MUSIC: ALPINE OUTLAWS

A hard rain did indeed fall at Outlaw Festival 2025.

I am still processing the experience.

Talk amongst yourselves.

In service of Linda Richman’s SNL Cawfee Tawk, I will give you a topic: Uggs should never be worn on feet or toilets, but for some reason when I see them, I like to call them “foot toilets.” Discuss amongst yourselves.

Let us begin the homily.

I don’t remember my baptism. For one big reason, I was less than one year old. It happened in a Catholic church where I eventually attended and became an altar boy, but the actual birth was lost on me. I’m sure I cried. I’m confident I pooped. And hopefully, every once in a while, I smiled like a little Irish magpie, squawking and hawking my wares to the wild, the innocent, the B Street Shuffle of Reedsburg, Wisconsin, aka Butter Capital of the World.

The bicentennial nature of being born in 1976 provided me with enough Americana I can say, with little contest, a big part of me was born on Friday, September 19th, in East Troy, Wisconsin, when I attended the Outlaw Music Festival on its final leg of a brief tour.

But before we get to East Troy, why not stop by the largest Culver’s in the world, located just outside Edgerton, WI. Jessie and I share a healthy laugh over the first time visiting a Culver’s together, when I had “accidentally” ingested a 100mg gummy about three hours before. But that’s another story for another outlaw festival, dear park rangers.

Two riders were approaching. And the wind began to howl. (Photo: BB)

Seeing Willie Nelson and Bob Dylan live and in the flesh is something I have somehow successfully avoided my entire life. How? Why? Did I have a lifetime fever or something? Was I in some kind of carbon-freezing chamber in Cloud City? Or was I just plain scared of the truth: that Bob Dylan and Willie Nelson — real-life folk heroes — were somehow capable of sharing the same space and time as all of us, somehow larger than life and yet right there before our blue eyes crying in the rain, not thinking twice and just telling us it’s all right.

If I have offended any of you, please consider this my sincere apology. I mean, come on, he even played “Bloody Mary Morning” for us. As the author of that book I felt like this was my music baptism. To re-emphasize, I still feel like I had not yet lived and was born on the 19th of September, 2025.

Actually, my sweetheart of a brother, Rob Bartels, who attended the same show, always brings up the same memory of me as a baby: “Oh my God did you sweat. I have never seen a baby sweat as much as you. Just…endless.” (Editor’s Note: Rob didn’t really know about Bootwood. When he opened his email messages before the show and showed me my last email post and said, “Is this you?!” that means there’s a good chance he’ll never read this post.)

Now. The Show.

Alpine Valley is located in East Troy, Wisconsin. It’s farmland. This ain’t no disco. It ain’t no country club either. Everyone I spoke to mentioned three things to expect when attending Alpine Valley: expect to pay $22 for a beer, wear comfortable shoes because it’s on a hill and therefore incredibly steep, and prepare for an incredibly long time exiting (upwards of 2 hours).

We entered the hallowed gates around 2:45 PM. Plenty of time to meet my brother and his wife and experience a Wisconsin pastime like no other: The Tailgate. Alpine did not disappoint. Healthy grass (on the ground), lawn chairs, coolers, portable grills, snacks galore, MJ Lenderman koozies, open hatches on the backs of every other parked car, bean bag toss, people cranking Willie and Dylan, and good company.

Family. (Photo: Rebecca Bartels)

Roll me up and tailgate me when I die. (Photo: BB)

We left the tailgate at what we thought was a favorable enough time to catch opener Madeline Edwards, but sadly (and luckily) after stopping by three different merch tents we landed our seats right when Waxahatchee’s opening music, Dolly Parton’s “Here I Am.” We grabbed a beverage and hit our seats and grinned like a couple of giddy 1963 teenagers waiting for the Beatles.

I couldn’t believe I was going to see Bob Dylan and Willie Nelson, and to make it even more special Waxahatchee and Sheryl Crow were going to open those doors.

“There are some who can live without wild things and some who cannot.”

— Aldo Leopold

There are only quick “reviews” here. I’m not going to labor over how great these artists are, because you already know that. This article is really about the overall experience of being a first-time caller long-time listener of Alpine Valley.

• WAXAHATCHEE: First off, we have one framed photo in our kitchen. It is a 22 x 14 image from late August 2024. And it’s from the first time Jessie and I saw Waxahatchee. Katie Crutchfield wears shiny silver boots and strums a hollowed out black acoustic Gibson J-45 as a reincarnate amalgam of Lucinda Williams, Loretta Lynn and Gillian Welch all rolled into the sonic swagger of her original self. In this house, you love three things: The written word, those insanely addictive dark chocolate peanut butter cups from Costco, and Waxahatchee. If you have never seen them live, please seek a nearby tour and give yourself the treat of watching a terrific band and one of the best young singer-songwriters making it look easy and having a wonderful time along the way. They rolled in when the sun was still out and put their stamp on the special evening by simply playing as though they were headlining.

  

  “And I held it like…a penny I found…” (Photo: BB)

• SHERYL CROW: Nothing but sunshine from the matriarch of feel-good radio play. I had never seen Sheryl before. She did nothing but bring the sun and we soaked it up every which way we could find it. (Don’t. You. EVER. Sass. The. 90s.) I confessed to Jessie I might scream if she played “My Favorite Mistake.” (She did. I didn’t.) Sheryl jumped, ran, clapped, and revved up the crowd’s engine with never-ending feel-good moments from front to back. She was the perfect choice for representing the female artists who deserve more of our praise and recognition for paving the way for future generations of female singer-songwriters. Every song in her setlist was pure magic. Bless her heart for bringing out Waxahatchee for a fun-loving “Everyday Is A Winding Road” and stressing how the crowd needed to pay attention and support young artists like Katie and Team Waxahatchee.

  • Bonus: Sheryl did the robot. Multiple times.

    “I got two teenage boys who just love seeing their 63 year old mom dancing around.” — Sheryl Crow

    

    Not a bad source of fuel for a 6 hour concert on a steep hill.

    

    Dylan. Somewhere in the middle of the music. (Photo: JF)

• BOB DYLAN: Okay, here is an incredible feat: to my limited knowledge there has never before been a lounge act who played for 23,900 people. That sounds like a diss. It’s not. The Word Doctor just turned 84 years old, good people of Bootwood. The modern-day version of Dylan quietly and moodily walked out and performed a legit 1:20 set where he stayed behind a grand piano wearing a poncho with the hood up, and while every other musician had video monitors showing close-ups of the band on stage, Dylan’s set had no close-ups. Everyone heard Bob Dylan, but did everyone see him? No. He’s still an enigma wrapped in a riddle while harmonica-squealing a conundrum from his back pocket - the pockets we never see. Everyone has an opinion on Bob Dylan. But here is what makes him so iconic: No two opinions are alike. If you get someone who has spent time with Dylan beyond the “Our greatest living songwriter” to “He’s great” or “I can’t stand him” there’s hidden depth and significant variation. That is an icon. He is backed by an incredibly talented band. Everyone showed up. No words were spoken between songs. And I will never get over how they ended their set: they all stood, walked to the back of the stage, and faced the crowd, their dark silhouettes motionless for a beat before they shuffled off. My uncle Cy once told me he was visiting Greenwich Village in 1961 and saw a chalkboard sign outside a cafe saying “Bobbie Dylan” and caught him live. I felt seeing him on Friday in 2025 somehow connected me to the memory of my dear uncle, someone who was a poet to me even though he never wrote a song like “Desolation Row.” Dylan finished his set and a hard rain fell for about 10 minutes, with some people leaving the Willie set early, which was a huge mistake.

  

  Baby’s first Alpine. (Photo: JF)

  

  Uncle Willie and Trigger. American legends. (Photo: JF)

• WILLIE NELSON & FAMILY: I had heard stories. People told me Willie gets wheeled out. “He’s old.” “He barely sings.” “He just sits there.” I can successfully report I will never forget the first time I saw Willie Nelson live, and I hope it is not the last. The opening of his set was a video from a 1986 video “Living in the Promiseland,” depicting a time in America when we were more open to the fabric of our global ambassadorship. Willie was 53 in that video and is now 92 years old. And we are still here, in America, wishing the dream we had as kids rings true for not only ourselves, but our family and everyone else we experience. He still plays Trigger, his famous acoustic guitar, with a hole knocked out near the bridge from years of strumming. Willie came out around 9:30 and played like he was ready to sing and strum all night. I loved the backdrop of a giant American flag. I love the idea that someone like Willie can bring people of different political shades and ideologies together, and through music we can simply enjoy what makes this country so great. But the one thing that will stay with me was remembering the look on Willie’s face between songs. He is clearly someone who loves America like we all do, and yet I couldn’t help but think how he looked like America has been feeling lately: weary, uncertain and short of breath. Like everyone else in America, I was raised on Willie Nelson through radio, TV, vinyl, 8 track, cassette tape, CD and through our digital age. We were all raised on Willie whether we wanted to hear him or not. And I am so incredibly humbled and grateful I got a chance to finally see him. When any goober (like the former me) asks me about how he was at 92 I’ll stand proud and say, “He changed my life.” Thank you, Willie.

  

  Stay all night. Stay a little longer. (Photo: BB)

• THE CREWS: Lastly, I want to give a proper shout out to the crews. For such a big production of rotating talent the switches between sets couldn’t have been more seamless and exemplary. I’ve observed artists calling out their road teams more lately, and many of you who go see live music know that is often rare. It clearly takes a village to get the lights, wires, microphones, band needs, and overall sound ready from one line-up to the next. Bravo to one of the most impressive nights of transitions I have ever experienced. I would happily follow The Outlaw Crews if they ever toured!

My only complaints:

• Not enough Waxahatchee merch in the Concert Gear tents.

• This Sour Patch Kid outside the entrance:

  • 

    If it makes you happy, it can’t be that bad. Unless you’re standing outside the Alpine VIP entrance directing traffic. Then 1) You are definitely not happy and 2) Everything can be bad. This ham sandwich gave me the stink-eye for taking his photo. Maybe that was one of Dylan’s kids?

• Too many people getting up and walking around during Dylan and Willie. In fairness, there were limited bathrooms in the area we were seated, and Alpine would do itself some good (A “Change Would Do You Good” perhaps…?") to install a few funiculars for the elderly, but really, what the hell is going on that so many Cowboys let their Babies grow up to be Lame-O’s.

I am going to think about this concert experience for a very long time. I don’t know if I will ever get over it. Jessie and I see music on a regular basis, and for nearly every cathartic live performance produced by a band or an artist getting onstage and putting out their sounds, their lyrics, their soul, and their hearts, what more can be said of the honor and privilege of seeing American history: Willie Nelson, Bob Dylan, Sheryl Crow, Waxahatchee, Madeline Edwards, and all of us: The Family of Music Lovers.

“I have never seen a baby sweat as much as you. Just…endless.” — Rob Bartels

I don’t wanna grow up, because if I did, I wouldn’t be a Willie Nelson kid.

Too bad I didn’t have any foot toilets around when I was a kid to pick up all that baby sweat.

Outlaw Music Festival, Alpine Valley, September 19th, 2025. (Photo: JF)