After more than two decades as a jazz guitarist, Sheryl Bailey still invokes the name of a player who first inspired her love of the genre, but who died when she was just two years old.

“I got into jazz when I was about 15. I heard Wes Montgomery on the radio. I just fell in love with that,” Bailey said.

“What’s amazing about him is that he transcends the genre on his instrument. You could play him for anybody who says they hate jazz. If you play them Wes, they say, ‘I like that guy.’”

When Bailey first started guitar at the age of 13, she had no intention of playing jazz.

“I came from a family of church organists. My mother, my grandmother and my great-grandmother were all professional musicians,” she said.

“We all had to play classical music and take piano when we were kids. I was the youngest. I loved rock music, and I thought that would be a great way to stand out from all the other musicians in the family.”

Although her specialty is playing and composing jazz, Bailey says she never really left rock behind.

“I rely on a lot of skills in many of the gigs I do, and I love blues and rock guitar playing.”

Originally from Pittsburgh, Bailey attended Boston’s prestigious Berklee College of Music, mostly to learn about jazz harmony. For the past 17 years, she has been on the Berklee faculty.

“I definitely was very trippy the first time I came here and realized some of the teachers and musicians that I learned so much from and admired were now going to be my colleagues,” she said.

“All those guys are retiring now, so I feel that I can carry on their tradition and share all the great stuff they shared with me, so that feels good.”

Among the things she imparts to her students are lessons from her childhood about how to approach the task at hand.

“It’s the same as it was when my grandmother was running out to do gigs. There are professional principles of developing musicianship, so you’re prepared to do anything you’re called on to do.

“Things like being prepared, being on time, even down to dressing appropriately. All these things are being professional, whether you’re a church organist, or a jazz guitarist, or a funk recording producer.”

Even with the current emphasis on marketing and self-promotion in a changing music scene, Bailey’s take is blunt.

“If you’re going to be a side person, it doesn’t matter what your Facebook page looks like. If they walk into the club and you can’t play, you’re not going to get a gig.”

After a post-college teaching stint in Baltimore, Bailey moved to New York City in 1998 to pursue a performing career, in addition to being a prolific tunesmith.

“I always wrote and invented songs since I was a kid. It’s actually very relaxing and lighthearted, as opposed to playing the guitar, which takes a lot of discipline and angst,” she said.

“Writing music is always an adventure for me, so I try to do a lot of it.”

Bailey had long harboured a dream of forming an organ trio to play in small, intimate jazz venues such as Bar 55 on Christopher Street in Greenwich Village.

“I had this idea of doing an organ trio that was obviously in the blues and soul tradition, but also encompassed modern harmony and sound.”

It started to come together when she met Canadian drummer Ian Froman, during a gig with tenor saxophonist George Garzone at the Cornelia Street Café, another popular Village spot.

“I’d known of Ian for a long time, but that was the first time we’d played together and got to know each other.”

Bailey doesn’t remember how she met organist Ron Oswanski, but he and his Hammond B3, along with Froman, soon emerged as the Sheryl Bailey Trio.

“I called him to do a show at the 55 Bar, and he came in and played my music so beautifully that there was no question that he was the guy to fill that role.”

For almost 15 years, the trio has been “part of the fabric” of Bar 55.

“It’s a great place to hear music and a great place to play music. There’s a wonderful crowd of regulars, and because it’s such an iconic place, we always meet people from all over the world there,” Bailey said.

“You never know what’s going to happen, who you’re going to see. We love it there.”

Besides performing regularly in the Big Apple, the three have toured extensively. When they come to Whitehorse for a Jazz on the Wing concert this week, they will mostly play Bailey compositions from their 2013 CD, A Meeting of Minds.

As trio leader, Bailey is firm about what she offers her audience.

“It’s got to be melodic and it’s got to groove. It has to have that drive of rhythm and time that people feel.”

Once again, she invokes her early inspiration.

“That’s something Wes Montgomery had. He was so melodic and he swung so hard. His sense of time and delivery was so powerful that it was a complete package, really.”

The Sheryl Bailey Trio will take the Yukon Arts Centre stage at 7:30 p.m. on Sunday, December 2. For more information, check www.jazzyukon.ca.