In a clip from the documentary of Woodstock 1969, a newsman cautiously asks co-creator Michael Lang, "Are you going to do another one?"

"If it works," Mr. Lang replies, half-disbelieving that the near biblical conjoining of young people and music, if not the ecosystem of upstate New York, will all make it through the weekend.

An anomaly, the original Woodstock remains the quintessential case study in managing complete chaos and turning it into something beautiful. In decades since, festival business has become big business, with much more corporate oversight. And on the opposite end of the spectrum, the aborted Fyre Festival in the Bahamas earlier this spring was nothing more than a lesson in creating a disaster, promoted as partying with fashion models. It is now reportedly under criminal investigation.

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From a management point of view, what's more interesting are the lessons drawn from festivals that capture a bit of the grassroots, lightning-in-the-bottle spirit of Woodstock, and yet manage to continue year after year.

As Linda Tanaka, artistic managing director of the Vancouver Folk Festival, says, once her festival starts, it largely runs itself as teams of volunteers take over. "It's a huge relief when they do that. Everything that you worked on over the winter, all the parts are moving, and we can't stop it. It just keeps on going."

The Vancouver Folk Festival (running this year from July 13 to 16) follows an annual cycle that begins in the fall with a somewhat traditional arts-festival approach.

"We have different grants that we work on, different public funding that we have to apply to. Usually the end of September is the deadline for some of those things," she says. It's a cycle of reporting on last summer's event in order to get funding for the next festival, followed by putting in offers to musicians. In the winter, the festival has just three full-time organizers and two working part-time.

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Closer to the festival date, there is a clear delegation of functions: site manager, production manager, operations manager and so on. The latter, in particular has to deal with the hassles of politics or, specifically, permits from the city, which can be difficult given the festival's Jericho Beach Park location, adjacent to a residential neighbourhood.

An advantage, though, of organizing the same festival every year is that certain things don't have to be immediately solved but can evolve over time. For instance, the festival is no longer allowed to run big power cables across the parking lot. So next year, it plans to work with the city and parks board to develop a power kiosk on site, lowering its power bill.

That's the less glamorous side of festival management. In fact, most of it, from water problems to recycled plate programs, isn't glamorous. And even though the draws of the festival are the workshops in which performing musicians trade songs before their evening shows, "I don't get to see them. There's always something happening" that needs her attention, Ms. Tanaka says.

Shauna de Cartier similarly has myriad fires to put out, doubly so since she runs two festivals each summer: Edmonton's Interstellar Rodeo (July 21 to 23), which she started up in 2012, and since 2015, a Winnipeg edition (Aug. 18 to 20).

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For her, the annual festival cycle doesn't feel routine yet. "I think I'm more seasoned, but we're refining our systems constantly. It's always a new challenge. It feels anything but rote."

Her festivals differ from Vancouver's in that she doesn't depend on grants, and so instead of coming from an arts-funding culture, Interstellar Rodeo stems more from her experience running Six Shooter Records in Toronto and managing bands. However, the festivals are also run by volunteers.

"That was a challenge in recruitment, management, training and making sure all of our people are really happy and able to fulfill the responsibilities that we've given them. That was probably the highest learning curve for us," she says.

Unlike festivals with multiple stages, Interstellar Rodeo has only one, eliminating headaches such as the audio of one performance clashing with that of another. On the other hand, it makes choosing the running order of artists that much more important, given the more intimate feel Interstellar aims for, Ms. de Cartier says.

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It hints at a more centralized, personalized management arrangement, since the idea is to create her idea of a perfect festival: watching bands, sipping a glass of wine, etc. Listening to her describe her approach, it's a subtly different management style, aimed at creating a different festival experience.

The Blue Skies Music Festival in Clarendon, Ont., meanwhile, has been running each year for four-and-a-half decades largely on the enthusiastic labour of the attending audience, or at least around 100 of them. No organizer gets paid, making it far more the communal camping ideal than Woodstock could ever be.

"We've been sold out in advance for about 20 years," says Danny Sullivan, currently volunteering as artistic director. The property is also owned by the festival itself, which attracts between 2,000 and 2,500 attendees.

Each of the 100 or so in charge oversees a particular function. One person looks after sanitation, one looks after parking and so on. And each has an apprentice who takes over the job subsequently. "No one stays in the same position for more than three to five years. That keeps the thinking fresh and brings new ideas forward," Mr. Sullivan says.

"One of the weird things about the organization is that we decide everything by consensus, which means you have to talk 100 people into what it is you want to do, because any one of them can block the consensus. So, a lot of things change very, very slowly," he adds.

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Yet even with the free-spirit feel of Blue Skies, the running of the festival goes on all year, beginning with various meetings in the fall and a retreat in the winter for organizers. It creates a similar pattern as with other festivals, taking many months. Still, the hippy vibe, Mr. Sullivan acknowledges, "is a bit of a nostalgia trip."