Music, Community & Life on the Road with Caleb Stine
Music has a way of bringing people together in unexpected places. During a recent visit to Cape May, Breaking the Barrier School of Music owner Nic D’Orsaneo had the opportunity to sit down with traveling musician Caleb Stine at the historic Chalfonte Hotel.
With more than 30 years of experience performing music, Caleb has built a life centered around creativity, community, family, and connecting with people through song. Before taking the stage on the Chalfonte porch, he shared some of his experiences as a traveling musician and the lessons he has learned along the way.
What has your experience been like performing while traveling?
Caleb: I’ve been lucky enough to perform music for well over 30 years at this point, and there have been so many experiences.
Overall, I would say one of the best things about music—especially playing an instrument like the guitar—is that it’s portable. It can always be with you, and through music, you’re constantly meeting new people.
I think performing music has allowed me to build a life around community and creativity. One example is right here at the Chalfonte Hotel, the oldest hotel in Cape May, New Jersey. The hotel has been around for more than 150 years and is even rumored to have ghosts haunting the cupola!
Through my drummer, I was fortunate enough to start playing music here on the porch during the summer. I’ve now been doing it for six years. Experiences and connections like these are some of the greatest parts of being a musician.
How do you stay organized and maintain a high-quality performance while you’re on the road?
Caleb: Analog life.
For me, the key has been simplifying things and keeping my focus on what I’m actually trying to do: bring music and art to people and spread love through a creative life.
That’s also part of our family mission. I have an incredible wife and two kids, and we’re all on the same page about the life we’re building.
In terms of actual tools, I think it’s much better to have a notebook. In fact, I have a couple of different notebooks. That’s what helps me stay organized.
Can you describe a time when something unexpected happened during a performance?
Caleb: Last week, I was in Charleston, West Virginia, playing a show. I was performing for two hours, and during my first set, I played all original songs.
These were people I had never met before, but they seemed to be along for the ride.
During my second set, I noticed some phones starting to come out. Then someone approached me and said, “Hello. We’re from Philadelphia, and we love your song ‘Almost Heaven, West Virginia.’”
I was wearing a cowboy hat and singing songs, so I don’t think they were asking the wrong guy!
So, I played John Denver’s “Take Me Home, Country Roads.”
Suddenly, the entire room came alive. The women working behind the bar were swinging each other around like they were at an old-fashioned square dance.
It’s those unexpected moments that can bring an entire room together.
How do you connect with different audiences and adapt your performance?
Caleb: If I had to describe it, especially when talking to musicians and young musicians, I would say that it’s not a head thing. It’s a heart thing.
Music is a beautiful and complex language. Of course, you’re going to spend time in your head learning particular skills and understanding your instrument.
But at the end of the day, music is a beautiful outpouring of something from your soul that you’re sharing with someone else.
I think it’s important to stay grounded in the tone and sound of the music you’re making and to enjoy that sound yourself. That’s something I often return to, and I think that’s how you continue performing and connecting with people.
What motivates you to continue traveling and performing, and what do you hope audiences take away from your music?
Caleb: Both of those things are always changing.
I’ve been making and performing my own original music, along with American classics, for more than 25 years. When I was younger, my motivation came from different places. I was trying to find my path in life, figure out who I was, understand what life and music meant to me, and learn how to make a living doing it.
Now, I have two young children, and my wife is also a musician. I feel like I’m at a stage in life where I’m incredibly blessed. We’ve been given this amazing life and family.
Now, I’m in a keep-going mindset. I just want to continue playing shows. When people ask me to perform, I’ll try my best to say yes.
I want to keep creating situations where everyone wins and keep music on a very human level. Because that’s what music is. Ultimately, I think that human connection is what’s going to save music—and save us.
Creativity and Community Go Hand in Hand
The conversation also turned to The Ramble, the Cape May music event that brought Caleb to the Chalfonte porch, and musician and community organizer Chris Gillin-Schwartz.
Caleb: Chris is an example of a beautiful musician who is really living out the role of a musician, in my mind. He brings together his own unique combination of creativity and community.
Music is deeply personal to him. He writes songs, plays multiple instruments, and is an incredible pedal steel player. At the same time, he is committed to bringing music to his community.
That’s what we need. We need more of that.
Music Is About Connection
Caleb’s experiences are a reminder that music is about much more than playing the right notes. It can introduce us to new people, take us to unexpected places, strengthen communities, and create moments of connection that stay with us long after the final song.
At Breaking the Barrier School of Music, we believe every musician has something meaningful to share. Whether a student is picking up an instrument for the first time or preparing to perform for an audience, we’re proud to create opportunities for musicians to grow in their skills, build confidence, express themselves, and experience the community that music can create.
As a school that’s a beat above the rest, Breaking the Barrier School of Music provides high-quality music education in a welcoming, family-centered environment for students of all ages, abilities, and experience levels. For more articles like these or information on this school, visit https://btbschoolofmusic.com
