Woodstock 50’s Doom and Gloom: Caught in a Devil’s Bargain

A crowded music festival market and the changing tastes of younger generations means the Woodstock has lost a lot of its cultural cache and may no longer be so relevant to music fans.


Marshall Amp by tookapic (Pixabay License / Pixabay)

Anyone who has spent time on a highway knows about the annoying and alluring phenomenon of rubbernecking. An accident happens, and suddenly there’s traffic because everyone slows down in the hope of seeing some grizzly details. Think of Woodstock 50 as a hundred miles of rubbernecking with one horrendous wreck after another happening. Woodstock 50 didn’t have the grace to end it all in a day, instead dragging out for month after painful month this year until it finally collapsed and thankfully died. Reading the ongoing story of the unrealistic farce, you felt some pity for it, like a wounded animal that needed to be put out of its misery.

The recap stories about Woodstock 50 will focus on all the bad decisions and planning that the organizers made over five months in March to July 2019. Those stories push the line that the recent flubs wrecked the name/brand/ideal of the original 1969 festival. The only problem with this narrative is that it’s simply wrong. Woodstock Enterprises was a deeply flawed organization from the get-go, including its mythic first fest. They proceeded to chip away at their own legacy over the years with a bunch of forgotten and failed follow-up fests. That culminated in the 1999 fiasco and flaming out with the 2009 ‘Heroes of Woodstock’ tour that no one seems to remember. The Award-Award winning documentary and the Crosby, Stills and Nash hit drew a golden, Aquarian halo around the original Bethel shindig. But Woodstock 50 was more part and parcel of the whole Woodstock debacle than its die-hard fans and the promoters would like to admit.

Even before Woodstock 50 was going to be rolled out this past spring, it was already facing its own competition, much as it did in 1979 with another ‘Woodstock’ then. What was dubbed ‘the High Country Woodstock’ was planned in North Carolina but ran afoul of Woodstock Enterprises because Woodstock Enterprises claimed that the Tar Heels would infringe on their name and confuse consumers. That left the North Carolina promoters to change the name from ‘Woodstock Experience’ to ‘WE2019’ and carry on regardless with a line-up that included the remnants of Canned Heat and Ten Years After, plus Jefferson Starship (headliners of the ‘Heroes’ tour) and the ever-present John Sebastian. Unlike Woodstock 50 though, WE2019 did actually happen.


For anyone who hasn’t spent time in upstate New York, you’re missing something, at least during the middle of the year. Having gone to school in the Finger Lakes region, I lived through four years of freezing weather and lake-effect snow that went on for six to eight months a year. But during the late spring and summer, it really is an idyllic area. It’s dotted with nice little wineries, wonderful farms, great hiking areas, beautiful bodies of water to swim in, endless leaf-peeping, and something of a sweet New England vibe to much of it. Not exactly the ‘garden’ that Crosby, Stills and Nash popularized but its charm and warmth are undeniable, even in the MAGA regions. No doubt that this bucolic locale lent the original Woodstock a lot of its appeal and endurance, not to mention its convenient location just a few hours from New York City and New Jersey.

Ironically, the town of Woodstock, New York was originally intended as the site of the 1969 show but never hosted any of the subsequent music celebrations. Instead, it’s quietly existed as an artist reserve which was slowly inhabited by rock musicians who flocked there in the late ’60s (Dylan, the Band, Van Morrison, Tim Hardin) but who wisely didn’t try to overtake it. Later, the town became the domain of glam-tastic artists like David Bowie and the B-52’s and assorted cultural misfits.)

Because Woodstock is associated with the upstate region, Lang kept most of his later-day fests somewhere in the area and planned Woodstock 50 to happen there too. He first plotted it at the Finger-Lakes region Watkins Glen International raceway, the site of the fabled 1973 Grateful Dead/Allman Brothers/the Band show which broke Woodstocks attendance record. As such, Lang was all smiles on 19 March 2019, when he held a press conference in New York City with Woodstock alum John Fogerty and Common to announce W50. They also planned another three-day cross-generational line-up that included headliners like Jay Z, the Killers, Dead and Company, Miley Cyrus (who would have been great reprising her Black Mirror character like she did at Glastonbury) and the ever-present John Sebastian. After planning had begun at the start of the year (just as it did in 1969), the acts were set and the venue was set so what could go wrong? It turns out, a lot could.


Even before getting into all of Lang’s mistakes this year for Woodstock 50, there were some logistical considerations that he obviously didn’t mull over. ‘Woodstock’ still manages to be a noted brand name nowadays even faded off from decades ago. But the Boomers would have no illusion that Woodstock 50 would be in any way like Woodstock 1969 and the only big draw for them would be Santana, the Dead, and maybe Fogerty, all of whom tour all the time otherwise. That’s not even mentioning how traveling upstate and camping out for three days ain’t as easy for an older crowd now. As for millennials, Woodstock predates them, so that it doesn’t hold the luster for the Gen X/Y/Z crowd that it would for some of their parents/grandparents. Millennials also already have their generational festivals like Coachella, Bonnaroo, Lollapalooza, Pitchfork, and Afropunk for starters. What would Woodstock 50 have to offer that’s special or different other than the name brand?

Could Woodstock 50 at least have some appeal to jam band fans? Jesse Jarnow, who did the excellent liner notes for the recent comprehensive Woodstock 1969 boxset, was skeptical to say the least:

“I don’t think Woodstock 50 had any more appeal to jam fans than, say, what Bonnaroo has become. Jammy acts feel like demographic obligations on both schedules at this point. The (planned) middle day of Woodstock 50 had a nicely eclectic vibe that was more like the current version of the Newport Folk Festival, which is more jam-adjacent without actually being jammy. But on paper, to me, the Woodstock 50 lineup just felt filled with canned Coachella-type sets, plus a few nods towards the original lineup. I only count two bands on the Woodstock 50 poster that were likely to improvise for more than five minutes at time, Dead & Co. and Hot Tuna, both with San Francisco 1960s roots. I suspect jam-inclined listeners — and those who enjoy taking psychedelics at festivals — bend way more towards the smaller, less corporate festivals that leave room for spontaneity, like Summer Camp or Electric Forest.”

The whole idea of a legacy show is a tough sale for a lot of other reasons too, especially past and present perceptions, as event producer Molly Small explains. Her advice?

“Don’t do it. Trying to recreate something that is beloved is an uphill battle. Outdoor concerts are hard enough. The expectations from those who experienced it previously are impossible to meet, and new attendees are expecting an experience that has become that of legends.”


Legacy issues aside, the US concert biz is going through a crisis of festival overload which led to an overload of recent articles about the problem from Stereogum, USA Today, Chicago Tribune, Washington Post and elsewhere, making even a known-quantity like Woodstock who had been off the festival circuit for a decade a hard sell in a crowded market. As former festival Marketing Director Nicole Blonder sees it, “there’s definitely a glut of festivals, but overall ticket prices have gone up significantly, and the average person just can’t afford to go to as many shows.”

And since Woodstock 50 kept cutting it close with planning and locales, the organizers expected that going up to and past Labor Day, thousands of people in all the demographics would keep their summer plans open indefinitely in the hopes that the fest would happen. they expected that fans would be ready to shell out half-a-grand for a three-day pass and then also pay up for travel and lodging, likely putting the costs as over $1,000 per person. That’s a hell of a last-minute summer commitment.

Along with the issues of demographics, fest overload, and expectations, Woodstock 50 also didn’t think about what should have been an obvious connection for them. They could have hearkened back to the famed 1969 show with its political connections. But instead, they made a pretty timid effort outside of Lang name-checking a few topics in his March 2019 announcement. Lang and company did include the voter registration group HeadCount in their March announcement, but that was it and the non-profit only talked up Woodstock 50 in one press release which wisely focused more on Ariana Grande. From a marketing and socially responsible perspective, this was a big flub by Woodstock 50 considering how closely politics were tied to their first fest, especially centering around the Vietnam War.

Even without a war involving a draft now, there were plenty of other issues that W50 could have closely aligned themselves with including Black Lives Matter, environmental organizations to combat global warming, LBGT+ rights organizations, anti-gun violence groups, immigration rights advocates, #MeToo, pro-choice groups (NARAL). There would also be some challenging topics where the ground had shifting over the decades about where US culture stood, including drug legalization, the anti-war movement. And what about the hippie ideal of free love in a post-AIDS world? Even if you believe the myth that millennials don’t care about politics (tell that to the students who started Never Again), why ignore politics and not try to engage a younger generation, especially one that’s starting to get stirred by a GOP that scapegoats minorities? Much as later-day skeptics can laugh at the caricature of the burned-out hippy, their commitment to social activism (even if it was in their own self-interest) was something that Woodstock 50 could have and should have pushed.

But any kind of missed opportunity with political connections pales in comparison with Woodstock Enterprises’ mile-long list of screw-ups that they indulged in recently to sink their own 2019 festival. It’s tempting to think of some other half-baked plans they could have hatched this year to match their blunders. But you’d have to really work hard at that, say booking a minefield as a venue or rotating set times.

All of that would have been an improvement compared to what the Enterprises came up with though. Lang, alongside with Woodstock 50 LLC president Greg Peck, worked oft the 1969 playbook where they similarly had to scramble at the last minute to secure a venue and get all the necessary permits. Many of the news stories about Woodstock 50 pointed out the similarity as if to say ‘well, they pulled it off once, so maybe they can do it again.’ But this supposed strength that Lang and others had shown to turn the 1969 mess into magic turned out to be their greatest liability now where Woodstock Enterprises couldn’t get the stars to align with their plans. The seemingly endless saga of Woodstock 50 story might be seen as a testament to Lang and his partners’ ongoing determination. But it took so many disastrous turns that the story became a farce-comedy that didn’t know when it had played itself out.

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Read Part 1: Woodstock at 50: From Glorified Historic Disaster to Modern Day Joke

Read part 3: Woodstock 50’s Cautionary Example: Memories of a Cancelled Free Festival