New York City has Paul Simon, Jay-Z and The Velvet Underground. Detroit has Stevie Wonder, Diana Ross and Bob Seger. Vermont has Noah Kahan and songwriter extraordinaire Amy Allen.

If you don’t know where to look, it can be easy to gloss over Boston’s place in musical history.

“Boston is known for being kind of a culture of standoffishness,” said Alisa Amador, a bilingual singer-songwriter born in Cambridge. “Like, I’m not going to trust you right away, I’m not going to be friendly to you.’”

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Yet, Amador is one of thousands who call the city’s clubs, cafes and coffeehouses their home. Building on a rich past that includes Tufts University student Tracy Chapman, Berklee alum Aimee Mann and occasional Club Passim performer Bob Dylan, she and fellow songwriter Kemp Harris have spent decades honing their craft on stages and in classrooms — as a student and a teacher, respectively.

“My parents are Latin folk musicians [who are] still very much active and touring throughout Massachusetts, but also throughout the world,” said Amador, whose mother and father make up the duo Sol y Canto. “My childhood memories are very saturated with hiding in the velvet curtain while my parents were playing and watching them from the side, and playing in green rooms across America with my twin brother.”

Amador’s journey as a serious musician began at high school open mics, during which she played “stupid” love songs, as she called them, made up in between classes. Despite using a sub-par guitar at first — a gift from her father who wasn’t sure if she would stick with the instrument — her career skyrocketed in 2022, after her song “Milonga Accidental” became the first Spanish-language song to win NPR’s vaunted Tiny Desk Contest.

Written in the Argentine milonga folk rhythm, Amador said the song was written as an exploration of her cultural uncertainty, which took on a different meaning when she began feeling constant pressure to “make ends meet” off her art.

“This year, I’ve stepped back from touring just to recover,” Amador said. “Looking back on it, it’s kind of bittersweet, because I think the music industry is so toxic. … But I don’t actually have any regrets. I got to travel the world, and I still do. I just came back from playing a fan’s wedding in Mexico.”

Decades prior, Kemp Harris’ upbringing came with similar questions of identity. After emigrating from segregated North Carolina to Massachusetts, he began singing in church choirs as a boy, before making his solo — and secular — debut at a Cambridge coffee house in the ‘70s.

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“I went in and I played, and they passed a hat when you played,” Harris recalled. “And I think I made $28.”

Harris didn’t make performing music his full-time profession until much later in life, though he had 38 years’ worth of practice as an elementary school teacher. When he wasn’t plunking out Joni Mitchell songs for his students, he was experimenting with rock and funk, love songs and theater performances, and with his spoken word/beatnik/funk/poetry band, Neon Grandma.

That sense of artistic freedom abounds on his latest album, “The America Chronicles,” which serves up protest songs crossed with Marvin Gaye, Randy Newman and gospel and folk traditions.

“I think [living in Cambridge] allows me to write the kind of music that I write,” said Harris, who describes himself hitting the “trifecta” as a Black, gay, older man. “It allows me to express concerns that I see happening in our country. I just always felt a sense of acceptance, a sense of ‘you can be who you’re going to be and we’re going to support you in that.’”

Now that he’s retired, Harris plans on returning to the rock and soul that he gained local fame for performing, not content to “let the country dictate” what he plays. He sits on the board of Club Passim, where audiences can see him perform in December.

“I can’t do no more for America,” Harris joked. “But I still feel that calling.”

So does Amador. Next month, she, too, is playing Passim, a venue she performed in before her Tiny Desk victory — and a place where she used to nap during her parents’ Sol y Canto performances.

“I have this philosophy in one of my songs called “Together,” [where] I talk about how maybe the world is always going to be falling apart,” Amador said. “However, I think maybe it’s our purpose here in life as artists, but also just as humans, to be striving to put it back together again. And the only way that can happen is together.”

Guests

  • Alisa Amador, Cambridge singer/songwriter, winner of NPR’s Tiny Desk Contest in 2022
  • Kemp Harris, Boston-based singer, actor, activist and educator, board member of the Northeast Regional Folk Alliance and Club Passim