Outlaw Festival 2025 (Darien Lake, N.Y.) (Patreon)

Friday, August 10, 2025 — Darien Lake, New York

Darien Lake Performing Arts Center is quite nice for a concert venue that’s located right next to a rollercoaster. Located about 30 miles outside of Buffalo, the amphitheatre is at least 15 miles from civilization and about 15 feet from Six Flags, its parent business. Darien Lake catches the breeze from Lake Ontario in the north and Lake Erie in the west. On a good day, it’s probably as verdant a place to attend a concert as you can find in Western New York.

My girlfriend Janet and I did not visit Darien Lake on a good day. Canada’s wildfires created more smoke than Willie Nelson. As a result, the air quality in the Finger Lakes was about as conducive to good health as carrying a souvenir from Chernobyl in your breast pocket everyday. It was ostensibly a sunny day, but when I looked at the sky, it was so dreary that I thought it was going to rain. Fortunately, Janet had gotten us seats under the amphitheatre roof six months earlier. Her foresight landed me a more accessible seat and spared us both front seats to the end of the world.

We had driven about an hour from Rochester for the Outlaw Festival. I’d attended the festival the year before in Syracuse and had a semi-rotten time. My health was declining, and walking a mile to the venue from where an Uber driver had dropped me off was excruciating. Then I stood in line for what felt like an excruciating six years and had to drop off my beloved Swiss Army knife at the entrance of the venue. I never saw that knife again. The concert itself was broadly nice. Alison Krauss and Robert Plant had tremendous chemistry, Bob Dylan was more energetic than usual and played a fine set of classic songs, and Willie Nelson was sick but his son Lukas filled in brilliantly.

This year, I was pretty anxious about the prospect of Willie falling sick again. You only turn 92 once — assuming you turn 91 first — and I didn’t want to go my whole life without seeing Willie Nelson. But we arrived and hadn’t heard any bad news about Willie, so I assumed he was going to show up.

We arrived a little late — probably halfway through the opener’s set. Country singer Waylon Payne was playing a solo acoustic set of classic ballads interlaced with personal stories. I hadn’t heard of him, but I was charmed by him immediately. He spoke of old friends like Waylon Jennings and his successful audition for Walk the Line, which segued into a rousing call-and-response performance of “Ring of Fire.” It was a low-key prelude to a long night, marked by audience engagement and Payne’s charming humility. It was the sort of amphitheater show you could never see at a honky-tonk, but owed its best qualities to the honky-tonk industry.

Payne was followed by the Red Clay Strays, a country rock band who went viral on TikTok a couple years back with a sweet ballad called “Wondering Why.” The Turnpike Troubadours, a bluegrass-inflected country band with notes of Old Crow Medicine Show, played next (the highlight was “7 & 7”, which was stuck in my head for days). Both sets were roughly what you’d hope for from supporting bands: tight, catchy, and preparing you for something better.

I don’t actually remember Bob Dylan’s arrival at the concert. It’s been an eventful few weeks since the show, and I’ve lost a lot of details. But I remember that Dylan began his set with “Masters of War,” which he hadn’t played in several years. Dylan doesn’t trot out an old song without a reason, so it hit hard when I realized he was singing the old ballad where he says “even Jesus would never forgive what you do.”

But a few songs later, I began to doubt that Dylan had even sung “Masters of War,” because he was going through one unrecognizable song after another. The first half of the set had hardly any songs I knew; I felt like I was wrong to believe the first song was a familiar one. Then I realized I was sitting through one of Bob Dylan’s fabled “I Don’t Give a Fuck” shows. I had seen an excellent Bob Dylan concert in 2019 and a damn good one in 2024, so I was upset at first. My era of getting spoiled by Bob Dylan was over.

When I voiced this to Janet, I realized she was getting a magnificent kick out of it. She figured that Dylan got to coast on fumes for some shows; he didn’t have to be Bob Dylan. He could just do what songs he wanted. I came around on the show after that. Unfortunately, Dylan immediately did a 180, decided to actually connect with his audience, and started putting on an Actually Good show. We got plenty of the old hits — “All Along the Watchtower”, “Desolation Row”, “Highway 61 Revisited”, “Don’t Think Twice It’s Alright”, and my favorite, “Positively 4th Street.” It was infuriating and hilarious. I think I finally understood how some of the cooler people at the Newport Folk Festival in 1965 must have felt.

Willie Nelson came on last, and was probably the highlight of the evening. My parents prognosticated that he would suck due to being 92. I ignored them because they’re assholes, and it turned out I was right to do so. Willie looks and sings 92, but he still plays Trigger as naturally as he breathes (probably more so at this point). He’s a jazz musician trapped in a vintage hippie’s body, flowing from one song to another more than playing a distinct setlist. The show flew by. Janet pointed out that the veteran performers had the sloppiest sets of the festival. Speaks well of them, I think. Sometimes good music means showing up and fucking around. And sometimes that fucking around sounds divine.