Deep Roots

09/01/2026

Our Tuesday evenin’ tunes will feature Billy Maines! Click the link below for more details 🎶

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BillyPaula Logan Maines
Backdraft Restaurant
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

Americana singer/songwriter Billy Maines grew up in the foothills of the Catskill Mountains in a village on the Hudson River near Woodstock, New York. He started taking guitar lessons at an early age and played in various rock bands during high school. While attending college at Cortland College in....

08/31/2026

Our Monday night live music will feature Alanna Mosley! Click the link below for more details 🎶

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Bar Fontaine Cleveland
Cotton House, Cleveland, a Tribute Portfolio Hotel
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

Alanna Mosley is a singer-songwriter from Carrollton, Mississippi. Her music—best described as Americana or roots—blurs genre lines, and her cover tune catalog spans decades. With guitar in hand, Mosley is an unstoppable jukebox of great music that invites the listener to keep humming along.At a...

08/29/2026

Our Saturday night live music features Robin Webb! Click the link below for details 🎶

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West End Grille
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

Pianist Robin Webb has performed as a classical and cocktail soloist, in addition to combo and collaborative work on all seven continents, including Antarctica. Cruise ships, global destination resorts, New York and European cabaret houses and clubs, theatres on Broadway, London’s West End and reg...

08/28/2026

It’s Fourth Friday with Deep Roots! 6 pm with Joe Austin at the Delta Arts Alliance Ellis Theatre…FREE! Start your weekend off with live LOCAL music😎👍🏻 Visit Cleveland Mississippi 🎼

08/28/2026

Our Friday night tunes will feature Charles E. Sullivan II! Click the link below for more details 🎶

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Bar Fontaine Cleveland
Cotton House, Cleveland, a Tribute Portfolio Hotel
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

Americana singer Charles Sullivan sings a variety of styles, from folk and bluegrass to straight-up country. With influences like bluegrass great Ralph Stanley, folk master John Prine, pure country kings Johnny Cash and Waylon Jennings, and even genre-fusing groups like the Grateful Dead, Sullivan b...

08/27/2026

Our Thursday night live music will feature Guitar Frenchie! Click the link below for details 🎶

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Bar Fontaine Cleveland
Cotton House, Cleveland, a Tribute Portfolio Hotel
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

This hot-shot southpaw guitarist from Nimes, France, funded his move to the States by selling his Gibson Les Paul guitar. He’s forged through a rough-and-tumble 20 years, from jamming with blues legends to playing for hire. “I grew up on all American music — Rock ’n’ Roll and Blues — but...

08/25/2026

Our Tuesday evenin’ tunes will feature Mississippi Marshall! Click the link below for details 🎶

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Backdraft Restaurant
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Real Delta Tours and Artistry

Mississippi Marshall is a singer/songwriter/guitarist raised right in the heart of the Mississippi Delta. Marshall’s original guitar stylings range from old style Delta Blues to in-your-face blues boogie. His original music reflects his life experiences and for over 30 years, he has toured the cou...

08/24/2026

Don’t let the rain keep you inside ☔️ Our Monday night live music will feature Michael ‘Cadillac’ Dennis! Click the link below for details 🎶

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Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Cotton House, Cleveland, a Tribute Portfolio Hotel
Bar Fontaine Cleveland
Real Delta Tours and Artistry

Born and raised in the Mississippi Delta, ‘Cadillac’ Dennis’ musical journey began with singing and playing drums with the church choir as a kid. While majoring in music at Mississippi Valley State University, he began dabbling with guitar and piano. This led to his playing in a number of Gosp...