The festival’s newcomer contests have impressive alumni

In 2007, Gregory Alan Isakov was looking for a way to fund a trip to the Telluride Bluegrass Festival to enter the event’s songwriting competition, known as the Troubadour Contest. 

Like many up-and-comers, the Boulder-based indie folk artist, Isakov, had to get creative.

“I was sleeping in my truck all the time. My goal back then was to sell like 10 CDs, pay for gas and the campsite and then keep going,” Isakov said. 

What Isakov didn’t plan on was winning the competition and a short, but coveted, set on the festival’s main stage. 

“(The contest) is over a few days. I would see my name on the telephone pole, at the end of every day. I ended up winning this guitar and it was amazing and I got to play a little set, like a ‘tweener set, on the main stage. It was just so magical,” he said. 

Now in its 33rd year, the Troubadour Contest has given newcomers an opportunity to showcase their talent to one of the genre’s most storied festivals and its crowd. 

The festival also features an even longer-running band contest that helped another prominent Colorado act get its start.

In 2006, a year before Isakov won the Troubadour Contest, the members of Greensky Bluegrass were sleeping in their tour van on the side of the road, hoping for a break. 

Coming from playing a gig at The Eldo Brewery in Crested Butte the night before, the band had hoped someone would drop out of the band contest so they may have an opportunity to showcase their genre-bending style of bluegrass to a bigger audience.

Sure enough, another act cancelled, and the band made the most of their break — winning the whole thing.

“There was a level of surprise because there were some great, great musicians in that … That was a real high watermark of Greensky Bluegrass and what we have been able to achieve over the last 20 years,” Greensky guitarist and vocalist, Dave Bruzza, said. 

Bruzza, along with a few other members of the band, are now all based in Colorado after forming the group after meeting at an open mic night in Kalamazoo, Mich. 

Both Greensky Bluegrass and Isakov will be returning to the festival’s stages this year, albeit with a bit more comfort than their earliest visits, this time as headliners instead.

“It’s undeniable the feeling you have when you’re there…  It’s really humbling to know that after all those years that they keep asking us to come back and it’s really something we all look forward to,” Bruzza added.

While artists can’t just show up anymore and perform in the competitions — contestants are selected beforehand now — the festival remains a launchpad for early career musicians in the age of Live Nation, Ticketmaster and industry consolidation. 

“In Denver and in Boulder, a lot of small venues are gone. I feel bad for young musicians right now because there were so many places to play when we were coming up, and now that feels more rare… The Troubadour Contest alone is so cool. There are so many great songwriters now that are coming up and that are playing,” Isakov said.

For Bruzza and his bandmates, decades of touring big stages have allowed them to step into a more-established role in the scene. 

“We do make some jokes about the passage of time, so to speak… We’re pretty accessible. You know, we’re not so locked away from people, and I think we’re all the community-oriented type,” Bruzza joked. 

Telluride Bluegrass Festival takes over the scenic mountain town for its 53rd annual run June 18-21.