I still have the poster from the event. A rare, if not once in a lifetime concert was held in my hometown of Pittsfield, Massachusetts, at a baseball park no less. Frankly, I was surprised when I heard about it. It’s not like these big-time musicians, legends really, were doing a gig at say the Hollywood Bowl in Los Angeles, California. City-owned, Wahconah Park is situated in the heart of a working-class neighborhood. Constructed in 1919, the stadium has a 4,500-seat capacity that has hosted mainly minor baseball leagues over the years.
From my journal: June 18, 2005, Newbury Park, California
“Going home…Ray got tickets! The show is Thursday night!”
Anytime I have the chance to visit my family where I grew up, I take it. Spending time with those who know me best, and love me anyway, and in the place that shaped me and holds my childhood memories is always worth the cross-country trip. And to experience these renowned singer songwriters live, alongside my family, bonus!
So, it was on a warm summer evening, 20 years ago, on June 23rd to be exact, sitting in wooden grandstand seats, surrounded by the Berkshire Hills with Robert, my mom, brothers, sister-in-law, and a longtime friend, that the concert kicked off with an upbeat folksy performance by the Greencards, a bluegrass band from Austin, Texas. A half hour and set change later, the first of the big names appeared on stage.
Seventy-two years old then, I wondered would he still be able to engage the crowd, maintain the energy needed to play his guitar, sing, and tell stories for a good 60 minutes? Accompanied by his band, which included several family members, Willie Nelson delivered a lively set of favorites new and old in his warm and conversational style. Songs I knew by heart like, “Mamas Don’t Let Your Babies Grow Up to be Cowboys”, “Georgia on My Mind”, and “On the Road Again” transported me back to my high school years and to our house on Indian Street where I learned them.
Next it was time for the lead act. His signature gritty voice could only belong to one person. Bob Dylan. I was introduced to his music by my 5th grade teacher, Mr. Carman who taught us the song “Blowin’ in the Wind”. While the sixty-four-year-old Dylan didn’t sing that tune, he did perform 12 others including “It’s All Right, Ma I’m Only Bleeding” and “Highway 61 Revisited”. The encore had us all up on our feet, singing along to “Like a Rolling Stone”. Indeed, it was “The Bob Dylan Show” as it was billed. What a night of entertainment!
From my journal: April 29, 2025, Newbury Park, California
“Robert got tickets…playing together mid-May…wow!”
Anytime we get the chance to catch up with friends while listening to live music, we take it. Spending time with folks who really appreciate music connects us even more. And hanging out at the iconic and largest outdoor amphitheater in the U.S., well, not much else compares. With its 17,500-seat capacity, the 103 year-old Hollywood Bowl is larger than life! The high caliber of talent showcased is never short of spectacular.
So, it was on a chilly spring evening, 20 years later, May 16th to be exact, sitting in a 4-chair box seat, surrounded by the Hollywood Hills, with Robert and two longtime friends that the concert kicked off with the sounds of Sierra Hull, a bluegrass singer and mandolist from Nashville, Tennessee. Her upbeat music set the mood for the evening. Next up was Billy Strings. Also from Nashville, he’s known for his improv skills. Such a phenomenal bluegrass singer, guitarist, and banjoist! Three hours and a set change later, the first of the big names stepped into the spotlight.
Eighty-four years old now, I wondered if his gravelly voice would still let his poetic lyrics shine through. Would his piano playing be sharp? Would his harmonica notes be clear? Dressed like an outlaw, Bob Dylan opened this leg of “The Outlaw Tour” with “Things Have Changed”. With nine albums released since we saw him last, the songs performed were not all familiar. But a few like “All Along the Watchtower” and “Simple Twist of Fate” were, just reshaped. Like before, he said little between numbers, except to ask someone what they were eating! He closed out his set was “Don’t Think Twice, it’s Alright” to rousing applause by the multigenerational crowd.
Next it was time for the lead act. It was just after 10 p.m. when 92-year old Willie Nelson took center stage. I wondered, how would his trusty guitar Trigger sound? How many songs would he have the stamina to perform? Would he still engage us with song and life quips? Once again joined by his family band, wearing his signature red banana, he proved to stand the test of time. Starting with “Whiskey River” he took us on a journey through a 21-song set! Though he’s released 32 albums since we first saw him, he sang many tunes fans know and love. Like “Help Me Make it Through the Night”, “Angel Flying to Close to the Ground” and “You Were Always on My Mind”. The night ended with Sierra Hull and Billy Strings playing with him on “Will the Circle Be Unbroken/I’ll Fly Away” and “I Saw the Light”. What a night of entertainment!
To say I was astonished at the end of the concert was an understatement. Bob Dylan has been writing and playing music for 70 years and Willie Nelson has been doing what he does for 85 years! To still be having careers that have spanned some people’s lifetimes, to still be creating new music, and to still be selling out shows, that’s something, really something.
The first time I saw them tour together, Bob Dylan and Willie Nelson were what most people would consider retirement age. So maybe that’s why I wondered about their abilities, their longevity, their staying power. But here it is even 20 years later, and they are still out touring, still giving it their all, and still connecting people in the powerful way that only music can. Seeing them once in a lifetime is amazing, twice in a lifetime is extraordinary.
A Journal Journey 