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Jillian Dawn comes back to Boston — and ‘Boston’

The 24-year-old Mansfield native performs at City Winery on July 29

Singer-songwriter Jillian Dawn.Susie McKeon

In her song “Boston,” Jillian Dawn describes an emotional affair with a taken man, but in real life she has never been the other woman. Like the musicians that she grew up listening to — Taylor Swift, Carrie Underwood, and Sara Bareilles — the 24-year-old singer-songwriter from Mansfield can turn a fleeting fantasy into a story both vivid and believable.

Dawn is a pop singer, but her singles “Fear of Heights” and “For the Night” highlight the country influences that come from her move to Nashville. Dawn headed to Music City to integrate herself in its robust music scene after graduating from the University of Miami in 2021, but she hasn’t abandoned Boston.


After performing at Berklee College of Music in March and singing the national anthem before a Boston Celtics game at TD Garden in May, Dawn is returning to Boston this Saturday, July 29, for her Headline Tour. Dawn will perform at the City Winery’s Haymarket Lounge. She plans to perform some new, unreleased music along with the songs and singles she’s released over the past few years.

Dawn spoke to the Globe this week via Zoom.

Q. What did your music career look like in Boston before you moved to Nashville?

A. I was a busker at Faneuil Hall. So I would be out in the street with my guitar, my sound system, and my little cart. I would play for a couple hours just for tips. That was definitely a hustle. I was also playing a lot of bar gigs.

Q. How are you liking the Nashville music scene?

A. I’m more of a pop singer and writer, so being in a country music city is crazy. The hustle from all of the artists in this city really inspires me. It’s so community driven here. Everybody knows everybody, and it’s super supportive. Music is constantly going on. I’ll be going to shows about three times a week, and I mean at least. I know people that go every night.


Q. Are there any specific Nashville musicians who inspire you?

A. I’d say any female artist that’s doing the thing is someone I look up to in this town. Unfortunately, with country music and with music in general, women are underplayed. Even the people that aren’t super famous — the attempt is something to admire. I’m constantly inspired, and I’m always meeting new artists and new writers in Nashville that come up out of the woodwork and make me want to be better.

Q. The imagery in your song “Boston” is so vivid.

A. I always feel like I need to preface the song with: It’s not a real story. It didn’t happen. It’s my imagination. I was in Boston when I wrote it. I would love to have my Boston song be an anthem about loving the city, but it’s not.

I wrote it when I was going into my senior year of college. I met a guy who was really cute and fun, but he had a girlfriend. So my crazy, insane brain was like, “What would happen if we crossed all those lines and something happened between us,” and that’s what the story became. I literally barely spoke to the man. That’s just how my songwriting brain works sometimes; it just over-dramatizes everything. It makes for some decent stories.


I wrote that song, I kid you not, in 45 minutes to an hour. It just kind of poured out of me. But I’ve never been the other woman! I need to clarify that! Every time I’ve played it while performing, I have to ask the awkward question: Has anyone here ever been the other person in a relationship? And sometimes people are brave enough to raise their hands or say, “Yeah.” It’s a very interesting one to play live because people really like it, but then they’re like . . . this storyline is . . . what’s going on here?

Q. If you could write a song titled “Boston” now, what would you do with it?

A. I think that if I wrote the song now it would just be an ode to the city. It’s home, and I can always go back there. It changes but it doesn’t change too much, you know? Every time I get to come back, it just makes me want to live there. I feel like sometimes I’m two different people. I feel like I’m an artist, and I’m here in Nashville to chase this career. But then there’s a huge part of me that loves Boston, that says, “Oh, I want to go back!”

Q. What are you anticipating for your show at City Winery?

A. I performed at City Winery last year when I was opening for the Dales, so it’s kind of surreal that I’m having a headline show. This show is the first time I’ll be playing with an official band in Boston, and I’m just so excited to play songs that people have heard over the years. All of my friends from high school have all my music streamed, but they didn’t see me play at school. They don’t see me play in Nashville. So I’m really excited to show them what I’ve learned over the years. I’m excited to make that introduction as an artist in Boston.


Elena Giardina can be reached at