Jess Klein has a girlish sort of voice, and she giggles freely in conversation. But the New York native sounds far from girlish when she uncorks her vocal cords and puts a hearty gust of wind into the emotive lyrics of a song. Since emerging from the Boston music scene a few years back, she has attracted quite a bit of hype in the folk arena, winning the Telluride Troubadour Songwriting Contest and receiving several Boston Music Award nominations. Her four full-length albums with Rykodisc have earned serious praise, including both of her 2007 releases, “City Garden” and “Live at Mo Pitkin’s House of Satisfaction.” During her national and international tours, she has shared the stage with monster acts like 10,000 Maniacs, Richard Shindell and Jill Sobule. New York Daily News named the title track of her 2005 disc, “Strawberry Lover,” one of the “Top Ten Sexiest Songs of the Moment,” alongside 50 Cent’s “Candy Shop” and Destiny’s Child’s “Soldier.” Klein has been compared to lasting songwriters like Emmylou Harris and Joan Osbourne, but, vocally, she sounds more like Martha Wainwright, emitting innocence and intensity in equal doses. The Wire spoke to Klein a couple of days before Thanksgiving about her evolving musical career and her four upcoming shows in southern New Hampshire, including stops in Durham and Dover.

You started playing guitar and writing songs in your late teens while living in Kingston, Jamaica. What were you doing there?
I was just basically a kid on a study abroad program. I didn’t go with the intention of writing songs. I was just going because it seemed like an interesting place to be. But, I had just started learning how to play guitar, and when I was there, culturally, music seemed like a very daily, vital part of people’s lives, and I really just responded to that. I was taking in so much information. I’d never really been out of upstate New York too much. And, just to be somewhere that’s so surrounded by a musical language and people who just seemed to have music in their veins really moved me. It’s real interesting how powerful an effect a geographical place can have on you. I was recently in Ireland on tour—I just did a tour of Europe—and it’s sort of the same way there. It’s a culture where people really put a high value on connecting with each other through music, and on storytelling, and that’s pretty different than the mainstream culture here.

When you came back to the States, you independently released your first two albums. How did you come to be signed by Rykodisc in 2000?
I think their A&R guy came to see me, and he was impressed. He came to see me at a venue in western Massachusetts called the Iron Horse. And then everything started happening at a much larger level.

After your first release with Ryko, you went on a worldwide tour, playing in Japan and elsewhere. What was it like touring all over the world for the first time?
On the one hand, it felt really natural. I mean, what drew me to writing and performing in the first place was that it wasn’t something I had to think about too much, it just seemed right. And then, on the other hand, there are all these things that you have to deal with when people are paying attention to you, when it’s your job and people are working for you and getting paid on the basis of your work and everything. So, actually, what it forced me to do was really grow a lot as an artist and get more invested in what I was doing. It couldn’t really be just everything was on a whim anymore. I had to really commit to it, and I had to do a lot of growing up in order to do that, because it’s not all a party, there’s a lot of hard work involved. But, I realized that this is really worth the work to me, because it’s just so rewarding.

So, you’ve been to Jamaica, you’ve toured the world, you were recently in Ireland … How has all this traveling and experiencing different cultures continued to affect your music and help it evolve, if at all?
That’s a good question. One thing, I guess, is that everywhere I perform, no matter where I am—I mean, unless it’s a really awful night or something—there’s always some kind of connection made with an audience, no matter what language is spoken there or what the economics of the town are or what the culture is like. I always feel that I’ve learned something more about humanity every time I perform. You don’t necessarily have to speak the language of the song you’re listening to to understand it, in a way. It operates on an emotional level. I just feel like people are a lot more alike than they are different, and that’s something I keep learning, and that’s very heartening, because of the state of the world and the war and all that.

Has your approach to songwriting changed much since those early days as a teenager in Jamaica? 
Actually, I would say it’s gone back (laughs) to how I used to write. I started off writing, because no one was listening at first, I felt really uninhibited and I wrote from a really emotional place. And then, I think, the more people started to listen to me, I got a little bit shy about stuff. And now, I’m interested again in writing from a more emotional place, but doing it in a way that also includes being a better crafter of songs, putting it together in a better way.

On part of the new disc, you begin talking to the audience and describing this MySpace message you got from a marine sergeant stationed in Iraq. Can you repeat what that message was about?
Basically, he had been a fan of my music, and in the message, he told me that he had been listening to music on his iPod when four bombs exploded about 40 yards from him. At the time, he wasn’t aware of anything but the bombs going off. He was OK, but then, a couple of days later, he was looking at his iPod and noticed that it had stopped on a song of mine called “Bombs Are Falling.” So, the title of his message was “coincidence.” And so, we just started writing back and forth and learning a little bit about each other’s lives and experiences, and it just sort of illustrates to me the power of music, that it could bring together people that seemed to be in really different circumstances and different paths in life. When you express something as an artist, you don’t always know who it’s going to affect or how. It was a really powerful realization.

You have a lot of songs that seem quite personal in their content, songs about love and so forth. But, you also have songs like “Holy Land” and “Bombs Falling,” which seem to get at bigger and broader issues facing the world. Do you feel compelled to write songs about bigger issues that affect everyone?
I do, because I feel that there was a time when I didn’t feel obligated—I sort of felt like I had the luxury to not think too much about politics or the world around me and things like that. But, things seem to be in a really dire place right now, and I think it’s just become imperative to pay attention to those sorts of things. I think that that can be very hard to do, because if you start thinking about all the troubles in the world, it gets overwhelming. What I’ve tried to do in my writing and in my work is, first of all, just to write from my own personal perspective, because that’s the only one I can know with certainty. But, also, just to recognize that there’s some healing that happens when you express a feeling, even if it’s a feeling of anger or a feeling of frustration. When I sing those songs and an audience can relate to them, there’s some healing that goes on there. Bringing that, already, is some small step I can make to help things be a little bit better.

The four upcoming shows you have here in southern New Hampshire are mostly in smaller, more intimate venues. Do you enjoy playing shows in small venues where you are up close and personal with the audience?
Yeah, I do, and I used to hate it (laughs). I used to really be made so nervous by it. It’s one thing to get up on a big stage and you can’t see the audience and it’s like you’re in your own world. It’s another thing to really open yourself up to an audience in a setting where you can see people’s faces and they’re closer to you physically. I think there’s a lot of power in that, and I’ve come to really enjoy it. It’s something that is missing a little bit, maybe, from our mainstream musical culture. Especially around the holidays, I think people want to feel like they’re connecting with something and experiencing something genuine together, removed from the stress of shopping and cooking and all that stuff. So, I’m pretty psyched to do these shows at the end of November.

You can hear a lot of different styles when listening to your music. There’s traditional folk elements, there are some that are bluesier and some that are peppier. Who are some of your major musical influences these days?
Well, I listen a lot to old blues stuff, like ’60s Chicago blues, people like Buddy Guy, and I like to listen to Howlin’ Wolf a lot. And then, from there, I like anything that’s influenced by the blues. I mean, I still love listening to the Stones and Led Zeppelin and all that stuff, and also people like Bob Dylan. I love listening to anything that has a rootsy element to it. I’ve been listening a lot to Wilco, and I’ve just gotten into this really amazing Irish writer named Declan O’Rourke, and he’s just a brilliant writer.

On your latest blog entry, you talk about recently losing your baggage at the airport in Illinois. Does the traveling and gigging and touring wear on you after a while?
It does in some ways, but, you know, I still have this romantic idea about being on the road. So, most of the time, I’m able to shake it off or make something creative of it, even if it’s not always fun to be spending your days in airports and your nights in a hotel. But usually I can make something creative out of it anyway.

Part of that blog entry jumped out at me. You’re talking about a Patty Griffin song you were listening to, and you say, “Don’t sing til you know what you’re saying, then slay the demon with all you’ve got.” Is that sort of how you approach singing each time you play a show?
Yeah, a little bit. I mean, it’s definitely how I approach performing a new song. I wouldn’t perform any song until I really felt like it was maybe 95 percent done, because I don’t feel like … I don’t know, I don’t want to waste anyone’s time (laughs) listening to me say something when I don’t know what I’m saying. So, yeah, I do feel that way. I think that’s part of why I became a writer, because when you write, you have the luxury of taking your time with what you’re gonna say, as opposed to just whatever slips out (laughs).

Last question—You’ve got four full-length albums under your belt, and you’ve toured the world. What do you think is next for you? What does the future look like?
Well, I just started working on some new songs, and I actually have a lot more touring coming up for the next couple months. But, I live in New York right now, and I’m actually looking to move somewhere else. So, foremost on my mind is writing new stuff and maybe looking to move somewhere a little more rural. I don’t know about moving to New Hampshire (laughs), but somewhere where there’s more trees and less traffic.

Jess Klein will be at Lake Shore Farm Inn, 275 Jenness Pond Road, Northwood, 603-942-5921, on Thursday, Nov. 29 at 7 p.m., $10. She will be at Tranquilities Tea Room, 4 Franklin Plaza, Upper Courtyard, Dover, 603-742-7625, on Friday, Nov. 30 at 6 p.m., $27.50 (benefit for Breast Cancer Stories). She will be at Mill Pond Center for the Arts, 50 Newmarket Road, Durham, 603-868-8999, on Saturday, Dec. 1 at 7 p.m., $15-$18. She will be at The Lion Restaurant, 4 North Road, Deerfield, 603-463-7374, on Sunday, Dec. 2 at 6 p.m., $50 (dinner included). For more information, visit www.jessklein.com.