Rock ‘n Roll Road Trip on a Harley-Davidson Street Glide
Back in elementary school when other kids were listening to songs like Baby Beluga and Wheels on the Bus, I was poring over my parent’s classic record collection. Sifting through dusty old boxes of vinyl, I would sit cross-legged on the basement floor as I voraciously traced back the roots of rock ‘n roll, one crackly old record at a time.
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Carefully placing the needle down would magically unveil a whole new world of wonder and musical discovery. I would carefully study the jackets, looking for clues of who these musicians and groups were. The greatest revelation of all was the discovery of a similarly scrawny, spectacled boy from Lubbock, Texas. Born Charles Hardin Holley, he officially adopted his childhood nickname of ‘Buddy’ and shortened his surname to Holly.
I obsessively consumed his robust and enduring body of work. By then I had become vaguely familiar with gospel, rock, blues, country and western, but this was all of them put together in a melodic collection of sounds that was unlike anything I’d ever heard before. Even now I can’t help but wonder how a middle-class kid from West Texas magically used his Fender Stratocaster guitar to cosmically channel so many distinctive sounds that defied genre, race, space and time over only a few short years.
The curiosity and excitement continued to swell before crashing down with the discovery of his premature and terribly tragic death at only 22-years-old, along with Ritchie Valens and J.P Richardson, known as the Big Bopper. For those that don’t know the story’s details directly, chances are good that most people have seen the film La Bamba or heard Don McLean’s song American Pie that recounts ‘The Day the Music Died.’
In addition to our mutual optical challenges and fondness for fine suits and music, Buddy and I also share a common passion for motorcycles. He was famously turned away from a Dallas Harley-Davidson dealership by a salesman who didn’t think he could afford to buy a motorcycle, only to enter a neighboring dealership to buy three – one for himself and another two for his bandmates that were with him. They donned their Brando-like biker caps and rode them back to Lubbock in a thunderstorm.
Having a much more modern and comfortable 2025 Harley-Davidson Street Glide to review and some free time on my calendar, I dedicated my summer vacation to making a somber pilgrimage to prominent locations in Holly’s life and final days. I wanted to learn more about the man, how he lived, and see where he played his last show. I also felt deeply compelled to pay my respects where his life came to an end.
Over the years, I have sought out every possible piece of work related to his life, including books, albums, and documentaries. I’d even traveled to Lubbock, Texas where he was born and spent his formative years. I visited his childhood home and high school, the small museum in his honor, and the performing arts center that bears his name. The long journey included a solemn visit to his final resting place, a spot marked by a modest gravestone in a long-forgotten cemetery on the outskirts of a town in decline.
The more I learned about him, the more heart-wrenching his story became. The fact that he had just recently been married and was expecting a child, that his trusted band had parted ways, and he had only joined the ill-fated Winter Dance Party tour out of necessity because his agent Norman Petty had tied up all his money in other investments. And perhaps most notably that his life was so violently cut short in the horrific and mysterious crash of a small plane that should never have taken off in the first place – for a myriad of reasons.
Setting off in the scorching late summer heat straddling the Street Glide’s 117 cubic-inch Milwaukee-Eight engine, it was difficult to imagine the dreadful conditions members of the Winter Dance Party suffered making the trip in rickety old buses in the icy depths of winter in 1959. Enduring multiple mechanical breakdowns, frostbite, and flu during the poorly planned tour that had them criss-crossing the barren Midwest, Holly made the fateful decision to charter the private airplane to fly him and his band to the next city on the tour rather than travel overnight by bus.
Among the early architects of rock ‘n roll, Holly’s influence on popular music has been cited as significant inspiration by everyone from Eric Clapton and The Beatles, to Jimi Hendrix, Elton John, and The Rolling Stones. Music as we know it today would not be the same without his contributions.
Touring the Rock ‘n Roll Hall of Fame in Cleveland, I was stunned and saddened to discover the precious little attention paid to Holly’s brief, albeit prolific and influential career. A member of the inaugural class of honorary inductees when the Hall first opened, the only remnants of his all-too-brief career are a small plaque and a copy of his first album with his backing band, The Crickets.
Leaving Ohio, I continued my physical and spiritual journey through Illinois to the sprawling countryside of Iowa. Humming along the highway tucked in behind the iconic Batwing fairing, the Street Glide’s 105hp V-twin had no shortage of gusto as urban environments were replaced with suburban sprawl then wide-open highways lined with farms and flowering fields.
The sleeker, more aerodynamic bodywork was achieved through what Harley calls computational fluid dynamics (CFD) to reduce wind buffeting and help the Street Glide cut through the air. The updated 12.3-inch touchscreen TFT display connected to Apple CarPlay via the USB-C in the dash-mounted smartphone tray, presented turn-by-turn navigation and allowed me to play my curated playlists though the 200-watt speakers.
The intoxicating scent of warm summer rain was wafting across the fragrant breeze as I approached Clear Lake, the location where the musicians played their final show. The clouds eerily parted to beam an ethereal glow above my destination in the distance as the sun lowered in the sky and disappeared below the horizon, as if opening heaven’s gates to welcome me in.
Following the street signs bearing the names of Buddy, Ritchie and J.P., I approached the legendary Surf Ballroom. Entering the historic building felt like travelling back in time. If rock ‘n roll is to be considered a religion of sorts, which I believe it is, then the Surf is surely sacred ground. Plaques, pictures, artifacts and exhibits are on display, chronicling the musicians’ tragically short careers and details about their final performances.
I spent hours looking at every photograph and piece of memorabilia, reading every account and tribute. Standing on the stage where Holly played his final song and walking through the very dressing room where the infamous coin flip was made to decide the final seat on the plane felt surreal. Seeing the phone booth where Holly made his final call to his wife Elena and Elwin Musser’s camera that captured the scenes of the iconic crash scene the following morning, brought the stories I had read about into stark, vivid reality.
The Surf Ballroom has embraced the unthinkable tragedy that transpired in Clear Lake by transforming it into a celebration of the musicians and their enduring legacy. The Three Stars Plaza is an interactive artistic installation that allows visitors to enjoy their music, while the newly opened Not Fade Away exhibit creates an immersive environment where guests are transported back to that fateful February night.
I then retraced their journey to the Mason City Airport where the doomed flight departed from and where the plane’s owner Jerry Dwyer stood as he witnessed the aircraft disappear over the horizon. Riding up a rural gravel road just a few miles away, a large pair of Buddy Holly’s iconic glasses mark a beaten path into a farmer’s field. About half a mile from the road sits a small memorial where the plane’s twisted wreckage came to rest on that cold, snowy night so many years ago. A second memorial was subsequently installed to honor Roger Petersen, the young, inexperienced and unqualified pilot who was flying the plane.
Sitting in silent contemplation in the vast Iowa cornfield, I witnessed a steady stream of retired couples, teenagers, and families with young kids park at the side of the road and approach the memorial to quietly pay their own respects. Witnessing travelers of all ages visiting the Surf and the remote cornfield gave me comfort that Holly, Valens, and Richardson’s music will continue to be heard and enjoyed by future generations.
Following the path back out to the road, I felt a profound sense of sadness for the young men and their families. I pondered what could have been had their lives not been so tragically cut short. The experience made me even more appreciative of the music that remains.
As I set off on my long, grueling journey home, I selected my favorite Buddy Holly album and turned up the volume to hear those comforting, familiar sounds I first discovered as a young boy. With fresh air in my lungs and the warm sun on my face, I couldn’t help but smile.
There is a saying that proclaims everyone dies three times: first, physically, when their heart stops beating; a second time, spiritually, when they are buried or cremated; and finally, when the last living person says their name and their memory is lost.
I’ll continue to enjoy his music and speak his name. Thank you, Buddy.
Dustin Woods
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