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.

(Martin Cizmar)

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."

Best of Portland 2017

This Year, More Than Ever, It's Important to Stop and Take Note of Everything That Makes Portland What It Is

Here are the Winners of the Best of Portland Readers' Poll 2017

Here are the Things WW Declared "The Best" in the Last 12 Months

Inside Mall 205, You'll Find Oregon's Last Remaining Magic Shop

Portland's Raging Grannies Have Been Protesting Since the 1960s, And You Do Not Want to Mess With Them

A Vancouver Man Bought Naked Falls Swimming Hole, So He Could Re-Open It to the Public

Rodney Scott Puts On Portland's Greatest Indie Firework Show

Cabel Sasser Found a McDonalds Mural That Led Him to Uncover a Secret Collection of Art

Two College Students Started An Organization to Provide Bras and Underwear to Homeless Women

Jim Hipsher Is Portland's Greatest Live Book of Poetry

These Two Women Make Showing Up for Jury Duty A Lot Less Terrible

On Northeast Broadway, You Can Learn Boxing From Two-Time World Champ Molly "Fearless" McConnell

Portland Urban Golf Makes the Entire Changing City Its Ever-Evolving Personal Golf Course

Did You Know You Can Play a 9-Hole Portland-Themed Mini-Golf Course?

Seven Years Ago, New Trail Blazer Caleb Swanigan Was 360 Pounds and Living in Homeless Shelters

Each Week, a Group Goes to Laurelhurst Park to Throw Axes Through the Air—And They're Really Good

Portland Now Has a Nonprofit That Gives Kids Access to Free Pinball

Marathon Taverna Hosts Portland's Best Late-Night Raffle, Giving Away T-Shirts and 100-Level Blazers Tickets

The City of Portland Made a Sign Reading "Heartbreak Dead Ahead"

There's a Secret, Profit-Free Bookstore "Forest" on Division Street

You Can Get a Pre-Addressed Letter to Trump from Paymaster Lounge's Vending Machine

A Local Business Totally Trolled Willamette Week—And It Was Awesome

The ACLU of Oregon Has Emerged as Portland's Most Consistent Free-Speech Fundamentalists

Division Street's Oregon Theater Is Portland's Greatest NSFW Twitter Account

There's a Library in Vancouver Full of Hundreds of Books That Have Never Been Published, And Never Will Be

Alberta Street's American Legion Post 134 Went Rogue—Inviting Homeless In and Hosting LGBTQ Nights

Beaverton's Spectra Gymnastics Provides Play Spaces for Kids on the Autism Spectrum

There's a Hidden, Underground Sculpture Inside the Standard Insurance Center in Downtown Portland

One of the Oldest Retail Businesses in the City is a 127-Year-Old Woman-Owned Costume Shop—Now, It's in Danger of Closing

In the Portland Area's Wealthiest Neighborhood Lies a Hidden, Public Scottish Garden As Large as the Japanese Garden

The Zymoglyphic Museum is a Self-Contained World of Rogue Taxidermy and Steampunk

Every Sunday, Portland Hosts a Real-Life "Fast and the Furious"

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

Oregon City's Tim Kovar Is one of the Nation's Foremost Tree-Climbing Experts

Hero Punk Stole the Satyricon Sign and Sold it to VooDoo Doughnut Owner in Exchange for Lifetime Doughnuts

High School Junior Won a Major Science Competition in the World By Investigating Where Portland's Fish Went

Who Do You Call When Your Goat Is Throwing Up? Portland's Go-To Goat Doctor, Of Course

Meet the Portland Poodle Who Dresses Better Than You

Every Saturday, A Train Runs Through Oaks Bottom, Making Birdwatching Actually Fun

Right Now, Three Dogs Living at a Southeast Portland Dispensary Are High on CBD Dog Treats

Feeling Sad Lately? Snuggle Up to One of Portland's Therapy Bunnies

Pet Barn Will Watch Your Boa Constrictor While You're Out of Town, But Not Your Dog

In the '90s, Two Portland Teenagers Aired Old WWF Matches. Now, They Have a Treasure Trove of Wrestling Archives

Portland Science Rapper Coma Niddy Has the Best Rhymes About Black Holes You've Ever Heard

There is a Secret Willamette River Bridge Most Portlanders Have Forgotten Exists

Hero Portland Man Built an 8-Foot Tall Multnomah Falls Out of LEGOs

There's An Alley in North Portland Where Robots Will Call Out To You

Daddy Mojo's Has the Finest Gallery of Signed Celebrity Memorabilia of Any Bar in Portland

Portland's Black Book Guitars Owner Has Tracked Down Guitars from Elliot Smith and Kurt Cobain

Thank God for the Los Cactus Food Cart, Which, For 14 Years Has Fed Junkyard Customers for Cheap

Two Portlanders Created a Willy Wonka-Style Edible Forest Near Milwaukie

Portland's Best Bagelmaker Was Saved By Someone in Line at WinCo—Now, He's Repaying Strangers' Kindness

You and Your Friends Can Drink for Free for an Hour on Your Birthday at This Portland Bar

The Portland-Area Finally Has Hong Kong-Style Ice Cream Bubble Waffles

Yes, There Is a Place in Portland Where You Can Try Witches' Brews and Heal Yourself with a Fire Pit

Portland's Best Fritters Come From Donut Queen on 58th and East Burnside

When a Pro-Trump Rally Came to Portland, a Good Samaritan Helped Calm the Tension By Handing Out Free Weed

If You Haven't Noticed Yet, the Trail Blazers Twitter Account is on Fire

The New Market of Choice On Belmont Has The Very Best Grocery Store Beer Selections We've Ever Seen

Yes, There a Secret Underground Bowling Alley in the Center of Portland

When Portland Saw Snowstorms, the National Weather Service Twitter Became Our 24/7 Therapist

Willamette Week’s reporting has concrete impacts that change laws, force action from civic leaders, and drive compromised politicians from public office. Support WW's journalism today.