Unforgettable Musical Moments
Telluride Bluegrass Festival

Unforgettable Musical Moments

Unforgettable Musical Moments

Unforgettable Musical Moments

Pushing the boundaries of Bluegrass

In 2023, we’ll celebrate 50 years of not-just-bluegrass. If you’ve been to the fest, you know what we’re talking about. If you haven’t, then you might be surprised to hear some of the headlining acts we’ve had over the years don’t quite fit into the Bill Monroe traditional bluegrass box. As they say, the grass is always bluer on the other side.

The incorporation of “wildcards” into our musical expression is intentional, and we love to lean into it. It’s our way of dodging norms, keeping things fresh, and introducing new and different acts to our febrile Festivarians. We deliver doses of musical medicine via melodies, harmonies, and these exploratory, soundful surprises.

Here are some (not all) of our genre-bending highlights through the years, as well as some indelible artists we look back on fondly time after time.

Do you have a favorite we haven’t mention here? Send us a message and tell us who/ why!

1976, 1977, 1987, 1980, 1981, 1983, 1985, 1987, 1988, 1991, 1993, 1998

John Hartford

John Hartford & NewGrass Revival circa 1989

1979, 1980, 1981, 1982, 1984, 1996

Norman Blake

Spotted: Nancy & Norman

1982, 1999

Willie Nelson

1983, 1986, 1987, 1993

Doc Watson

1986, 1989, 1990, 2003, 2018

The Nitty Gritty Dirt Band


Rodney Crowell & Roseanne Cash

We are in search of photos! Got any? Send ‘em HERE!


Alison Krauss and Union Station

1989, 1990, 1991, 1992, 1994, 1996, 1998, 2001, 2003, 2005, 2007, 2010, 2012, 2014

Alison Krauss holds the record for the second most Grammy awards won by a female artist (a whopping 27). The number one spot belongs to Beyoncé who has 28 wins (we concede that she deserves that one).

Alison holds the 4th spot on this list if you broaden it to include the most Grammys won by any individual musical artist. Her group Union Station has won 14 Grammys, the 3rd most decorated band behind U2 and Foo Fighters.

We’ll let those statistics speak for themselves, yeah?

1990, 1991, 1995

James Taylor

Back in 1990, Telluride Bluegrass didn’t have capacity restrictions. James played his set to a mesmerized crowd of 13,000 people. It wasn’t “sold out,” because what is a sell out if you don’t have a limit on your capacity?

When he returned in 1991, thousands more tacked on that number. A crowd of 16,000 packed itself into the park, sacrificing their 

Makes sense the two largest revolved around this superstar. We settled on an 11,500 capacity in 1992 and haven’t exceeded it since.

James returned to the TBF spotlight again in 1995.

James Taylor & Queen of Telluride Emmylou Harris


Mary Chapin Carpenter

1990, 1991, 1992, 1993, 1995, 1997, 1998, 1999, 2001, 2003.


The Chicks

Winners of the 1990 band contest, this early variation of The Chicks (pre Natalie Maines) was hot off their formation in Dallas. It’s a long road from Texas to Telluride, but boy are we glad they made the trip.

Wish we saw more outfits like this nowadays…

1992, 2014, 2022

Drepung Loseling Monks

1993, 2001, 2004

John Hiatt

1995, 2004

Ani DiFranco


Johnny Cash

This one kinda speaks for itself, right?


John Prine

John was a great friend of the festival and performed in 1997, 2006, 2012, and 2016. We miss him dearly.

1997, 2004

Guy Clark

1987, 1991, 1997, 2004, 2012

Lyle Lovett


David Crosby

We are in search of photos! Got any? Send ‘em HERE!

2000, 2013

Jackson Browne

Got any photos from 2000? Send ‘em our way!

2000, 2002, 2006

Bonnie Raitt

2004, 2021

Mavis Staples


Barenaked Ladies

2006, 2011, 2021

The Decemberists


Neko Case


Counting Crows


The Avett Brothers


Arlo Guthrie


Ryan Adams

Remember when Ryan covered Taylor Swift’s 1989 in full? Or was that a fever dream? Either way, we’ve never been able to forget it.


David Byrne

We are in search of photos! Got any? Send ‘em HERE!

2010, 2014, 2017, 2019

Brandi Carlile

2010, 2011

Mumford and Sons

It was a chilly, foggy evening in Telluride when Mumford and Sons took the stage for the first time.


John Fogerty

Talented guitarist and core founder of Creedence Clearwater Revival, John Fogerty’s storytelling spans generations.


Steve Winwood

Photo Credit: Candace Horgan


Janelle Monáe

2015, 2019

Kacey Musgraves


Nora Jones


Sturgill Simpson


Billy Strings

For all those asking (you know who you are), we fondly remember Billy Strings’ first performance on the Main Stage in 2018. Hard for him to top this one, maybe that’s why he hasn’t come back since?


Gregory Alan Isakov

2007 troubadour winner


Jierks Dentley

We still can’t believe this happened.


Tenacious D

As it turns out, Festivarians have a lot more crossover with D fans than you’d imagine. Must be the overwhelming love for authentic songwriting and soft spot for saxabooms.