Let’s look at the 5 best stops in Pendleton, Oregon. It’s a mid-size town in the Northeast corner of the state. First of all, I may want to move here and let me tell you why. The weather is mild and dry, with 200+ days of sunshine yearly! 200+ days of sunshine. What’s not to love?! Of course, it’s about 3 1/4 hours from Portland, outside our desired settling-down-at-some-point range. But did I mention they get 200+ days of sunshine?

Noelle here, by the way.

Cool Facts About Pendleton, Oregon

Beside more than 200 annual sunny days, here are some city details.

• Population: 16,841 (2021)
• Umatilla County seat
• Oregon Trail stop
• Agricultural and ranching center, whose motto is “The Real West”
• Home to Pendleton Woolen Mills and Pendleton Roundup

Our Visit to Pendleton

We arrived on the last day of September; it was sunny and 75 degrees F. The Portland metro area held grey cloudy skies this morning, so we drove east toward the sun! We came to blue skies over Hood River and more blue all the way to Pendleton. Glorious! Our family and friends say it’s been the driest summer they can remember, but honestly, the rain came a few days after we got home and pretty much stayed until we drove away.

Our kids and grands are typical Pacific Northwest natives. We heard several of them exclaiming joy over the return of the rain. And I know it’s true because I also looked forward to the rain coming back. The rain and the beginning of the school year herald the new season. One I also used to wait anxiously for. But now, after traveling for a couple of years and being reminded of what sunshine is like, the gray skies of Portland and Seattle depress me.

So off we go to Pendleton along Interstate 84 as we go to Idaho to visit our daughter. As soon as we got to town, we got off the freeway and drove straight to the Pendleton Woolen Mill.

Pendleton Woolen Mill

1. of 5 Best stops in Pendleton, Oregon

The mill has been making woolen blankets since 1909 and is family owned/operated for more than six generations. Initially making blankets for the Nez Perce nation near Pendleton, they added men’s woolen shirts in 1924 and a womenswear line in 1949. During non-Covid times, visitors can tour the mill and see the blankets being made. We watched as best we could through large windows but only saw a couple of hanging blankets and pallets of yarn. Nevertheless, it was pretty neat, even though we couldn’t take a tour.

I fell in love with a beautiful Pendleton wool coat and promptly snapped a picture for our oldest daughter. She also loves the Pendleton woolen line. Well, once we got back to the camper and I began typing this, I looked it up to add a link in case you, dear reader, would like to gift me this jacket. Ha! It’s named Toboggan! Just like Steve’s trail name! So I should have it, but you know I’ll never spend $489. Not in this truck camper, semi-retired, no-income kind of life. We get to see a lot of cool stuff. But a $500 jacket is one of the cool things we take pictures of and leave on the rack.

Mom took us to the Pendleton Woolen Mill in Camas, Washington when I was a teenager. Back then, it was more of a mill that sold blankets, textiles, and fabrics. It was less of the clothing and accessories store that it now is. At least, that’s how I remember it anyway.

My sisters and I each got to choose fabric for a skirt, while Mom purchased fabric to make herself a jacket. I chose a tan and black plaid, which Mom lined with a silky material and crafted into a pencil skirt. I loved that skirt and remember feeling so stylish when I wore it. The Camas store and the Woolen Mill Store on SE McLoughlin in Portland are still there. So you can buy your fabric there to make your skirt!

2. Pendleton Underground Tours

The underground tour is the second item on my list of 5 best stops in Pendleton. Taking visitors through the area’s gritty history, this tour explains the gambling, bootlegging, opium dens, and the Chinese immigrants who lived in the rooms & tunnels beneath the city’s red light district in the late 1890s and early 1900s.

For only $15 each, the 90-minute tour is fun, and we highly recommend it. Our guide, Becky, was knowledgeable and made it a fun experience. The saloon was neat, and I’d love to return to it during one of their summer Saturday cocktail hours.

Above ground, we toured a brothel that had been boarded up in the 1950s and only recently re-opened. That was an exciting portion of the tour!

3. Oregon Grain Growers Brand Distillery

My 5 best stops in Pendleton would only be complete with some alcohol! So we stopped at the Oregon Grain Growers Brand Distillery and were not disappointed. This distillery is part of Pendleton’s Maker’s Tour, a 13-stop, four-mile walking tour of local artisans and, well, “makers.” From a Friday night Farmer’s Market to the Pendleton Center for the Arts, this Maker’s Tour is fantastic.

As the first distillery in town since Prohibition, Oregon Grain Growers Brand focuses on crafting quality spirits from locally grown grains and produce. We stopped in for a tasting and tour. We ate lunch, tasted some alcohol, and forgot to ask about a tour. Maybe another time?!

I’m a gin lover, while Steve is more of a bourbon guy. However, I was still super excited to try the Pic-Nic Watermelon Vodka. This vodka delivers a good flavor by utilizing watermelons from the Walchli Farms in nearby Hermiston, Oregon. In case you don’t know, Hermiston, Oregon, grows the best watermelons EVER! I mean, EVER. So try one. Or if you can’t, just order some of this vodka yourself!

Their 1953 Seeburg Selectomatic Jukebox inspires Oregon Grain Growers Brand Deluxe Gin. Distillers tested over a hundred variations of botanicals when crafting this gin. There are also 100 music selections in their jukebox. Coincidence? I think not. In 2019, this yummy goodness won a gold medal in the Classic Gin Category of the American Distillers Institute’s Craft Spirits competition. It smelled divine and tasted pretty good too.

We got a little surprise from the Horsepower Horseradish Vodka. Now that was delicious! Steve had a Bloody Mary made with it, and it more than delivered! We liked it so much we bought two bottles to go! One for us and one for our daughter (we may have helped her drink a good portion of her bottle 🤣). Yep, I’ve got a little horseradish vodka crush going on here!

Anyway, we enjoyed a delicious meal and even better cocktails before continuing our tour of Pendleton. Steve’s been craving a good hamburger all summer while he was hiking. So he was excited to finally get THE burger that hit the spot!

4. Pendleton Hats, Saddles & Wild West Gear

Multiple Stops on the top 5 best spots in Pendleton

Pendleton Hat Co.

Here are another couple of stops on the Maker’s Tour that make my 5 best spots in Pendleton list. First, the Pendleton Hat Co. makes beaver and rabbit fur felt hats! What else is there to say? Perk Perkins has owned Pendleton Hat Co. for many years and was busily re-stretching a hat for a cowboy while we watched.

In addition to selling new & refurbished hats and accessories, Perk will also clean and restore hats brought in to him. He cleans them while retaining the “style” and “flavor” they’ve accrued over years of being well-loved. Only a true hat-lover can appreciate the need to maintain the style while cleaning and restoring.

I’ve never seen so many cowboy hats as we saw in this store. What a fun stop on our tour.

Hamley Western Store & Saddle Shop

Hamley & Co. owns a renowned saddle company, the Slickfork Saloon, a cafe, and a steakhouse. This is a walk into the Old West. The Saddle shop has been crafting legendary saddles since 1905, right here in this same building. It’s certainly a site to see. If you’re in Pendleton, you’ve got to stop in here for an authentic taste of Old West gear!

J.J. Hamley helped organize the first Pendleton Round-up, and the company has provided hundreds of trophy saddles for it. 58 World Champions have ridden with Hamley Saddles. There’s a lot of history here! Plus, you can get a great bite to eat too. What’s not to love about this stop?

Staplemans Boots & Leather

This shop is not so much a storefront but more of a traditional boot-making shop. There’s a tiny area at the front with different colored leather pieces, then an ample counter. Behind it is a large open workspace with two boot makers.

I met Richard, who owns the shop and has been making cowboy boots since 1999. His assistant is younger and recently moved to Pendleton from the East Coast (via Portland). I chatted with them for a few minutes while admiring their skill. Every single pair of boots and shoes are made by hand. By hand. Who does that? It was fantastic to watch them for a few minutes. There were hundreds of shoe molds (is that what they’re called) on shelves around the shop, and both shoemakers were stretching leather around a mold.

It was fun to stop in here and chat with the artists. I’ve always been interested in leatherwork, so seeing them in action was a treat.

5. Pendleton Round-up

No 5 best spots in Pendleton list would be complete without mentioning the Pendleton Round-up. I’ve only been to this rodeo once as a teen, and my most significant memory is of a ridiculous allergic reaction to all the hay and animals. I was sneezing, and my eyes swelled, and I honestly don’t remember anything about the rodeo itself, only the severity of my allergies. However, everyone in the Pacific Northwest knows that the Pendleton Round-up is the place to go for rodeos.

It’s a week-long affair every September, with this year completing the 111th year of rodeos. In addition to daily rodeo shows, there are parades, Western shows, concerts, and tens of thousands of cowboys and cowgirls (even ones from the city, ha!).

The Pendleton Round-up’s website says the Happy Canyon Night Show “is a show depicting the settling of the American West, beginning with a portrayal of the Native American way of life before the arrival of the white man, continuing with the arrival of Lewis and Clark, followed by the prairie schooners of the pioneers of the Oregon Trail and concluding with a reenactment of a frontier town’s rollicking main street mishaps.

The colorful pageant takes you into the past to relive the experiences of our forefathers. The show begins with the portrayal of the early American Indian culture. Emigrants, seeking a new life, come to the frontier and soon the two cultures clash. Fighting breaks out, then peace comes and the scene changes to that of a wild frontier town. The show ends with a patriotic flourish that is unique and not seen anywhere else. Don’t miss the retelling of the story of the “Old West” in a way that you will not soon forget!”

Maybe we need to come back next September to check out the rodeo, the shows and all the fun that surrounds it!

Other cool things in Pendleton, Oregon

Charm Trail

Like Nevada’s loneliest highway in America, where I collected stamps in small towns, Pendleton has a Charm Trail. Buy a $6 bracelet at one of several “trailheads,” then “hike” around town to various stores, museums, and eateries to purchase add-on charms for $1.50 each. It’s a great marketing campaign encouraging visitors to travel around town and see more of Pendleton’s “charm.” Even the KOA where we stayed has its own tiny coffee pot charm. This is a great idea, and I was sorely tempted…just for the thrill of the hunt.

Pendleton Book Store

Steve and I stop at bookstores in almost every town we visit. We love supporting local book lovers and appreciate this store’s thoughtful and neat layout.

Used books are half their new price with a couple of bonus carts of 25 and 50-cent books. I picked up three new to me paperbacks for $1. You just can’t beat that price. It’s a great store, so stop in if you’re in town!

Downtown Wild West Saturdays

On Saturdays from June through September, visitors and townspeople can enjoy free, family-friendly Native American and Western shows at 4:00 and 5:00 pm. The location changes weekly depending on which city block is closed for the events. There’s even a speakeasy at the Pendleton Underground Tours! From 4-7 pm, the over-21 crowd can go to the Shamrock Cardroom and Saloon for cocktails.

Downtown horseback rides and Old West Wagon rides are available through music-filled streets. It’s too bad we were too late for all the fun this year, but I’d love to return next year!

Make your way to Pendleton, Oregon

Well, I sure hope you’ve enjoyed my 5 best stops in Pendleton tour and that I’ve inspired you to visit. Of course, I didn’t mention all the wonderful nature surrounding the city, but besides the KOA, we enjoyed boondocking out of town near the Snake River. Thanks for stopping by!