On a scorching summer evening in Hershey, PA for the 27th stop on Willie’s annual Outlaw Music Festival tour, Bob Dylan walked on stage with quiet eminence—cloaked in black and topped with a white feathered hat, taking his seat at the piano toward the back of the stage. He did not greet the crowd, nor did the 84-year-old indulge in theatrics beyond the occasional head-nod in the direction of his bandmates. The stage lighting remained the same throughout his 75-minute set, as did the static camera on the projection screen.
As he always has done throughout his mythic career, he let the music do the talking. Surrounded by his quartet on all sides like a kingpin with his cronies, Dylan delivered a raw and alluring performance—spinning inventively bluesy renditions of tracks across his songbook mixed with a few covers.
In a commodified musical landscape that deifies dead idols—the Hendrixes, Morrisons, and Joplins to the Cobains and Buckleys—what happens when one of the greats goes the distance? How does this relic of a particular era continue as he outlives his peers, his generation, and the very ethos into which his groundbreaking art was born? Though 60 years have passed since Bob Dylan went electric, and 61 since Willie Nelson first played the Grand Ole Opry, the two legends aren’t finished writing their stories just yet.
On classics like the recently revived “Masters of War”, “All Along the Watchtower”, and “Desolation Row”, Dylan’s gravelly voice and clacking keys wound through the verses that scholars, songwriters, and philosophers have meticulously dissected for decades. Whenever he stood to wail on his harmonica, the crowd cheered and watched with mesmerized appreciation. To close, Dylan launched into “Highway 61 Revisited” and “Don’t Think Twice, It’s Alright” to the great delight of the audience before departing the stage shrouded in even greater mystery than when he appeared.
Bob Dylan — “Masters Of War” — 8/9/25
[Video: pwm112]
Related: Is Bob Dylan Recording A New Album?
After a hype video of sorts, Willie Nelson & Family took the stage as a giant American flag dropped down in the background. Rocking his classic braids and headband, Nelson rolled on into his perennial opener, “Whiskey River”, as the crowd whooped and hollered. He meandered up and down the fretboard of his trusty guitar Trigger with surprising vigor for a 92-year-old on classic sing-alongs of his own as well as closely correlated covers like “On The Road Again” and “Mammas Don’t Let Your Babies Grow Up To Be Cowboys”, all met with thundering applause. Guitarist Waylon Payne enthusiastically helped out on vocals at times, but being the showman he is, Nelson largely commanded the crowd throughout the night.
Willie Nelson & Family — “Stay All Night (Stay A Little Longer)”, “Still Is Still Moving To Me” — 8/9/25
[Video: Ross Kardon]
A wise man once said, “He not busy being born is busy dying,” and these two troubadours are perfect embodiments of this sentiment. Night in and night out, Dylan and Nelson take the stage. Not as relics of days long gone, but as living proof that music, like its creators, can keep evolving long after the world expects it to. By pairing them together for a marathon tour schedule that would be a feat even for men half their age, Outlaw Fest is a historic display of past turning to present, giving way to future.
Willie Nelson and Bob Dylan will pick back up with Outlaw Music Festival for its final leg on September 5th in Bangor, ME, with dates throughout the Northeast and Midwest. Find tickets and tour dates here.