Have you ever heard of Pendleton, Oregon? If so, probably in the context of rodeo, wool, and whiskey – Pendleton’s legacies. When exploring Pendleton, you could definitely say it’s where the West is still wild. The town in Eastern Oregon tells the stories of adventure seekers and pioneers and for sure is one of the last bastions of America’s Wild West. But what is there to do, you might wonder?

I’ve come through Pendleton once before, on a road trip through Eastern Oregon. But eventually, I this time I stayed for 2 days to experience the town and the Pendleton Whisky Music Festival together with my friend Vanessa. We stayed at Motolodge Pendleton, feasted ourselves through town, and discovered some really surprising treasures.

In this article, you will find tips for traveling to Pendleton, Oregon. It turned out a little longer than initially planned. I was as surprised and enthusiastic when experiencing what the city has to offer, especially when it comes to arts and craftsmanship.

Disclaimer: This blog post is the result of a collaboration with Travel Pendleton who invited us for the weekend to experience Pendleton & the Pendleton Whisky Music Festival. However, this is an honest review of activities and eateries we tried ourselves. As everywhere on this blog, I only share things I absolutely recommend and think my readers will also love!

Where is Pendleton, Oregon located?

The city of Pendleton is nestled in Eastern Oregon’s rugged country in Umatilla County.

Getting to Pendleton

From Portland, it’s a 200 mi (320 km) long drive via I-84 through Columbia River Gorge and takes about 3 to 3.5 hours, depending on traffic.

If you prefer a faster way, I can recommend flying in with Boutique Air and arriving at Pendleton in style. The flight only takes an hour and you get great views of the Columbia River Gorge, Mt. Hood National Forest, and the rolling hills of Eastern Oregon on the way. Not to mention the views of the Cascade peaks – I’d say, flying into Pendleton is worth it for these already.

In addition, flying with Boutique Air is super smooth. Their terminal in Portland can easily be reached, with no lines for baggage, personal service, and almost no wait times as they fly with small planes, and handling is so much faster compared to big airlines. If you arrive by car, they offer free parking at their lot, which is super convenient.

Things to do in Pendleton, Oregon

If not the city yet, then for sure the name Pendleton rings a bell as you probably have heard of the brand Pendleton Woolen Mills. Besides Pendleton Whisky, this is the most famous and popular brand with roots in Eastern Oregon. However, Pendleton is well-known for its craftsmanship and as a reputational rodeo city, this is the best place in Oregon if you are looking for handmade leather goods, cowboy boots, and hats. So my first recommendation of things to do in Pendleton is:

#1 Stroll around town on the Maker’s Trail

When in Pendleton you shouldn’t miss to stop by local makers. I mean the original ones. Pendleton has a well-deserved reputation as a town where the best of Western Tradition & heritage lives on.

Pendleton makers were settled in Eastern Oregon long before vintage shopping and artisan-driven businesses were cool. The best part: in Pendleton, you can follow the local makers through town by exploring Pendleton’s Maker’s Trail.

By following Pendleton’s Maker’s Trail you can explore the craftsmanship of the Pendleton Community and get in contact with the local makers. It showcases Pendleton locals’ crafted mentality from saddles to boots, hats, wool clothing, and blankets, and opens the doors to artisans who are dedicated to traditional handmade historical Western items. Make sure to visit:

Pendleton Hat Company

Perk Perkins is not only the owner of the Pendleton Hat Company, but premier hatter in Pendleton. With his deft handwork and steamer, he can tip a brim and crease a crown to suit any taste and match any head.

He started the trade by refurbishing and selling used hats – these days most are new. When stepping into the store, you will be overwhelmed by the broad selection of manufactured hats lining the walls, from straw to leather. Perkins also creates his own designs from a beaver or rabbit fur blend.

Prizes for a hand-made and customized hat range between $200 and $2.500.

Staplemans Custom Boot Shop

If you are looking for a pair of handmade, customized boots, Stapleman Custom Boot Shop is your address! Richard Stapleman stands for quality craftsmanship and hosts four artisans that make and repair custom leather goods.

At Stapleman you can order boots, shoes, belts, bags, and more made to your specification. This Pendleton-Round-Up edition definitely is a special one.

Hamley’s Western Store & Saddle

Est. 1883, Hamley’s is the oldest western store and saddle shop in town. J.J. and Henry Hamley, sons of the original craftsman, continued the tradition of making legendary saddles, including their own innovative designs and custom work. Until today they sell fine western wear, jewelry, custom saddles, boots, and more. We couldn’t say no to getting dressed here in modern Western style.

Hamley’s & Co definitely is an institution in town and you’ll see the name Hamley’s on several signs throughout town: There is Hamley’s Steakhouse & Saloon, as well as Hamley’s Café and Wine Bar. Find more details on these eateries in the section „Where to eat in Pendleton“.

Pendleton Woolen Mill

No visit to Pendleton is complete without a stop at the OG location of Pendleton Woolen Mills, that’s for sure. If you’ve heard „Pendleton“, probably because of the Woolen Mill, Pendleton’s industry with international recognition. Pendleton Woolen Mills is the only remaining textile mill in Oregon and one of the largest blanket manufacturers in the country.

Until today, Pendleton Woolen Mills crafts high-quality wool clothing & blankets with enduring designs. The colorful and original, 160 years old patterns are still Pendleton’s most iconic items. The Pendleton Mill outlet store offers a broad selection of Pendleton blankets, clothing, and accessories, and hosts the largest selection of Jacquard blankets & wool fabrics, and remnants.

A small museum is also on site and free tours are offered four times daily during the week. If you enter these doors, you will not leave them with empty hands…

#2 Support local businesses

Take home a very special souvenir of a work of art made by an Eastern Oregon resident.

“A Piece of Pendleton” is a great store to do so. Owned and operated by the non-profit Pendleton Underground Tours, they sell locally made items and products representing Pendleton. In addition, they offer space for local artists and businesses to sell their locally-made products.

#3 Shop antiques & vintage finds

Community Thrift Shop and Reride Western Resale are great addresses. Here you can find vintage, Western & Native American clothing and accessories as well as pre-owned current styles.

Prizes are pretty fair. You might find a treasure to take home with you.

#4 Visit Pendleton Center for the Arts

Would you have expected a modern art center in Pendleton after reading this far? I haven’t! But got positively surprised by the Pendleton Center for the Arts. The space celebrates creative expression and community connection through experiences, education, and advocacy in the arts. It hosts a range of contemporary exhibits, wearable and functional fine crafts, and literary arts and music events.

Pendleton Center for the Arts is located in a historical building, the beautifully restored 1916 Carnegie Library overlooking the Umatilla River. It hosts a shop where you can encounter unexpected treasures that make great gifts and souvenirs: Jewelry, textiles, ceramics, art glass, and hand-printed cards by more than 80 artists.

The best part: Admission is FREE for everyone.

#5 Go on a Pendleton Underground Tour

A great way to explore Pendleton’s infamous past and learn why Pendleton was known as the entertainment capital of Eastern Oregon, is going on a Pendleton Underground Tour. The 90-minute tour guides you through a network of rooms and passways in Pendleton’s red-light district.

The most primitive area of the tour is the Chinese living quarter, jail, and opium den. Here you can understand how Chinese immigrants played a giant role in building Eastern Oregon and were one of the main pillars in building the West.

In addition to the underground rooms, you’ll visit one of Pendleton’s 18 bordellos; the famous “Cozy Rooms“. Here the story of Stella Darby and her working girls is told. Make sure to listen carefully to the true tales of brothels, bootlegging, and gambling.

The tours are run by Pendleton Underground Tours, a local non-profit established in 1989 and led by knowledgeable historians (featured on tv, and radio shows worldwide).

Tickets: $20 per person / $15 for visitors age 6-12

#6 Taste local spirits

Pendleton Whisky celebrates the spirit of the American cowboy & cowgirl, well-known beyond the state and country. Fun fact, Pendleton Whisky is a brand of blended Canadian whisky, distilled in Canada, imported and bottled by Hood River Distillers in Hood River, Oregon – not in Pendleton.

However, Pendleton is a great spot to taste local spirits. And a great place to do so is Oregon Grain Growers Distillery. More details are below in the „Where to eat in Pendleton“ section.

#7 Explore Pendleton’s surroundings

For its size (17,000 residents), Pendleton has lots to offer. But outside the town of Pendleton, more activities are waiting. Activities nearby include:

• Whisky and Rocks Farm Loop taste wine, food, cider, cheese, beer, berries, whisky & more
• Wildhorse Resort & Casino – Las Vegas-style casino
• Tamástslikt Cultural Institute: museum and cultural center of Cayuse, Umatilla, and Walla Walla Tribes

#8 Plan your trip to Pendleton around an event

Traveling to Pendleton during one of their major events in summer definitely makes you experience the town through different eyes. Just be aware and don’t expect many shops and local makers to be open the day after a major event. In Pendleton, they know how to party, but also appreciate a day to rest. 🙂 For me as a German, I like that. Events in Pendleton, Oregon:

Pendleton Whisky Music Festival, July

The Pendleton Whisky Music Fest means one big day filled with whiskey, wine, beer, food trucks, camping, country, and some good old rock‘n’roll. Located at the Pendleton Round-Up grounds, this festival attracts music fans from across the state and beyond.

Known as one of the biggest music festivals in Oregon, it features some of the hottest artists in the music industry. For the 7th annual Pendleton Whisky Music Fest on July 15, 2023, Kane Brown, Flo Rida, Niko Moon, Dylan Schneider, and Maddie and Tae made the crowds dance and sing along.

The Pendleton Whisky Fest offers a free shuttle service taking music goers to and from the Stadium, making it super convenient to travel from town to the festival and back.

Pendleton Round-Up, September

Pendleton is home to the largest, most-respected rodeos in the nation for over a century. For over 100 years the continuing Native American participation, strong volunteer corps, and community support have made this one of the largest and most beloved rodeos on the continent.

The first Pendleton Round-Up was held on September 29, 1910. Today it is a multi-day-long celebration of Western heritage. The rodeo gets kicked off with a dress-up parade and ends with the crowning rodeo champions. In between it’s filled with concerts, a night pageant, and more, thrilling tens of thousands of cowboys and cowgirls (and those who want to be) every year.

Pendelton Round-Up 2023: September 13 -16

Can’t make it to the Round-Up? Visit the Happy Canyon Hall of Fame, a museum devoted to rodeo and its legacy.

For more events check out Travel Pendleton’s website

Where to eat in Pendleton, Oregon?

Hamley Café

Hamley Café is the spot to sit back and relax while sipping on your morning coffee. You can choose between pastries, scrambles, sandwiches, or classic biscuits and Hamley sausage gravy. You can sit outside or in the second-story loft, full of comfy couches for a private quiet space. 

Part of Hamley’s & Co is Hamley Steakhouse & Saloon, known for Ranch Cookin’, prime grade steak & impressive Old West ambiance.

Rainbow Café

Established in 1883, Rainbow Café and Bar is Oregon’s oldest tavern. Located right on Main Street this classic breakfast joint offers 3-egg omelets and sweet items hot off the griddle.

Imagine a typical American diner filled with comfy booths with a collection of photos from Pendleton Round-Up winners on the walls. Rainbow Café is known to be where close friends meet for good food and good times. The bar is open until 2 am.

Sisters Café

Nestled in the heart of downtown, Sisters Café has a cozy, welcoming atmosphere. Their diverse menu includes crafting dishes that work for meat lovers and are vegan-friendly. Sisters Café is best known for its sweet and savory crepes, flatbread pizza, and specialty sandwiches.

Great Pacific Wine & Coffee Co

Located in the old Masonic Lodge on the corner of Main Street, The Great Pacific took a new approach to its original purpose: Built in 1887, the historical building was a gathering place for town meetings and housed local businesses on the ground floor. In 1980 the lodge became Eastern Oregon’s first wine and espresso bar.

Today, this restaurant makes you feel right at home serving delicious dishes, hosting live music, and pouring some of the finest wine in Pendleton. The Great Pacific is loved for their extensive menu, wine, and beer selection as well as the use of fresh, and locally grown ingredients.

Oregon Grain Growers Brand Distillery

This family-owned and operated establishment prides itself as the first distillery in Pendleton, Oregon, since prohibition. The  Bullington family focuses on gathering locally sourced ingredients to be made into high-quality craft spirits to pay homage to the hard-working growers that make it possible.

Located near downtown, Oregon Grain welcomes visitors to stop by for a distillery tour to see where all the magic happens. At the tasting room, you can savor up to 4 free samples and purchase your very own bottle of locally-made vodka, gin, and whiskey.

Oregon Grain Growers Brand Distillery turned out to be our favorite eatery in Pendleton.

Where to stay? Motolodge Pendleton

Situated along the original Oregon Trail, halfway between Portland and Boise (Idaho), Motolodge Pendleton has 40-rooms, a pool to cool off during hot summer days, and a Pendelton Whisky barrel sauna and whirlpool to warm up during Pendleton’s heavy winters.

The independent boutique hotel is Pendleton’s newest hotel. The Fully renovated 1950s motel offers a modern-day experience with the nostalgia of the good ol’ days. Free parking, free coffee in the lobby, and dog-friendliness make Motolodge a convenient hub to explore the town by foot and a great stop on your Eastern Oregon road trip.

Prizes start at $140/night for a Moto King Room on the weekend (2 nights) in August / $120 in October + taxes + fees.

Roadtrip Eastern Oregon

If you happen to road trip Eastern Oregon and come through Pendleton, make sure to stop and check out the lively town!

Great stops to include in your Eastern Oregon Roadtrip:

Wallowas – one of Oregon’s Seven Wonders, the Wallowa mountains are known as “Little Switzerland”, a popular destination for hiking and backpacking. The town of Joseph is the gateway to Wallowas and 120 mi / 190 km away from Pendleton (2.5 hrs drive)

Hell’s Canyon – If you want to visit America’s deepest river gorge, Hell’s Canyon, you must continue your journey east. Hell’s Canyon and the Snake River mark the border to Idaho. To visit, drive to Oxbow (160 mi / 260 km and 3h from Pendleton) and continue your drive on Idaho’s side of the Snake River to Hell’s Canyon Dam.

Painted Hills – another of Oregon’s Seven Wonders is located within the John Day Fossil Beds National Monument, 170 mi / 275 km southwest of Pendleton (3.5 hr drive).

The Walla Walla community, one of the finest wine regions in the nation is only 40 mi / 65 km away (50 min. drive), located in Washington State.

More Oregon towns to explore

• Seaside – Weekend Guide to explore Portland’s closest coast town
• Bend – Gateway to the great outdoors of Oregon

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QUESTIONS & COMMENTS?

Have you ever been to Oregon and explored towns like Pendleton? Do you like the article, and have suggestions, feedback, or recommendations? Leave me a comment and please feel free to share this article with your friends!

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