Zack's Rating: ★★★★★ Ease of Travel: ★★★½☆ Wallet Friendly: ★★★★☆
Tackle your bucket list items now. Nobody knows how big their bucket is…
— ZW
Pendleton, Oregon is our kind of place. The moment you get there and the name and history starts following you around. The town is Pendleton. The mill is Pendleton. We ate Pendleton beef and we drank Pendleton whisky. Somewhere along the line that name turned into a marketing heavyweight for quality goods, and by the end of the week it was stamped on just about everything we touched.
For us it carried a second meaning. Pendleton Woolen Mills has a mill in that town, and Pendleton is one of the cornerstone suppliers on our floor and so much of what we stand for: real heritage, American craftsmanship, and a company that lifts up both the local community and the Native community it has traded with for well over a century. We went for a rodeo. We came home understanding our own shelves better.
Hats Worn:
I rode this trip with two on rotation: a Resistol 30X and the Stetson Llano in chocolate. The Llano did most of the heavy lifting — it photographs well, it handles a long day in the sun and the dust, and chocolate hides a rodeo grounds better than anything lighter.
Natalie wore the Stetson Broken Bow, which is known for its Gus crown — the forward-sloping, tall-backed shape that reads as old-line western the second somebody walks in with it. She layered Pendleton scarves and accessories on top of it all week, which felt right in the town where the wool comes from.
Moon Ridge Reflections:
This was one of our favorite domestic trips we have ever taken. We spent a week learning more about our own suppliers, swapping stories with other hatters, standing in an arena unlike any other in the sport, and doing all of it in a fun little party town tucked into northeastern Oregon. There is something clarifying about visiting the place a product actually comes from. You stop selling a brand and start telling the truth about it.
Getting There:
Pendleton is not easy to get to, and that is part of its charm. There is a small commuter airline called Boutique Air that flies straight in. I used to fly Boutique back to Carlsbad, New Mexico in my oil and gas days, so I know exactly what you are getting — eight to ten seats in a converted prop plane built for small-market service. I never had a problem with them. For this trip the availability and the schedule just did not line up with ours.
Instead we flew into Pasco, the Tri-Cities airport, which sits about an hour and twenty minutes from Pendleton. United did a good job overall, though we took two connections on the way out to make our schedule work, and we will say it plainly: the short connection times they sell you out of SFO are insane. Build more cushion than the app tells you to.
We rented from Alamo in Pasco. There was a twenty-minute wait for a car, and no harm done, because the staff had such good attitudes about it that the wait stopped mattering. The drive from Pasco is easy and uneventful — pretty, rolling hills, not much else to look at. It does hold one of the eating highlights of the whole week, which is where this trip really started.
STANFIELD — THE FIRST STOP
Where We Ate:
Broken Barrel — ★★★★★. We took a side mission on the drive in and stopped here, and after a full day of running through airports with no time to eat, it was exactly the right call. If you know the reference — and Crawford certainly does — this place has Luke's Diner energy. Our bartender Jason made an outstanding Bloody Mary garnished with a mozzarella stick and a chicken slider, which is either genius or madness and we have decided it is genius. Natalie had an excellent chef salad. Ten out of ten, and we knew right then the week was going to be good.
PENDLETON
Where We Stayed:
Red Lion, Pendleton — ★★¼☆☆ (2.3). A clean two-star property, and we mean that as information rather than an insult. Think Days Inn or Comfort Inn. It sits about two miles from the Round-Up grounds, straight up a hill, so walking is off the table, but they run a shuttle to the grounds and we used it happily. Here is the honest version: know what you are booking, and you will enjoy it fine. We did.
The bonus nobody tells you about is the view off the back side of the property, which is genuinely breathtaking. That alone bought back a lot of goodwill.
One real tip, learned the hard way. This was a fairly spur-of-the-moment trip, and planning our lodging further ahead would have opened up more options. It also would have cost more. That is the trade, and it is worth deciding which side of it you want to be on before Round-Up week gets close.
The Bulls:
Our first night we went to the Xtreme Bulls finals at the Happy Canyon arena, and this is a do-not-miss event. That arena is one of the best bull riding setups we have seen. We have not seen a hundred of them, so take the comparison for what it is worth — but you can tell when a place is built right, and that one is.
The Round-Up Itself:
The Pendleton Round-Up — ★★★★★. The Round-Up is unlike any rodeo we have ever attended, and the reason is the ground itself. The arena is grass, with a dirt track running around it. No other rodeo on the circuit looks like that, and it changes everything about what the competition asks of a cowboy. The grass is slick, and these horses and riders are not running on it week in and week out. Nothing is routine here. This is real cowboy work, and the reason winners at Pendleton carry the respect they do across the western world is that they genuinely earned it on footing nobody had dialed in.
That dirt track around the outside is not decoration either. It is where the Indian Relay races run, and they are worth the ticket by themselves. Each jockey rides three horses, bareback, without stirrups. They come around, vault off at a dead run, take a few steps and leap onto the next horse while a catcher grabs the incoming animal and a holder steadies the next one. Those horses hit the exchange around thirty-five miles an hour. People who follow the sport call it the original extreme sport, and after watching it we are not going to argue.
The history runs as deep as the rodeo does. A half-mile Indian Race appears in the very first Round-Up program in 1910, and the relay format took shape in 1913. It has been part of this thing almost from the beginning. One more detail worth knowing before you pick your spot: the horses run the track, but every so often one takes an abrupt left onto the infield and jumps the low fence, which scatters everybody standing nearby in a hurry.
Pendleton Woolen Mills:
The mill tour and store — ★★★★½. We took the tour as authorized dealers, and it was the piece of this trip we keep coming back to. The part that stopped us was the dyeing. Pendleton dyes with a rigor that explains the thing our customers actually experience years later — a Pendleton blanket that still looks like itself decades on, colors that have not gone chalky or muddy the way lesser goods do. We have said "the color lasts" on our own floor plenty of times. Now we have watched why.
The half star comes off for one reason only: the tour was great and it was too short. That is the best complaint a person can have.
One note to keep straight, because most people do not. Pendleton Woolen Mills, Pendleton Whisky, and the Pendleton Round-Up Association are three separate organizations that happen to share a name and a town. The wool is the mill. The whisky comes from a different company entirely. The rodeo is its own association, and has been since 1910.
Where We Ate:
Mac's Bar & Grill — ★★★★. We started our first night in Pendleton sitting at the bar at Mac's. The room was packed with rodeo people and the atmosphere was lively from the minute we sat down. We ordered the prime rib, and it held up against most. I will own my bias here: prime rib is a cut you should not be able to ruin, so what I am really judging is whether the kitchen makes a good horseradish sauce. Mac's made a good one, so I will call it a good prime rib.
As happens on so many of our trips, the people took Mac's over the top. We sat down next to Keith and Becky, a couple from Corvallis, Oregon, out on a birthday trip of their own. We enjoyed getting to know them and found the same streak we look for in ourselves — they love to get out and see the world. Our server Claire made the whole evening, so if you end up at that bar, tell her we said hello.
Hamley Steakhouse & Saloon — ★★★¼. The atmosphere here is very neat and worth experiencing, and we suspect that on a week that is not Round-Up week, the food is better than what we got. Volume does things to a kitchen. We would go back on a normal weekend before we would write it off.
Virgil's at Cimmiyotti's — ★★★½. Steakhouses are hard to rate honestly, and they were running an abbreviated menu that week. Here is the fair way to put it: if you are calling The Palm a five, this is a good upper-mid-grade steak, and it is not trying to be anything else. The ambience is a solid 4.5 out of 5, and they did a great job running a packed room through quickly, which during Round-Up week is its own skill.
The Dough Cookie Co — one great cookie. That is the entire review and it is all you need.
Where We Drank:
Mi Tributo — ★★★★½. This one stayed with me, and it is the best small story of the week.
Mi Tributo was not even open the normal way during Round-Up. The man running it had set up a margarita bar serving straight out to the street, and he called us over for a huckleberry margarita. We asked if they opened later. He said no — too wild around here these few days, and he did not want them trashing his bar.
That made us curious, so we peeked inside. It is an incredibly intricate Día de los Muertos room: sugar skulls everywhere, paintings of women in the same motif, a little graveyard with wooden markers above the bar. The whole place is a tribute to the owner's ancestors, which is where the name comes from. Mi Tributo means "my tribute."
We wish we could have seen it running. Here is what stuck with us instead. A man built a room to honor the people he came from, and during the biggest money week his town has all year he kept the doors shut rather than let a rowdy crowd tear it up — then came out to the sidewalk anyway to make strangers a good drink. We ought to all be so steady.
Great Pacific — ★★★★½. We walked into this place late one night, and it told us early on that Pendleton was a town we were going to like. They had an outstanding classic country quartet playing early fifties and sixties tunes, with a crooner-type singer on the mic. It was an elevated experience, and we could have sat there all night.
The Pendleton Rainbow — ★★★★. A great dive bar. This is a Pendleton classic, and it gets rowdy on Round-Up nights. We went mid-day for some fries and an RBV, and the menu is perfectly small and simple. This place has the true feel of Pendleton.
Prodigal Son Brewery — ★★★¾. A decent little brewery with a true Oregon craft beer feel to it. Could have been my own poor choice, but we had the Huckleberry Wheat and it came out a little bitter. We would give this place another shot.
The Shops — and the People In Them:
Shops are full of stuff. What makes a shop is the people. We want to give two local businesses five stars here, and neither one earned it by what was on the shelf.
Before we get to them, a word about our trade. The hat business is a strange one. Seventy-five percent of the people we have met in it are some of the most supportive, kind, generous people you will ever come across — a genuine brotherhood and sisterhood that shares openly and pulls for each other. The other twenty-five percent have confused owning a hat shop with being knighted.
Pendleton Hat Company — ★★★★★. These folks are the very best version of that first group. It was an extremely busy week, and they unlocked their door, brought us in, and walked us through every area of the shop. Then they stood and talked with us right up until our dinner reservation. That is not customer service. That is the spirit of fellow purveyors of a specialized craft, and you feel it immediately.
Their shop is amazing on its own merits — one of the best collections of 100% fur hats you will find anywhere. They are an inspiration for hatters everywhere, and we left better at our own jobs for having stood in their shop.
Stapleman's Boots — ★★★★★. This one is not about boots at all. It is about being kind to another human being.
Natalie walked in and asked about the leather on a pair of Lucchese boots my grandfather, Dr. Eldon Pence, left to me. They are from the 1970s at the very least. Beautiful crocodile bellies that had started to show a few cracks in the leather. Mr. Stapleman took them, grabbed some conditioner, worked the repair, handed them back and told me I had at least another five good years in them. I tried to pay him. He refused.
I walked out feeling great, looking great, and carrying a large amount of respect for the man. If you are in Pendleton, go see him.
Additional Notes & Travel Tips:
Book lodging early or accept the trade. Round-Up week fills the town. Planning further out gets you more options at a higher price; waiting gets you fewer options at a lower one. Neither is wrong, but decide on purpose rather than by accident.
Fly into Pasco unless Boutique Air's schedule fits yours. The Tri-Cities airport is an hour and twenty minutes out and gives you a real rental car market. Boutique flies straight in and is a perfectly good little airline, so check their schedule first — if it works, take it.
Do not trust a short connection through SFO. That is the whole tip.
Rent a car. Pendleton is walkable in its core, but your hotel probably is not, and the drive in is part of the trip.
Go to the Xtreme Bulls, not just the Round-Up. Two different events, two different arenas, and the bulls are worth their own night.
Eat off Round-Up week if you can judge the restaurants fairly. Every kitchen in town is running at capacity during the rodeo. Our ratings above account for that, and you should too.
Final Thoughts:
This whole experience was amazing, and it lands near the top of every domestic trip we have taken. Part of that is the Round-Up itself, which is genuinely unlike anything else in the sport. Part of it is the bulls, and that atmosphere. Most of it, though, is the people.
Natalie picked this trip, which I should have expected. She has a way of choosing the thing that turns out to matter. What started as a birthday surprise became a week of learning more about the suppliers whose names sit on our shelves, and of swapping stories with other people who do what we do for a living. There is a particular kind of fellowship in that. You meet somebody who has spent as many hours shaping felt as you have and the conversation starts about three levels deeper than usual.
Then there is Mr. Stapleman, who will never know what he did. My grandfather's boots are wearable for another five years because a man in Pendleton, Oregon decided a stranger's family heirloom was worth twenty minutes and some conditioner, and then would not take money for it. I have been in business a long time. That is the whole thing, right there.
If a trip like this sounds better than what the guidebooks are selling, that is kind of our thing. You can read the rest of our trips over on Moon Ridge Travel. We plan journeys the way we take them — real tips, real people, and nothing straight out of a brochure. We also keep the hat side running back home, so if you want the trip and the hat to go with it, we can handle both.
Adventure with us, one destination at a time. For more information, email zack@moonridgecompany.com.