Singer Cassandra Carolan breaks the mold

It’s not often that dabbling in karaoke leads to a serious professional career, but Cassandra Carolan breaks the mold on a whole pile of assumptions.

She’s one of those people with a talent that seems so effortless that all the hard work and single-minded focus that goes into her success can easily be overlooked.

Cassandra recently performed at the Wednesday night jam at El Sombrero in Southington and she pretty much blew the roof off the place. I didn’t know what to expect when she took the stage, but musicians there told me to buckle up.

Can she ever sing. Cassandra’s powerful voice is one you don’t soon forget. She belts out rock, funk, soul and blues with a big voice and a big stage presence. Some of that may come from a confident talent, some from her younger days as a runway model in New York. Tall and lean, she has her own striking style.

Being a singer with a rock band was “the furthest from my mind,” she says of her later-in-life career path. These days she often does grandma duty during the day before transforming to her nighttime stage persona, rocking short-shorts and armed with a tambourine.

Besides the late start, Cassandra, a woman of color, is one of the few who sing classic rock. She took no formal lessons, but grew up singing in church, and in a musical family.

These days, she sings at venues all over the state with the band she formed, Cassandra and the Knighthawks. The group performed at the Concert on the Green series in Southington in June.

She also performs in a rock and blues duo, Relentless, and you can catch her show Nov. 18 at Witch Doctor Brewing Company in Southington.   

I asked her what it’s like as a Black woman playing the club circuit. Cassandra says it’s been rough pulling her own band together, but in terms of encountering racism, the hurdle has been “more sexist than racist.” Some business associates don’t take her seriously and “some men can’t take direction from a woman.”

She is definitely a woman with her own vision.

After raising a family, Cassandra began going to karaoke night at Gaetano’s Tavern on Main in Wallingford. She’d also been working as a classroom assistant in Wallingford schools. Looking to what she really wanted to do for her future, the music won out and she dove into the business decades later than most aspiring performers. 

“I’m a huge networker, I put myself out there,” she says, and those efforts have paid off in regular gigs at prominent venues.   

There’s more to come. She’s working up a Billie Holiday look and song list, an act in the vintage nightclub singer style. She’s talking about putting together a “summerfest” event for 2023, featuring some of the area’s best bands.

Breaking so many barriers in less than a decade seems quite remarkable but once you see Cassandra in action, it’s clear, she has what it takes to make things happen.

Reach Olivia L. Lawrence at


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