Deep Roots

05/30/2026

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

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Backdraft Restaurant
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet

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...

05/30/2026

05/29/2026

Our Friday night live music featuring Michael ‘Cadillac’ Dennis starts soon! Click the link below for details 🎶

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Staple Cleveland
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet
Cotton House, Cleveland, a Tribute Portfolio Hotel

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...

05/28/2026

The 2026 Cleveland, MS Farmers Market season starts this Saturday with live music from Mississippi Marshall & the Juke Daddys! See y’all there 🎶😎

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Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet

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...

05/28/2026

Our Thursday night live music will feature Delta Sun & Brisket! Click the link below for details 🎶

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Backdraft Restaurant
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet
Mike Slaton Chris Livingston

Mike “Delta Sun” Slaton and Chris “Brisket” Livingston are singer/songwriters from the birthplace of American Music, the great state of Mississippi. They have been performing for audiences around the Southeastern United States for over 25 years. Their original and cover songs are inspired by...

05/27/2026

Rescheduled from last Friday...join us THIS Saturday, May 30 on the Downtown Deck in Visit Cleveland Mississippi! Michael 'Cadillac' Dennis and the Big Time Rhythm & Blues band at 6 pm! Bring your chairs and your coolers and enjoy live LOCAL music!🎼🎸🎷🥁👇🏻😎

05/26/2026

Our Tuesday evenin’ tunes will feature the talented Alanna Mosley! Click the link below for details 🎶

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Backdraft Restaurant
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet

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...

05/25/2026

Our Memorial Day music will feature Billy Maines! 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
Bolivar Bullet
BillyPaula Logan Maines

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....

05/22/2026

Our Friday night tunes will feature the talented Delta String Band duo! Click the link below for details 🎶

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Charles E. Sullivan II Cody Ruth
Cotton House, Cleveland, a Tribute Portfolio Hotel
Staple Cleveland
Cleveland-Bolivar County Chamber of Commerce
Visit Cleveland Mississippi
Cleveland Main Street
Bolivar Bullet

Roots musicians Charles Sullivan and Cody Ruth are members of the Delta String Band, an Americana band based out of Greenville, Mississippi. Similar to what the band presents, Charles and Cody sing a variety of styles, from folk and bluegrass to straight-up country. With influences like bluegrass gr...