What do you do when your project is taking off and life throws you its best curveball of all?

This was the striking scenario confronting Anna Lombard and her ambitious, talented bandmates in Gypsy Tailwind in August 2009. Lombard had just learned that she was going to be a mother, and it floored her. Can’t really strum your six-string with one hand and change diapers with the other, much less hop on tour and squeeze the troubadour existence for all its juice.

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Anna Lombard of Gypsy Tailwind, seen with bandmate Dan Connor, says, "My role in the band has always been to put my own spin on Dan's songs." Courtesy photo

And, as the band got hot, kicking off the Nateva Music Festival in Oxford with the likes of The Flaming Lips, Lombard ate humble pie and reoriented her life around her new sacred responsibility.

What makes Lombard’s story all the more remarkable is that her zeal to write and perform only grew while she was watching from the sidelines. Now, as the dusty folk troupe launches into its most promising year to date, Lombard is in a position to focus on her old and new loves at once. GO caught up with Portland’s newest rock star-mom before GT’s big New Year’s Eve bash with Rustic Overtones at Port City Music Hall.

It’s been quite a ride for Gypsy Tailwind, a lot of momentum in a short time. How was the band able to create this connection to its audience?

You know, it’s really the audience who is responsible for making that connection, not necessarily the band … as a listener, you want to experience something that moves you, or some way you really connect with the music or the words. Much of our “momentum” can be attributed to people genuinely believing in and loving what we create, and then passing it on to other people.

Are you proud of the band’s third record, “Decades and Days”?

Absolutely. It was very cool to see the progression of the band’s sound while I was away. Amanda (Gervasi) really came at it from her own angle, which has always been an important part of what Gypsy Tailwind is about.

How did you meet Amanda? How did you know she would be the right fit for when you took a break from the band?

It’s funny, actually. I didn’t even meet Amanda until this past summer, when I ran into her at a restaurant and thought she looked familiar but I couldn’t quite place her. We laugh about that now. She is yet another great example of how Portland has produced many, many talented musicians. The band was so lucky to find her, and even more fortunate when she actually agreed to join the band.

You were there at the beginning. What about the band’s approach or goals has changed since the winter of 2007?

Well … that’s a really hard question to answer, since I was away focusing on my own music, my beautiful baby and being a mom. But in returning, it seems everyone has grown so much, and we will remain focused on what is necessary for the band to continue to evolve — songwriting and practicing. A lot.

In what ways does the music bear out its Maine roots?

We are all so influenced by projects that we’ve all been involved in and people we have been fortunate enough to work with — Jerks of Grass, Rustic Overtones, Sara Hallie Richardson, Zach Jones, Spencer Albee, Pete Kilpatrick, Jason Spooner, Tony Boffa — there are so many, I can’t even name them all. Maine is rich in beauty and simplicity. Similarly, our music is so. Earthy, honest, at times pastoral, and lends an organic, rootsy sound.

How has becoming a mother impacted your songwriting?

I’m always learning. Always, always learning. Being around Dan (Connor, guitar and vocals) and the whole Gypsy Tailwind project has taught me so much about songwriting … and being a mother gives me so much more substance to write about, lyrically, and so many more notes to feel and sing. My role in the band has always been to put my own spin on Dan’s songs, while maintaining the integrity of the music he writes.

That being said, being away from it all provided me with clarity and certainty of the role of music in my life — that it’s my keel in high seas, it’s my passion and it’s something that I hope I can do for the rest of my life, hopefully with my Gypsy bandmates.

What’s on tap for Gypsy Tailwind in 2011?

We will be back in the studio this spring to record our fourth album. We’ll spend the beginning of the year lining up shows for the spring with perhaps an East Coast run to expand our fan base and get some exposure outside of Maine, New Hampshire and Massachusetts. We have a lot of surprises, and a lot of Gypsy tricks up our sleeves. Just you wait.

Mike Olcott is a freelance writer who lives in Portland and Boston.

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