Greensky Bluegrass

Greensky Bluegrass got its start after winning the 2006 Telluride Bluegrass Festival band contest. This year, the group is a headliner. (Courtesy photo)

Every summer for the past 46 years, thousands of festivarians and musicians descend upon our tiny corner of the state for the world-renowned Telluride Bluegrass Festival.

With each festival comes different firsts, anniversaries, goosebump moments and four days of music in seemingly every corner of the box canyon.

In 2006, a group of musicians came to Telluride hoping for an opening in the festival’s band contest. The band was Greensky Bluegrass, and low and behold, it won the coveted honor that year, and played the mainstage the following year.

Also in 2007, another musician who flocked to Telluride in hopes of being noticed was Gregory Alan Isakov. He was vying for the title of Telluride Troubadour, a contest amongst singer-songwriters. It was the only contest the now highly acclaimed artist ever entered. He took the honors that year and played the small mid-day set reserved for each year’s troubadour winner.

Flash forward to 2019, and both Isakov and Greensky are headling the festival; Isakov playing Thursday at 5:30 p.m. and Greensky closing down Friday night with a 10:30 p.m. set.

“This is the first time we’ve had two past winners on the lineup together,” said Brian Eyster, director of communications for Planet Bluegrass, which produces the festival. Other notables this year include Sam Bush’s triumphant return to the stage after surgery this spring, the festival’s first ever set of comedy and much more.

Festivities officially kick off in Mountain Village’s Sunset Plaza on Wednesday from 5-8 p.m. with the annual Firstgrass, featuring the Jon Stickley Trio and an only-in-Telluride supergroup comprised of Ben Kauffman and Adam Aijala of Yonder Mountain String Band, Andy Thorn of Leftover Salmon, and Steve “Mojo” Mougin of the Sam Bush Band.

The Fred Shellman Stage in Telluride Town Park will open up Thursday morning with Chris Thile playing a solo opening set to get festivarians in the proper bluegrass mood.

Other notables on Thursday include Peter Rowan’s Free Mexican Airforce with Los Texmaniacs, the Telluride House Band with Sam Bush, Bela Fleck Jerry Douglas, Edgar Meyer, Bryan Sutton and Stuart Duncan, and Jim James of My Morning Jacket fame.

“Peter is super invigorated by this collaboration,” Eyster said of Los Texmaniacs.

The House Band set will be the first time Bush plays after he underwent surgery this spring, which forced him to cancel several dates up until last week.

“It’s going to probably be emotional for him walking out there on stage with his buddies,” Eyster said.

And as for James’ set, it’s been at the top of the Planet Bluegrass wishlist for years.

“He’s just the consummate collaborator, which fits so well into the festival spirit,” Eyster said. James will bring a full band with him.

Friday in Town Park promises to be a day of reunions, prodigies and festival favorites.

Molly Tuttle was named the International Bluegrass Music Awards guitar Player of the Year in 2017 and 2018 (she was the first ever female recipient of the award). She makes her Telluride debut at 1:30 p.m. Friday.

“She’s a great writer and singer, too,” Eyster said. “She’s really getting the attention she deserves.”

At 3 p.m., Broke Mountain Bluegrass Band reunites. Festivarians may not remember the band, but should certainly know its members — Travis Book of the Infamous Stringdusters, Andy Thorn of Leftover Salmon, Anders Beck of Greensky, Jon Stickley (playing Firstgrass with his trio) and Robin Davis (known for his monster guitar playing out of Durango). The band played together in the early 2000s in Durango, where all the members used to reside before they parted ways to move onto their latest projects.

“It’s been a big deal,” Eyster said. “They almost reunited at the Palm a few years ago during a Greensky Nightgrass. And decided that if they were ever going to get back together, it would be in Telluride.”

Lake Street Dive, Tim O’Brien, and Bela Fleck and the Flecktones are must-sees on Friday night as well. Fleck will return to the stage to close out the day with Greensky.

Saturday morning kicks off with an hour of the band contest finals, and as Planet Bluegrass Vice President Steve Symanski points out, the contest winners now get a bit more than just bragging rights and a cash prize.

“They get to record an album at Town Hall in Boulder,” Symanzki said. “That way when they perform at the 2020 festival, they’ll have an EP to sell to fans.”

Saturday afternoon’s 3:30 p.m. Yonder Mountain String Band set marks the band’s 20th anniversary of playing in Telluride Town Park. The midday show always inspires Yonder fans to throw marshmallows throughout the crowd, which occurs at this set only.  

While the marshmallows are fun, they prove to be distracting for the band and sometimes dangerous when hurled up onto the stage. Eyster has a challenge for Yonder fans as they commemorate two decades of Yonder in Telluride.

“The spirit of the marshmallows is great, but let’s find a better way to uniquely mark their 20th anniversary,” Eyster said.

So dear festivarians, can you brainstorm another way to have fun without impeding the band’s performance? Only time will tell.

Saturday night will also feature a festival first with Trae Crowder, Drew Morgan and Corey Forrester doing a comedy set from 6:30-7:15 p.m. These comedians pride themselves on their hillbilly roots with Crowder being known as the “Liberal Redneck,” and questions assumptions about both rural rednecks and urban liberals through comedy.

The festival wraps up Sunday with a lineup of powerhouse woman and some equally talented men, including the Jerry Douglas Band, Punch Brothers, Kacey Musgraves and Brandi Carlile. There will be more on Sunday’s female lineup in Sunday’s Daily Planet.

Additionally, the festival programs four days of free events in Elks Park, just off Colorado Avenue by the courthouse, while each night several venues open up for more intimate Nightgrass shows. (The late night shows sold out through a lottery in April.)

Elks Park proves a great alternative to the hustle and bustle of Town Park, or is an option if you do not have a pass to the sold-out festival.

The Elks lineup includes a bevy of must-sees, including a live disc cutting demo with Jim James on Thursday at 2 p.m., happy hour with Lake Street Dive at 4:30 p.m. on Thursday and the only festival performance from Chatham County Line Friday at 12:30 p.m., among others.

For a full lineup and more information, visit