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Portland’s Best Daycation is a Cheap Flight to Pendleton, Where the Cowboys Still Walk The Streets

In 50 minutes, you’re in a different world.

Pat Beard had a pitch for Fred and Carrie.

The former professional cowboy-turned-Pendleton ambassador wanted to invite Portlandia out to Pendleton, the Eastern Oregon city famous for its rodeo and tightly tied to the spirit of the Old West.

"I wrote to the producers of Portlandia and I said, 'Let's do an episode where they fall asleep and wake up here during the Pendleton Round-Up!" Beard says. "They wake up and they're like on a different planet."

Portlandia didn't bite, but you can live that very surreal experience on your own thanks to Boutique Air. It's kind of magical: An hour after leaving Portland, you land on a bluff overlooking the endless horizon of high desert.

Boutique Air—owned by Shawn Simpson, a former Google employee—exists only because of a federal subsidy program called Essential Air Service, rewarding airlines that reopen abandoned routes to isolated rural communities. And so for $59 one-way, we made the 200-plus-mile journey in a matter of minutes.

"If it weren't for EAS, the tickets would cost twice as much," says Steve Chrisman, a city employee whose grab bag of duties includes managing the airport. "The difference between Boutique and other EAS airlines is, the others tend to be focused on the bottom line. They try to run it like a normal commercial airline and make money by hammering business customers with fees. That doesn't work because you could always just drive. Boutique gets that and has made it really pleasant to fly."

It is the most hassle-free flight I've had since early September 2001. Boutique flies out of an office outside the main terminal at PDX. You can show up a half-hour before your flight, park for free and hop on without going through TSA screening. The plane is a Pilatus PC-12, a small, single-engine turboprop that holds eight plus the pilots.

In 50 minutes, you're in a different world.

You probably know that Pendleton is home to the famous woolen mills. It's also home to the Round-Up, a massive weeklong rodeo that draws 50,000 people, including every Oregon politician of note. Pendleton's rodeo grounds are the Fenway Park of the sport, a storied stadium famed for quirks and atmosphere.

"Around here, we base our calendar on Round-Up," he says. "It's like John Wayne meets Mardi Gras. The town shuts down for a week, and we have a party on the streets."

Thanks to that rodeo, Pendleton has a number of world-class makers, including the famous Hamley & Co., which custom-makes renowned rodeo saddles, and a hattery which uses blocks of wood from the 1800s to shape felt cowboy hats into the perfect fit.

Pendleton also offers tours of the underground catacombs that Chinese laborers built beneath the entire downtown, its tunnels servicing sheep-herder brothels on into the 1960s. Nearby, the Confederated Tribes of the Umatilla runs the state's largest casino and Tamástslikt Cultural Institute, a massive museum that covers the past 10,000 years of the tribe's history.

"I think some people in Portland would love to come out here on Boutique, order yourself a pair of custom-fit cowboy boots and a hat," says Beard. "We've got world-class makers out here. And more tourist destinations that most cities twice our size."

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