Outlaw Festival @ Alpine Valley
POSTED:: August 24, 2026
FILED UNDER:: Concert Review
and a Backyard BBQ post-script
Aug 24, 2026
Concerts are getting pretty damn expensive, aren’t they? Like everything else? These days it feels like a miracle if you can get in to see a mainstream act for less than $100. This made the $30 lawn ticket for Outlaw Music Festival too good to pass up, especially since the Alpine Valley calendar for 2026 is sparse as usual. Due to a multitude of logistical hurdles I’ve written about over and over, the beloved venue that drew every major touring act of the 1980s is barely feasible any more for bands that I care about, so I’m extra grateful to Willie Nelson for continuing to bring his Outlaw Festival (and occasionally even Farm Aid) to East Troy year after year; otherwise I don’t know that I’d ever make it back here.
Memories of Farm Aid 2019: it rained the whole time! And that absolutely rippin’ mini-set by Neil Young & Promise of the Real made it all worthwhile. However when Willie came onstage to close out the festival, it was a little tough to witness. He seemed so frail compared to two years earlier in Milwaukee, barely playing guitar, not giving the audience much of an opportunity to sing along. I said to myself, ‘he’s 86 years old…this should probably be my last Willie show.’ But after missing his next couple of tours, the Outlaw Fest came back through in 2025, and with Bob Dylan and Sheryl Crow also on the bill, I couldn’t pass up the only enticing Alpine Valley show of the year. And when Willie came out, I was frankly stunned. He played guitar throughout and sang with a vigor I had truly missed. Maybe it had been the weather in ’19, or just an off night, but he seemed years younger at 92.
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So, how about at 93? Once again, weather threatened to dampen the fun; I loaded up the car and drove to pick up my fellow outlaws in a thunderous downpour, until we arrived at our last pickup spot in Mukwonago and suddenly the sun peeked through the clouds. There wasn’t another drop of rain in our day after that, but the forecast may have contributed to low attendance. As we walked through the gates, the ticket-scanner informed us that if we talked to that guy over there, he might have some free ticket upgrades for us. In 35 years of coming to this venue, I’d never even entered the pavilion; just call me “Lawn Boy”, I don’t see much of a need to pay more money to hear the same concert. With the threat of rain still in play, though, we figured it wouldn’t hurt to inquire. Seeing as I’d just turned 50, and this was my 50th Alpine Valley concert, I guess I was due to finally see the stage a little more clearly.
Still, the freedom to move around is a major benefit of lawn life, and since one member of our group was here for the first time, we spent the first few acts on the grass. We’d arrived just in time to miss Don Was & The Pan-Detroit Ensemble; I’d mistakenly thought that would be one of the later acts, so I’m still…completely mystified as to what the point of that project is. We already have quite a few prominent Grateful Dead tribute acts going, and while I was curious to see this one, I guess it’ll have to wait. Besides, if I’m going to see Don Was, the only song I REALLY want to hear is “Dad I’m In Jail”, but I’m pretty sure he doesn’t play that one.
So our afternoon started with Sierra Hull, a solid set of rootsy country featuring a tight band and good songs. I had heard her name before but didn’t know any of the tunes except the cover of Tears For Fears’ “Mad World”. While she was playing, one of our crew ran into an ex-neighbor who was here solely to see Stephen Wilson, Jr., the next performer of the evening. Wilson’s latest release is a covers EP called BLANKETS, featuring countrified versions of ‘90s alt-rock nuggets (and a Postal Service tune). While he didn’t play any Nirvana or Temple of the Dog songs at Alpine, he did begin his set with the intro to Hum’s “Stars”, not sounding very much like country at all. His set was a pretty cool mainstream-twang/grunge hybrid, though, the Eddie Vedder influence very apparent as he sang. I spent the latter part of his set getting food in the pavilion (fries: thumbs up; burger: thumbs down), so perhaps I missed the explanation regarding the name “Gary” but there was some extended banter about it and I spotted at least a couple t-shirts referencing “Gary” as well. That was my main takeaway: Stephen Wilson, Jr. really loves his father (R.I.P.) and people named Gary.
Next up was Lukas Nelson, the second of Willie’s sons to perform (we missed Particle Kid, who’d opened the day’s festivities, possibly while it was still raining; that’s the stage name of Willie’s youngest son, Micah, who would pop up again during the closing set). Lukas may be Willie’s most famous offspring, yet as a country troubadour he remains almost deliberately in his father’s shadow for the moment. Until recently, he’s been known primarily as part of Willie and/or Neil Young’s bands, although Promise of the Real released eight albums (and three more with Young) before Nelson put the group on indefinite hiatus two years ago. There’s a Willie-esque quality to Lukas’s singing at times, but he’s more reminiscent of an extra-robust Hank Williams, Sr., really. He bowled me over last year at Summerfest, and although he didn’t fully let fly with those powerful pipes until the end of his set at Alpine, I thoroughly enjoyed the whole thing. Especially delightful was a smooth rendition of “Althea”, a pleasant surprise for those of us who figured we’d already missed all the Dead covers.
For The Avett Brothers, we decided to take advantage of our row W pavilion seats. All these years, I’d only seen the huge hood of Alpine from behind; I can’t deny the surreal feeling I felt looking at it from underneath. Scattered throughout it you can see dozens of light-colored patches where the ancient wood was presumably wearing thin or cracking, and it got me thinking, once again: how many more times will I even be here? How long will repairing this old shed remain financially feasible? Five concerts a year ain’t gonna cut it I’m pretty sure, and with ‘the neighbors’ seemingly ambivalent about the merits of that gosh darned rock and roll music, I fear I’m gonna see the place torn down in my lifetime. A profoundly sad thought, but it was only gratitude rushing over me Friday; a couple weeks ago I was expecting to be coming here solo, yet I’d managed to rustle up a Riverwest posse in short order, and it seemed like everyone was having a great time. There are tons of other classic amphitheaters in the U.S.A., but Alpine’s the only place in Wisconsin where you can have this kind of fun.
Given only an hour slot, the Avetts’ set was rather chill compared to some other performances I’ve caught, yet still a superb and occasionally raucous display of musicianship. They’re known to bust out the occasional cover, mostly very old roots/Americana material, but they’ve been working in a bunch of new ones this summer: Roger Miller’s “King of the Road” got a major rise out of the ahem less-youthful members of the crowd, while iconic bluegrass standard “Foggy Mountain Breakdown” got EVERYBODY revved up. Then came another treat: the Dead’s “Ripple”, an emotional singalong for lots of attendees. Like Nelson with “Althea”, the Avetts had debuted all these covers at Red Rocks last month, and it certainly felt appropriate to honor the original outlaws of Americana in the wake of Bob Weir’s passing earlier in the year.
The Avetts also played Toby Keith’s “As Good As I Once Was”, but that’s been in the repertoire for a few years; the rest of the highlights were their own tunes, particularly the opener of “Satan Pulls The Strings” and the delirious “Laundry Room”, the only song they’ve played every time I’ve seen ‘em (and I wouldn’t have it any other way). Shout-out to Mickey Raphael as well, the harmonica maestro from Willie’s band who augmented the Avetts to great effect. Even the kinder, gentler Avett Brothers know how to rip it up when they need to.
Before Willie actually came onstage, the video screens played a montage of patriotic images set to his recording of “Living In The Promiseland”. It’s easy to forget, but there was a time when left-leaning Americans still felt pride in their country, a feeling that’s hard for these old guys to shake, particularly during the U.S.A.’s 250th year apparently. Then the curtains fell to reveal Willie seated with his two sons and Waylon Payne, whose father Jody had been a member of the Nelson touring band for over three decades. A four-piece backing band accompanied them from behind as well, as they ran through about an hour’s worth of mostly songs any Willie fan would know and love.
It’s always a little strange, though, how few of these tunes he actually wrote. A man with a truly distinctive voice as a writer, he’s generated incalculable royalties for other people by making their songs iconically his own, a fact not lost on his sons. Lukas regaled the crowd with the tribulations of dating a gal named Georgia, performing his own “(Forget About) Georgia” in humorously moving tribute. Then there was Micah’s “Die When I’m High (Halfway To Heaven)”, which he’d attempted to transport himself into his dad’s headspace to write (and absolutely nailed it). But the most heart-wrenching father-son duet of the night had to be Lukas and Willie doing “Just Breathe”. This was actually the third time I’ve seen the song performed—each time right here at Alpine. Last time Dave Matthews came here, he played it as an encore; the other time it was the guy who wrote it, Vedder himself, at the Pearl Jam festival in 2011. The two Nelsons originally recorded the duet for Willie’s 60th album, HEROES, back in 2012, and if any latter-day Vedder composition deserves such esteem, this is it; it may be the last great song he’ll ever write, and it always stabs me right in the heart.
As the set wore on, it struck me that perhaps it’s not just age-related frailty or health issues contributing to Willie’s halting, unpredictable singing, but the emotion of these words and melodies. Many times during the set he wiped at his eyes; how does a person, for example, even get through “You Were Always On My Mind”? My throat tightens up just typing those words. Dozens of people recorded it before Willie, but when I think of the song, it’s only his voice I hear; it just seems like something he would’ve written if he’d thought of it first, and as a man who’s spent his whole life on the road (again), just imagine how many people he could have in mind while he’s singing it.
Willie wasn’t as vigorous on this night as he was last year at Alpine, but I’ll remember this performance as dearly as any. It was my own dad who first got me into Willie when I was a kid, and surely there were plenty of parents at this show who dragged their kids along for potentially one final chance to see one of the most legendary singer/songwriters in American history. And lots of ‘em probably got the surprise seat upgrade as well; regardless of how many notes he sang or played, this Outlaw Fest was just about the best experience thirty bucks can buy.
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Yes, $30 was a steal, but the show the next day at Humboldt Park in Bay View was free, featured way better and way cheaper food and drink options, and arguably even a better lineup of music. WMSE’s Backyard BBQ is always a marquee event as the Milwaukee summer winds down, but this year’s edition was one of the best I can recall. There were threats of rain again; at one point during Superchunk’s headlining set the wind picked up fiercely under darkening skies, but the clouds never burst; the only real complaint anyone might’ve had was regarding the various bugs swarming around. It was a gorgeous day and night and everybody was there; I heard most of Known Moons’ set (although I was catching up with radio friends during it), and a surprise Mark Waldoch appearance for the beginning and end of Field Report is a guaranteed win, but Superchunk wasn’t even the marquee event: the night ended with a Sylvan Esso DJ set. Normally you’d have to endure 18 hours or so of Bonnaroo, chemically enhancing yourself to stay awake until 2 a.m. to catch something like this. The crowd was abuzz all day: what will it be like? is Amelia even here? will it just be beats? what if they do the whole new album?? And while some attendees were evidently bummed that the duo didn’t play the hits, I don’t get those people. Haven’t you already heard those songs a ton? What Amelia and Nick gave us was way cooler, a totally engaging and wide-ranging hourlong dance party, with OCCASIONAL bits of vocals. They even brought along vinyl copies of the new album, three weeks before it comes out! All in all an incredible gift to the city of Milwaukee, and another night I won’t soon forget.
You can read more of Cal Roach’s reviews and writings here