Maine Troubadour Dan Blakeslee Performs at The Listening Room

Kate Schimke, artist, musician and lead organizer of The Listening Room told the Sentinel that she opened the unique venue in January 2025, and it since has been called a hidden gem by patrons who have attended concerts there. "I've had an art studio called Prayers of Nature in Wilton for eight years and hosted dozens of house concerts in my backyard for years. The weather was always unpredictable and I didn't like sharing my home with so many folks. I was working on my own music, released an EP and wanted to get back into the community setting," explained Schimke. She is looking forward to having her 7th concert on Saturday, May 17, with Dan Blakeslee. "I have 60 musicians waiting to play here. Dan reached out to me and wanted to play here since he enjoys playing in small, intimate venues. He's a phenomenal artist and authentic storyteller. He's weird and quirky in the best way," Schimke added. The Keene Sentinel spoke with Maine singer-songwriter Dan Blakeslee at his home in Kennebunkport, Maine. With a music career spanning 31 years and an art career to match, there was a lot of ground to cover. Victoria Chertok: Hi Dan, it's great to talk with you. Let's start at the beginning. You grew up in South Berwick, Maine, and live in Kennebunkport. How does living in Maine inform your art and music? Dan Blakeslee: Not just Maine but New England. There is so much magic to see here. I love all the seasons and I love how much nature there is to see and explore. Most of the songs and subject matter are true stories of my life: the good, the bad, the weird and everything in between. For example, one song, "My Lightning Valentino" has a great story. I wrote (it) in the White Mountains in Jackson at the Wildcat Inn. I overheard a story between two gentlemen at the bar after my show and one man said, "My lover gave me a white horse named Valentino as a gift." I was so knocked out by that I said, "Can you please tell me this story?" (and) they told me an epic tale. V.C.: You've been performing music for 31 years and making art for longer. You say you're grateful for every part of the journey – even the bumps in the road and said your parents were really supportive of your artistic path. D.B.: I got really lucky. My parents told me when I was a little kid, you do whatever you want to do that makes you the most happy and we will be behind you the whole way. I feel blessed everyday… My mother is an artist and my father is a musician. I grew up in a home where my dad, David Blakeslee, was and still is a professional jazz musician. My older brother introduced me to hip-hop and breakdancing early on so I'm a break dancer, and my younger brother introduced me to punk-rock and I was like, "Wow, I'm a musical mutt." V.C.: How did they support your artistic journey? D.B.: They jumped in and got me art lessons from a neighbor when I was in fifth grade. I was a hyper kid, a wild child, one thing they knew is Dan likes to draw and it makes him calm down. I'm so grateful that they kept that fire burning inside of me with art and music. The neighbor was Hal Kenyon, and he lived on a rural piece of property. I was drawing and having a blast with this fascinating friend of mine. V.C.: Where did those art lessons lead you? D.B.: I kept doing art through … high school. I came to a crossroads at around age 12 when I started to take piano lessons. In high school I started writing some songs and performing at school. I never felt piano was my strong instrument. I would go into my brother's room and grab his guitar. He taught me my first three chords. On the evening I was making the decision about college — art school or music school — I walked by an art gallery in Portsmouth and I was looking at this piece by Don Gorvett in the window — a very bold reduction wood cut of the old hotel Wentworth by the Sea. I said to myself, "I've got to go to art school!" It was a kind of divine intervention. V.C.: How cool is that! D.B.: Fifteen years later, I saw Don and told him, "You're the whole reason I went to art school," and he got really interested in what I was doing and was kind of a mentor from afar. I went to Maryland Institute College of Art in Baltimore. It was such a magical four years that will last forever in my mind. V.C.: It sounds like you really enjoyed art school. How did you start to take your music as seriously as your art? D.B.: My parents got me a guitar for my 18th birthday, so I brought it to school and didn't play it for the first year and a half. The workload was heavy and I needed something to let myself go, so I started playing guitar and writing songs. Towards my sophomore year, I started playing at open mics and cafés and then busking on the streets of Baltimore. Senior year I came out with my first ever album in 1994, "Dissolving Casteen." V.C.: Who were some of your early music influences? D.B.: Louis Armstrong, The Clash, REM — later I got into Johnny Cash and Bob Dylan and Joni Mitchell. She is an unreal performer, guitar player and songwriter. Her album, "Blue" came out the year I was born and I have it on CD, vinyl and tape. V.C.: I heard you started singing at a restaurant you worked at during the summers? D.B.: I worked at Barnacle Billy's lobster restaurant in Ogunquit, and I was a bus boy, dishwasher, prep cook, etc. I would sing as I was wiping down the tables and then other people asked me to come sing at their table. I would sing Elvis songs … In my seventh year there, my boss was very encouraging about my music. I gave him a copy of my first album, so when I came back that summer, he said "I can't hire you back," and I'm like, "What? I'm one of your best workers!" He knew that and said, "You're supposed to be out there playing music!" He told me to book my entire summer with as many shows as I could get and then I could work at the restaurant in between shows. He gave me the final push. V.C.: That's great! I heard he also helped you buy your first real guitar? D.B.: I was at a guitar shop and I played this guitar and it made me fall to my knees; it had the most beautiful sound. I told my boss, Court Tower, about it. It was way above my price range. He took out his wallet, gave me the money and said, "Take this money, take the day off and go buy that guitar and you can work it off." He had a way of treating all of his employees like gold. V.C.: Another incredible story of a helpful person in your life. D.B.: I filled up my schedule that summer. I was 21 years old, and I started busking on street corners in Ogunquit, Portland, Portsmouth and Boston, trying to get my music out there. Eventually I started doing music full time. My career is all music, my brain was so fried by doing so many art projects at college that I didn't want to draw for a while. The thing that got me back into drawing was making show posters for my shows. I was playing a show at Portsmouth at Smuttynose Brewery and they saw the posters I made and asked, "Do you want to make some beer labels?" I made seven or eight beer labels for their 16-ounce local brewed beer. I did them for a few breweries after that. V.C.: What happened next? D.B.: I was playing in New York City and Burlington, Vt. and going farther out to places in Virginia. Then I was at a café in Burlington, Vt. called Muddy Waters where I met the owner of The Alchemist brewery in Waterbury, Vt. (now in Stowe) and he said, "Would you want to make a beer label for us?" so I made the "Heady Topper" and "Focal Banger" beer labels for him. V.C.: Wow! How did you feel when you saw your art work on cans? D.B.: It blew my mind! I saw the "Heady Topper" truck go by with my art on the side of it and I thought, "This is nuts." It was surreal. V.C.: Let's switch gears and talk about your music career and your upcoming show at the Listening Room. D.B.: I was doing art projects by day and music by night. I figured out that I do a lot of artwork from November through March and then as spring comes I play more shows until October. I started out playing open mics sharing my songs and started booking gigs. V.C.: You have 11 albums of originals and play a few covers of Johnny Cash, Bob Dylan and The Clash. What are you looking forward to showing the audience at the Listening Room? D.B.: I love small intimate settings because I play so many different kinds of places, from Newport Folk Festival to tiny cafés. I'm really into rustic barns since I grew up on a farm. I'm really excited that it's a small listening crowd. V.C.: Tell me about your most recent album, "Road Hymns" (2023). D.B.: "Road Hymns," was recorded with a field recorder. It is solo acoustic. I've written all these songs that don't quite fit with my band and I was trying to figure out where to record it and so I did it like a travelogue. It's all recorded in different locations in New England that are sacred to me like on Monhegan Island in an old chapel in Maine; so many memorable times there. I recorded one in the subway in Somerville, Mass. since I was a subway musician for numerous years. I recorded one on my dad's sailboat and one in my mom's greenhouse. They all have different sounds: you can hear a river or ocean waves, etc. Throughout my career, my music is ever evolving — more electric sound, more explosive, more mellow. It took me years to find just the right room that fit what I'm doing. I finally found my groove. SHOW DETAILS Dan Blakeslee performs original music at the Listening Room, 33 Howard St., Wilton, on Saturday, May 17, at 7 p.m. Limited seating is available. Reserve a seat for $15 at prayersofnature.com/reserveaseat. For more information on the Listening Room, visit prayersofnature.com. For more information on Dan Blakeslee, visit danblakeslee.com.