of a lot of different styles. We’re an American music band and we’re much higher energy than we were before.”

In addition to Wilson, the current Thunderbirds line-up features Jay Moeller on drums, Johnny Moeller and Mike Keller on guitar, and Randy Bermudes on bass.

Multi-instrumentalist and producer Marcus Miller has played multiple musical styles throughout his career, performing jazz, R&B and rock. Beginning with 1983’s “Suddenly,” he has released about a dozen solo recordings.

“Laid Black,” his 2018 release on Blue Note Records, sees the bass great bring the influence of modern urban music to his trademark sound on this genre-defying album.

According to Blue Note, anyone who has listened to Miller’s music or experienced his concerts live knows that they are in for quite a treat. Miller’s powerful, jazz/funk bass playing is out in full force with the new album. He’s pushing boundaries and taking jazz to new levels. Miller, along with his incredible band of young musicians, will be sure to excite, challenge and transport audiences.

The Devil Makes Three features Pete Bernhard, Cooper McBean and Lucia Turino. The trio will perform Sunday, Oct. 21, 6:30 to 8 p.m.

The band has been playing stomping folk for nearly 15 years – long before it started trending. As early roots influence in America grows, audiences can count on them not to sanitize its source material, or purge the suffering or the deviance or the repentance, from the stories they sing.

“That’s what we think the best stuff is,” Bernhard said in a press release from Riot Act Media. “And it belongs there. To take it out is to destroy it.”

In 2016, the trio released “Redemption & Ruin” on New West Records to critical acclaim. The album is a thoughtfully curated collection of covers that pays tribute to its versatile genre’s staple players and the band's most penetrative influences. Divided into two sides, the subjects of “redemption” and “ruin” are explored through various songs written by blues, roots, and rock legends such as Tom Waits, Willie Nelson, Kris Kristofferson, Townes Van Zandt and more.

Clearwater Jazz Holiday Official After Party

The fun doesn’t end when the music ends at Coachman Park.

Ruth Eckerd Hall on the Road will present the Clearwater Jazz Holiday Official After Party Friday, Oct. 20, 10:30 p.m., at Capitol Theatre, 405 Cleveland St., Clearwater. Tickets start at $21 in advance and $26 the day of the show. Call 727-791-7400 or visit www.atthecap.com.

The party will be hosted by Allon Sams and will feature Minneapolis-based saxophonist Danny Kusz, two-time winner of Creative Loafing's Best of the Bay and blues artist Betty Fox and soul/R&B vocalist Alex Harris.