Featured Musician: Clare Maloney and The Great Adventure

This is part of our ongoing series on musicians who perform in The Berkshires.

Since early April, Clare Maloney and The Great Adventure have performed five times in The Berkshires at the Ostrich Room at The Apple Tree Inn and the Lion’s Den at Red Lion Inn. The band has three more upcoming shows scheduled, including this Friday, June 16, at Egremont Barn. They are led by the classically trained and incredibly talented Clare Maloney. I had a chance to catch up with Clare over Zoom this Friday to learn more about this new artist who is catching on fire in The Berkshires. Our conversation has been lightly edited for clarity.

With your five recent and three upcoming shows, it seems like the Berkshires have fallen in love with Clare Maloney and The Great Adventure. How do you feel about the reception that you and the band are getting here?

I fell in love with the Berkshires 20 years ago, so I’m very happy about it. The Berkshires is a really special place for me, and I got my formative musical training at Tanglewood, where I spent three summers. And to have played at Apple Tree Inn right across the street from Tanglewood is really special for me. So any excuse I have to come to the Berkshires, and I’m there. I’m really happy that it’s working out with the band and that there’s been a great community welcome for us. There are shows to be performed, and there are people who come in to sing and dance with us. I couldn’t be happier about that.

You released your first full album Daybreaker, with nine songs on it, in December. How are you feeling about how the album has been received?

Clare Maloney and The Great Adventure - Daybreaker LP

I feel pretty good about it. I didn’t know what to expect. It was the first record that I put out. And one thing that was really cool was that when we put the record out, I asked on our social media channels, “What’s your favorite song on the record?” Every single song got picked by somebody. So that was really special to me because it’s an eclectic record. There hopefully is something for everybody. We span a wide range of genres, so it was really cool to see that everybody had their own favorite. It’s cool to me that even in today’s day and age, when people barely even have time to listen to a full record, people are listening to the whole album, and I couldn’t ask for more than that. 

I’m particularly a fan of two songs on the album, Dorado and Dream within a Dream. Both songs put me in a great mood while driving through the beautiful Berkshires. Can you share anything about either of those songs? Just you know? Is there any story behind them at all?

Dorado is a song that I actually wrote during a really dark period during the third wave of COVID. It was winter when we thought things had just opened; then everything really shut down again in New York. So that was a dark time. I had been fiddling around with this melody for months, and then I went to my cousin’s wedding in Palm Springs, California. And we were joking that we were kind of like the hippies that are just trying to keep up with really classy people, you know? But all of the desert imagery and the party vibe came from that. 

I wanted to write a song that captured those moments that you never want to let go of – those moments that you wish you could just live inside forever, but you know you can’t. It’s like nostalgia and wanderlust – like reaching for that moment when you’re not in that moment. So for me, it was the song that I needed to hear in a dark time. It was like a ray of sunshine on a cloudy day. 

Dream Within a Dream is inspired by an Edgar Allan Poe poem of the same name. I wrote it in March or April of 2021. Things were still shut down for us, and Nate and I were in Cape Cod for the winter. It seemed as though everybody had gone to Florida, and we were just trying to get up in the morning. A friend of mine had posted that poem, and I had never seen it before and was really taken with it. The poem has a lot of imagery about sand and the shore and reckoning with the mystery of life. I went to sleep that night, and when I woke up the next morning, I had the melody in my head for the chorus. I basically took the Edgar Allan Poe poem and did a colloquial translation of it. Its phrasing is of an older English, and I kind of like that. It’s literally like as if I translated it into 21st-century English. I took a lot of his story. I put in some imagery of my own, but it kind of reminded me of classical composers when they set poetry to music. So I kind of set his poem to music and changed his words a little bit so that it felt more like my voice. 

I have to go read the poem now.

Yeah, and here is a fun fact: We released that song as a single before the album came out about a year ago last June. The next day, in the New York Times crossword puzzle, the clue was “A Dream Within a Dream Poet.” That was really cool.

I read that you overcame writer’s block to write over 100 songs in 2021 which led to the album. Can you tell us a little bit about that experience?

It wasn’t fun – I wouldn’t recommend it to anybody. I had writer’s block for 11 or 12 years. I realized that I just lost my own voice completely. And it was so bad that I couldn’t even write emails. I couldn’t write anything. I remember I had a term paper due in college, a 20-page term paper, and I went to the library every night at six o’clock and I just sat there and stared at my laptop for four months.

So I spent a lot of the last decade trying to work through that. The key to uncovering that was to change the voice in my head. That was a very critical voice that was keeping me from putting anything on the blank page. And that, unfortunately, took a long time. And when the pandemic hit, we continued to play a lot because we had a live stream series that Nate and I did every Monday night. So we were playing a lot, but we weren’t playing any original music because none really existed in its completed form. And when we went into that second winter, the winter of 2020 – 2021, I realized things really weren’t going to open, and we weren’t gonna have work. I just said to myself, if I don’t use this time to write, I’m really gonna regret it. So while we were living in Cape Cod for that winter, I just got up every morning and tried to write for six or seven hours, and I had the time to do it. I wrote a lot, and it was good because I needed the practice, and it allowed me to work on the craft in an artful way. So I’m grateful for that.

Does that mean that you might have enough material saved up somewhere to do that next album?

I don’t know. I like to think that everything goes on the compost pile. There are a lot of songs that kind of got morphed into something else. Or maybe I took the melody from this, or I took the chord progression from that, or I took the lyric from one thing and put it in another thing. So there are definitely a lot of seeds that have been planted. Some of the songs are crazy. Some of them are dumb, like kids’ songs. I could put together a kid’s album of silly, funny songs. One of them was called Never Feed Your Dog an Avocado. And it’s really catchy. But I wouldn’t put that on a rock’n’roll record. 

We have a handful of songs that feel like they could go on the next record. But I would really like to write more –  I kind of miss writing. There’s a season for everything you know, and right now, we’re playing a lot, which is fantastic. But I do miss getting up and going to my writing desk and spending hours there. So I hope that I have some time for that at some point in the summer.

I listened to your interview with Johnny Irion on WSBS radio about your summers here at Tanglewood, which you mentioned earlier. I’m certain our Berkshire audience would love to hear about your origin story and how you got to where you are today. So could you recount that a little bit deeper?

Absolutely. I went to the Boston University Tanglewood Institute (BUTI) summer program for high school students between my junior and senior high school. I had just started taking voice lessons, and I remember I sent in a cassette tape for the audition. And I couldn’t believe that I got accepted – it was kind of a fluke. I was gonna do some other summer thing that had nothing to do with music.  

Had you been singing up to that point?

I was very musical. I played clarinet, flute, and guitar. And I had been taking voice lessons for about a year, and I think my voice teacher had a pamphlet for the BUTI and said I should apply to this. I couldn’t believe I got in, and then when I got there, and I heard the quality of all the other singers, I really couldn’t believe that I got in. I was like, “Whoa, these people are amazing.” These 16 and 17-year-old kids are just incredible singers. Tanglewood really gets the cream of the crop for musicians and classical music. And it was so inspiring for me. You take all kinds of classes – music history, music theory, language for opera, diction, French, Italian. You take voice lessons. And then you have a season pass for the Boston Symphony, and you get to see a show every single night if you want. So that was like I was in heaven, and I definitely got bit by the bug pretty hard. I remember going back to high school and thinking, “I can’t take regular history; I have to take music history.” And so that really turned my ship; I was like, “Oh, I really have to do this – there’s no question about it.”

What path were you on before that? Did you have any inkling of what you wanted to do?

That summer, I was actually able to go do a chemistry internship. I liked science. I also liked writing.

So the STEM fields may have lost you to the music industry 😀

Yes, it’s been a long strange trip, as they say. And I ended up going to Boston University for opera. And what was really cool was half of my incoming class were people I knew from Tanglewood. It was amazing. So I already had a lot of friends there, and I knew the faculty, which was really special. And then, I ended up spending a couple of summers working at the Tanglewood Institute. I got to spend two more summers living in Lenox and getting to see the symphony every night, and that’s really a dream, a dream within a dream within a dream. 

I went to BU, where I studied opera, and I ended up moving to New York after I lived in Boston, and for many years I was a choral singer. I did a lot of oratorios and early music – that was kind of my niche – and contemporary music. And I ended up working a pretty full schedule. I sang at Carnegie Hall several times, Lincoln Center, National Sawdust, and everything in between, doing a lot of classical music. I was always trying to discern where I was really meant to go. I love classical music – I’m the biggest nerd you’ll ever meet, but it didn’t always feel like the right place for me. I did some young artists programs in opera, so I ended up singing in Europe for a couple of summers, but it just didn’t feel quite right. 

I decided to take a job singing in a wedding band. In school, we weren’t allowed to sing anything that wasn’t classical music, not even Broadway. For my first gig, I had to learn 100 songs. I had to figure out how to sing “I will survive,” “Respect,” “September, songs by Adele, and everything in between. I ended up working with that company for about six years. And that was my transition out of doing mostly classical and into doing more pop. And during that time, I started getting some work as a background singer for rock and roll. And that’s kind of how I found my way into the rock and roll scene. It was actually through the Grateful Dead community. Honestly, I think it’s really cool for me to come out of being a really serious classical musician, with attention to detail to the extreme, and finding myself in the Grateful Dead scene where mistakes are welcome – where improv is the name of the game. It was a really soft place for me to land. And I felt really welcome and really at home – it was really cool. As a little kid, I loved rock and roll. I grew up on ZZ Top and the Eagles and all that kind of stuff. And so it sort of felt like I had taken the really long way around to kind of come back to where I started from. I guess that’s the journey.

You mentioned a few artists that influenced you – can you tell us some others?

Paul Simon, Bruce Springsteen, Sheryl Crow, Bob Dylan, Joni Mitchell. During the pandemic, I obsessively read artists’ autobiographies, like 60 of them, anybody’s that I could get my hands on. I read Debbie Harry’s and Springsteen’s, which was like 600 pages. I was studying them, studying their careers, and taking their songs apart and trying to study their songs, too. When I was a teenager, I particularly loved singer-songwriters like Ani DiFranco and Martin Sexton, who has one of the greatest voices of our time. And both are incredible entertainers. I went through a huge Radiohead phase. They were very influential on me, and Talking Heads.

I’m a huge Talking Heads fan as well!

Somebody at Appletree Inn came up to me last time and said, “You really remind me of Tina (Weymouth) when you play the bass.” Wow, that’s awesome! I’ll take it! I listened to Talking Heads: 77 every day for my entire junior year of college. Bjork – I definitely listened to her a lot. Obviously, Grateful Dead. And Jefferson Airplane. I studied Grace Slick as a method actor would. I watched tons of interviews with her.

Who’s popping up on your playlist right now?

I’ve been listening to a lot of My Morning Jacket. I’m really excited about what they’ve done. I feel like they are going to be very influential on the next record because I feel like they have really emotive songs.

This coming Friday will be your first performance at Egremont Barn, which is one of our 12 featured venues, as is Apple Tree Inn, The Lion’s Den (and nine others). Have you been to a show at the Barn before?

I’ve been to a couple of shows at the barn. I’ve been both inside and outside. It’s really magical out there. I’m really looking forward to it. 

On the three shows that I’ve seen, you’ve had the same band consisting of Nate Debrine (guitar, vocals), Russ Gottlieb (electric banjo, bass), and Caleb Estey (drums, vocals). Is that the band you’ll have at Egremont Barn?

Yes, that is the band for the summer and hopefully beyond.

Do you have anything different planned for this show?

We might be playing a brand-new original song, which will be cool. It’s finished, but we need to rehearse it more. And probably a new cover that we’ve been working on that Nate and Russ are going to do, which will be really fun. I’m not going to give it away – it will be a total surprise. And we’re gonna have a special guest sit in with us at Egremont Barn – our friend Jackson Whalan, who’s going to sit in on a tune with us, so that’ll be cool.

Is there anything else that I did not ask that you would like to share with our readers?

Just that I love the Berkshires, and we hope your readers will come to the show. We’d love to meet you.


You can learn more about Clare Maloney and The Great Adventure at claremaloney.com. You can find her music on all major streaming platforms, including Spotify, Apple Music, Pandora, and YouTube. You can also follow her on Instagram and Facebook.

— Mark @ Music in the Berkshires

Subscribe to Music in the Berkshires e-Newsletter