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The Monty Alexander Jazz Festival Celebrates 10 Years

Chesapeake Music brings renowned musicians to delight, engage and surprise today’s audiences, and educate, inspire and develop tomorrow’s.


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Don’t miss a swingin’ good time!

By Becca Newell

Monty Alexander
Photo by Joe Martinez

Celebrating its 10th anniversary, the Monty Alexander Jazz Festival returns to Easton this Labor Day weekend bigger and better than ever!

The energetic, ever-swingin’ festival features an exciting lineup, boasting some—if not the—best jazz musicians in the country, including guitarist/vocalist Allan Harris, pianist Matthew Whitaker, pianist Cyrus Chestnut, and the ever-phenomenal headliner, Monty Alexander.

The festival runs Friday, August 30th through Sunday, September 1st, with concerts at the Avalon Theatre in Easton, plus a Sunday morning brunch at Hunter’s Tavern, located at the Tidewater Inn.

Vocalist, guitarist, bandleader, and composer, Allan Harris kicks things off Friday at 8 p.m. with Nat King Cole at 100—a fitting tribute considering the Miami Herald referred to Harris as an artist blessed with “the warmth of Tony Bennett, the bite and rhythms sense of Sinatra, and the sly elegance of Nat ‘King’ Cole.”

“Jazz is a great expression of what we are,” Harris says, adding that he’s also a fan of the freedom within the genre. “Every night when we do a song, we do it differently. We keep the template of what it is, but try to stretch it a little bit.”

Randy Napoleon
Randy Napoleon
Photo by John Osler

Saturday’s program begins with a free community concert, starring jazz guitarists Randy Napoleon and Dan Wilson.

Rooted in jazz tradition, Napoleon is widely-known as a forward-thinking musician and one of the most sought-after guitarists in New York. In addition to leading his own trios and other small combos, Napoleon tours with legendary singer/pianist Freddy Cole. Guitarist George Benson calls him “sensational.”

Dan Wilson
Dan Wilson

From a young age, Wilson knew he wanted to pursue a career in music. Though his style is jazz-focused, it certainly draws influence from a wide variety of genres. He’s been touring nationally and internationally with three-time Grammy nominated jazz organ legend, Joey DeFrancesco. He describes the human connection between the performer and audience that’s created during a live show as “second to none.”

The duo’s performance, titled Guitars, Without Compromise, begins at 11 a.m.

Matthew Whitaker, who made his debut on the Festival stage last year at the Young Artist Showcase, returns—this time around in the Saturday matinee spot!

Blind since birth, Whitaker began performing at the age of three, when his grandfather gave him a small Yamaha keyboard.

By 15, he was named a Yamaha Artist, becoming the youngest musician to join this group of notable musicians. Hastily making a name for himself in the jazz world, the now 18-year-old was recently named one of seven rising stars for 2018 by USA Today network’s 201 Magazine.

Catch Whitaker in An Exciting Debut, An Eagerly Awaited Return at 2 p.m.

The Festival’s eponymous headliner takes the Avalon stage at 8 p.m. for what will undoubtedly be a lively celebration of his 10 years at the helm of the Monty Alexander Jazz Festival.

Considered one of the top five jazz pianists ever, Alexander’s musical expression combines elements of the blues, gospel, calypso, and reggae. He’s renowned for his vibrant personality, magnetic charisma, and breathtaking talent.

Tickets for Monty Alexander Celebrates the 10th Anniversary will sell out—and fast!

Unlike previous Festivals, this year’s Jazz Brunch will be held on a Sunday, which is great news for jazz enthusiasts as that means they won’t have to wait as long between Saturday’s showstopper and Sunday’s matinee for live music.

From 10 a.m. to noon, attendees can indulge in impeccably crafted brunch dishes while listening to the musical offerings of Wilson and Napoleon—the jazz guitarists featured at Saturday’s free community concert. Reservations via Hunter’s Tavern are required.

Closing out the weekend is pianist Cyrus Chestnut, performing Where Gospel Meets Jazz at 2 p.m. on Sunday, September 1st.

Born in Baltimore—his father the organist at his local church—the composer and producer says he’s always believed in the deep connection between jazz and God. His works unabashedly demonstrate this concept, seamlessly blending facets of jazz with elements of gospel, R&B, and classical genres.

Weekend passes for the Monty Alexander Jazz Festival, along with individual show tickets, are on sale now.

Over the last decade, the Festival has grown from a modest venture—comprising two performances by saxophonist Grace Kelly on its opening night and Alexander the following evening—to a three-day jazz extravaganza, featuring outstanding, first-class talent from across the nation.

“The response has been exceedingly enthusiastic,” says Festival Producer, Al Sikes.

Not only has the amount of shows presented increased, but the audience continues to expand rapidly, too. An unwavering optimist, Sikes admits with a hearty laugh, that he imagined bringing great jazz to the area would excite the community. Still, he’s been pleasantly surprised with the Festival’s ever-growing success.

“I’m just delighted at where we are,” he adds.


The Monty Alexander Jazz Festival is partially underwritten by the Maryland State Arts Council and the Talbot County Arts Council. Jazz on the Chesapeake is a program of Chesapeake Music. For more information or to purchase tickets, visit or call 410-819-0380.


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