Living the Dream at America’s Greatest Bluegrass Festival



Cal & Aly


6 Mar 2024

Reading Time

8 mins


I was a fresh-faced 24-year-old at my first Telluride Bluegrass Festival, in the summer of 2012. The high-country sun was hot, and the San Juan Mountains cradled me and several thousand music fans in a natural amphitheater under bluebird skies. I spent four days barefoot in the grass, buzzed on New Belgium beer, listening to barn-burning fiddle solos and beautiful songwriting. John Prine was on the bill that summer, and I got to see my hero live for the first time ever. In the afternoons, I wandered home to nap, leaving my windows open so I could still hear the music floating through the air. In the evenings, I carried a sleeping bag out to the field and lay underneath the stars until the last notes rang off the canyon walls. As that lyric of John’s says, “How lucky can one man get?”

It didn’t take me long to understand why people drove from every state in the union to come to what locals just call  “Bluegrass.” It’s the pinnacle festival of summer and a beloved tradition, going strong since 1973. I was new to Telluride– a North Carolina native who’d taken a full-time job as a social worker, moving sight unseen to this gorgeous and rugged little town. Not only did I arrive in both a car and a coat unsuited to the Rocky Mountains, but I survived my first winter barely seeing the sun, living in a basement apartment without a ski pass. Naturally, I welcomed the warm and impossibly green summer that finally arrived in June. 

I’d written a few songs and built a small following playing covers in local restaurants, but in those days, I didn’t dream of being a full-time musician. Telluride was an expensive place to live, and I had a stable, fulfilling job that paid the rent. When I walked past Elks Park and saw the songwriters performing in the Troubadour contest, I envied their courage. Every year, ten singer-songwriters are handpicked as finalists from thousands of submissions to compete for a coveted slot on the Main Stage, a custom Shanti guitar, and the title of Telluride Troubadour. I didn’t even consider it a possibility.

By the next summer, however, I was exhausted and burned out from my social work job, and I began to lean more on music to lighten up my life. Emmylou Harris played Bluegrass that year and I nudged my way up through the crowd to watch her set. That weekend, my best friend Emily Coleman and I busked on Telluride’s main drag, opening my guitar case for tips. I sang “Red Dirt Girl” and “If I Needed You” and secretly hoped Emmylou would walk by and hear us. She didn’t. 

In August of 2013, I signed up for a songwriting retreat that changed the course of my life. Not only did it inspire me to write more seriously, it plugged me into a kindred music community and revealed a path to becoming an artist that I’d never dreamed of before. I left glowing. 

I knew this was a call I had to answer. I had no road map–none of us do. But I knew I had to quit my job and leave my safety net in Telluride.

Before leaving, there was one last thing I had to do: I went to the Telluride Town Park stage to say a prayer. I sat on the edge of that ramshackle wooden stage, looked out at the mountains, and promised myself that the next time I walked out there, it would be to sing my own songs.

Illustration by Abigail Fox

The following years were filled with thousands of miles on the road, making my home in an RV in parking lots and on public lands across America. My then-husband, Rous, was my cheerful copilot and roadie. I sang for whoever would listen, and sold CDs with album covers I designed myself. One night, I played a gig in Galveston to three people. The bartender was so moved that he bought all my albums and gave us gas money. That spring, I signed with an incredible booking agent; I’ve never played to a three-person house since. From coffee shops to concert halls, from being completely unknown to landing in Billboard and Rolling Stone, I worked obsessively through the ups and downs to build my audience and my chops.

My career was taking off. But every year I entered my songs into the Telluride Bluegrass Troubadour Contest, and every year I was passed over. Still, I loved going to Bluegrass as a fan. In 2017, Rous and I rolled back into town to hear my favorite artist, Brandi Carlile. She sang a new, unreleased song–“The Mother”– which stopped me in my tracks in the middle of that grassy field at dusk. Through tears I watched her bring the audience to their knees with just an acoustic guitar and a perfect song. I ached to do what she did–to make it up there and be a part of it all.


By 2019, I’d almost given up on the Troubadour contest. I’d been rejected for five years running, watching my friends and peers make it in, but never me. My hopes were thin and my ego a little bruised. I thought it might take another decade to earn a spot on that Bluegrass stage, and I made my peace with that. Then, an email surprised me in the middle of May. I held my breath as I scanned the list: I was a Troubadour finalist.

I took nothing for granted on that hot June day. I stood side-stage in Elks Park, fine-tuning my guitar in a blue dress and well-worn cowboy boots. I knew I had an edge in the contest: I’d been up at altitude for a month, acclimating so that I could sing effortlessly at 9,000 feet. My friends and fans made up two-thirds of the audience. I’d gotten married at the courthouse across the street and written half of my songs in these mountains. This was my home court. I felt a little guilty for how hungry I was to win. I sang high and clear, told all my best stories, brought the audience to tears and got a standing ovation.

The next day, veteran Bluegrass emcee Edee Gail announced my name and I made good on my long-ago promise. Five years after whispering my prayer, I walked out on that stage as the Troubadour winner. The weather for such a monumental day was hilariously bad–40 degrees and snowing. The Rocky Mountains like to remind you that, even in the middle of summer, winter is waiting in the wings. My friends shivered in their down jackets, faithfully cheering me on. But I don’t remember feeling cold. I was levitating.

I plugged in my guitar and took a moment to look out on the mountains and the community that formed me: Telluride. The journey to that stage was hard and winding, full of doubt and wonder, and sweeter than I could have ever imagined. I had no idea that I would sign a record deal with John Prine’s label two years later, or that three years later I would sing with Emmylou at the Country Music Hall of Fame. I dreamed of meeting Brandi Carlile, but didn’t know it would happen by surprise, backstage at the Ryman Auditorium, or that she would be so kind and warm and I would be too nervous to tell her what she meant to me.  

I knew nothing of what would come after that day. I could only sense that the next chapter of my life was beginning. I whispered thanks, and raised my voice to sing.

About the author

EMILY SCOTT ROBINSON is an internationally touring artist signed to Oh Boy Records. She has four albums under her belt and her song “Let ‘Em Burn” from American Siren landed the #19 slot on NPR’s 100 Best Songs of 2021. In her time off the road, she loves to mountain bike, drink great coffee and visit family and friends.

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