Lindsey Webster had already shared a stage with Amy Helm and Donald Fagen and performed in front of David Bowie before her music career took off.

The smooth jazz singer grew up and still resides in Woodstock, New York, famously a mecca for artists. The city is or has been home to Bowie, Fagen, the members of The Band (including Levon Helm, whose famous Midnight Rambles were held at his eponymous studio in the town), jazz drummer Jack DeJohnette and many more. As the self-described “daughter of loving hippie parents,” per her website, Webster grew up soaking it all in.

“I’m a huge Steely Dan fan, huge Donald Fagen fan, and I always — because Donald lived in Woodstock, so I would see him around and always be so intrigued by him because here’s the guy who writes all these bizarre lyrics with the most beautiful and crazy music,” Webster said from her home office, about a week before her two-night, three-show stand at Jazz at the Oxford on Friday and Saturday.

The night she performed with Fagen was one of three times she performed at Levon Helm Studios with Amy Helm (sadly, she never made it to a Ramble before Levon’s death in 2012, she said).

“He actually ended up playing organ on a song of mine that night,” Webster said. “These are the things that happen in Woodstock. These huge stars just are around and they’re so low-key, most times you don’t know. We walk into a bar in Woodstock and Jack DeJohnette is sitting there at the bar.”

Or Bowie, who once showed up unannounced at a private event Webster performed and left before she had a chance to meet him. “I didn’t know at the time; I didn’t know that he was there until somebody came up and told me that David Bowie was there that night,” she said.

Webster has been able to count herself among the town’s “famous” population for at least the last few years, ever since her 2016 single “Fool Me Once” became the first vocal track to top Billboard’s Smooth Jazz chart since Sade’s “Soldier of Love” in 2010, and only the second overall since the chart started in 2005. She scored another No. 1 on that same chart the next year with “Were Do You Want to Go,” and was named Billboard’s Smooth Jazz Artist of the Year in 2016 and Contemporary Jazz Artist of the Year in 2017.

Singing has always been a part of Webster’s life — she remembered watching TV commercials for greatest-hits compilations and memorizing song snippets from Earth, Wind and Fire and others. But in elementary school, she picked up the cello and played the instrument for the next 12 years.

“Then I moved out of a school district that had music,” Webster said. “… When I lost my cello and my lessons — cellos are very expensive and so are the lessons, so it fell by the wayside; my parents couldn’t swing it. So I really think that’s when I started singing a lot more because I just had to have that musical outlet.”

Her music career took off after she met her songwriting partner, musical director and now husband, Keith Slattery, in 2009 at a karaoke bar in Woodstock. At the time, Webster haunted local open mic nights and karaoke bars and would sing hooks on her friends’ hip-hop tracks.

“When I first met Keith, his first question was, ‘Wow, you’re a great singer; what are you doing with yourself?’” Webster said. “And I really wasn’t doing much at that point. So he said, ‘Oh, well, I think we could probably get some gigs together just singing at country clubs and bars and stuff,’ and I was like, ‘Yeah, man, that sounds great.’ So that’s what we first started working on together, was just getting that material, and then as we became better friends … he was like, ‘We should try writing together.’”

Since then, Webster’s three studio albums have focused on the couple’s songwriting partnership. The upcoming “Love Inside,” her second album for Shanachie Records, drops Friday, making her Bend dates de facto album release parties.

“It seems that with each album Keith and I write, we become more efficient and better at it,” Webster said. “… The interesting thing about ‘Love Inside’ though is that we didn’t play any of this stuff before we recorded it. I don’t know if it’s a blessing or not because all these songs are really hard to do live. I swear, these are the hardest songs to sing live that I’ve ever written.”