The circle certainly wasn’t broken on Tuesday night in Bridgeport, CT, where bluegrass upstart Billy Strings sat in with country legend Willie Nelson. The guest appearance came as part of Nelson’s traveling Outlaw Festival, which made a stop at Hartford HealthCare Amphitheater.

Strings and his bandmates Billy Failing (banjo), Royal Masat (bass), Jarrod Walker (mandolin), and Alex Hargreaves (fiddle) emerged from the wings to help The Red Headed Stranger wind down his set with the penultimate pairing of “I’ll Fly Away” and “Will The Circle Be Unbroken?”. Strings has been a regular participant in the show-closing singalong for several of the past few Outlaw Fest stops, but this time his whole band got to join in sans instruments to provide backing vocals. The 89-year-old ringleader of the tour, which also featured sets by Brittney Spencer and Larkin Poe on Tuesday, threw gasoline on Strings’ incendiary playing as he yelled over, “Play it, Billy!”

Prior to Willie’s headlining set, Billy turned in a 14-song performance of his own. Along with his four bandmates, Strings delivered a set that mined both their own catalog and their range of influences. Fan-favorite covers like “Slow Train”, “Ernest T. Grass”, and “Little Maggie” were mixed in beside classic originals including “This Old World”, “Away From The Mire”, “Long Forgotten Dream”, and others. The performance came to a climax as Strings and company strung together “Dust In A Baggie”, John Hartford‘s “With A Vamp In The Middle”, and “Wargasm”. The ever-growing live act was able to connect with a new audience that was drawn in by the festival’s illustrious host.

Check out a gallery of images from Tuesday’s Outlaw Festival stop courtesy of photographer David Gray, as well as a collection of fan-shot videos of Billy Strings and Willie Nelson.

Willie Nelson, Billy Strings – “Will The Circle Be Unbroken?” (Roy Acuff) – Outlaw Music Festival – 9/13/22

[Video: Matt Frazier]

Willie Nelson – “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” – Outlaw Music Festival – 9/13/22

[Video: Matt Frazier]

Willie Nelson – “Good Hearted Woman” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Willie Nelson – “Angel Flying Too Close To The Ground” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “Slow Train” (Leroy Drumm, Cal Freeman) – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “This Old World” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “Little Maggie” (Traditional) – Outlaw Music Festival – 9/13/22

Billy Strings – “Away From The Mire” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “Long Forgotten Dream” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “A Good Woman’s Love” (Cy Coben) – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “Summertime” (George Gershwin) – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “Dust In A Baggie” – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

Billy Strings – “With A Vamp In The Middle” (John Hartford) – Outlaw Music Festival – 9/13/22

[Video: Amy Karibian]

View Videos

Setlist: Billy Strings | Hartford HealthCare Amphitheater | Bridgeport, CT | 9/13/22

Set: Slow Train (Leroy Drumm, Cal Freeman), This Old World, Ernest T. Grass (Ronnie Bowman, Dan Tyminski) > Little Maggie (Traditional), Nothing’s Working, Whisper My Name (Ebo Walker), Away From The Mire, Long Forgotten Dream, A Good Woman’s Love (Cy Coben), Dusty Miller (Traditional), Summertime (George Gershwin), Dust In A Baggie > With A Vamp In The Middle (John Hartford) > Wargasm