“The thing I love most about the Fair,” says Charlie Ruff, Oregon Country Fair’s outgoing general manager “is that, at its best, as a community, people can come and be themselves — they can express themselves in an environment as free from judgment as you’ll find.”

Ruff steps down later this summer after 12 years on staff, the last seven of which he served as GM. He will remain, for the time being, a Fair volunteer. Ruff’s replacement is Tom Gannon, a longtime Seattle resident who recently relocated to the area.

We caught up with Ruff as busy crews prepared for this year’s OCF.

In June at the OCF site near Veneta, the woods are still lush and verdant and construction is in full swing. “The reality is, everything happens all at once,” Ruff says. “By now, we’ve moved our office on-site, and we’re there 24-7.”

Ruff stewards an interconnected web of 65 operational crews.

“We have to be there to make sure they get what they need,” Ruff says, “to build this small city in a flood plain.”

Approximately 45,000 visitors come to Fair each year. Saturday is traditionally the busiest day, with 18,000 tickets sold.

Now in its 46th year, OCF is more than just tradition, Ruff says. “The Fair itself is a multi-faceted, complex organism, and this organism has yearnings of its own that bubble up from inside,” he explains. “The job of the manager is to help manifest that desire, to make those wishes come true.”

During the event itself, Ruff works with “several thousand volunteers, several thousand booth folks and a couple thousand entertainers,” he says, adding with a laugh, “I get very little sleep during the Fair.

“The hardest thing about the Fair, from a leadership perspective, is that everybody thinks you have all this power,” Ruff says. “But that power is disproportionate to reality, because there are so many stakeholders and communities represented.”

Ruff says that he’s tried to balance his focus between the OCF’s relationship to the outside world — i.e., its philanthropic efforts as a nonprofit organization — and the event itself. “We’ve built a good platform for fundraising,” he says, noting that during his stint as general manager, he’s seen an uptick in the culture of giving amongst the Fair family.

How do you preserve what’s special and still look to the future?

“As the Fair becomes more of an established entity, it’s hard to put limits on growth,” Ruff says. But it’s essential for the OCF’s future, he says, “that we focus on managed and planned growth.”

A longtime OCF volunteer prior to taking the GM position, Ruff recalls challenges during his tenure. “In a community built on tolerance and freedom of expression, there are always a few outliers, people who are struggling,” Ruff says.

Still, OCF staff and volunteers are trained to approach thorny interpersonal dynamics with empathy and compassion, diffusing tensions before they escalate.

Occasionally, weather does pose a palpable challenge, as with the great deluge of 2009, when a major rainstorm turned the 280-acre site into an almost impassible mud pit. “It was the most rain that fell on that calendar day in the history of Oregon,” Ruff says. “That was very hard.”

He’s also been a witness to tragedy. “Then there was the plane crash. We lost some volunteers,” Ruff says quietly, referring to a 2012 accident off-site in Veneta that claimed four lives just weeks before the Fair opened. “You have to deal with it, but you grow through it.”

Challenges can also bring about transformation, Ruff adds, like the year when the Federal Transit Authority changed its regulations about shuttle service. When bus rides to and from the Fair were threatened, Ruff was able to negotiate a positive long-term solution by having the OCF simply purchase LTD’s regular service routes — all routes for any rider on the LTD system  — during the three days of the Fair.

“It was a way to say thank you to the community,” Ruff says of the transportation solution. “And we could not be prouder of what we’ve negotiated.”

Embarking on his last season as general manager, Ruff will train incoming GM Tom Cannon throughout the summer, ensuring a smooth transition for the new leader and the organization as a whole.

Ruff offers parting advice to novice Fair-goers. “I’d suggest that they bring an open mind. And I’d suggest that they bring an open heart,” he says. “And I’d suggest that they take the bus.”

He continues: “Don’t spend too much time planning how you’re going to do the Fair, what you’re going to see and when it happens. Come, throw yourself in the river and see where it takes you,” Ruff advises.

“Let go,” he adds, a fitting swan song. “You will find magic, and it will find you.”