Three Days in Pendleton




Despite its stature as one of Eastern Oregon’s largest cities, weighing in at 17,000 people, Pendleton holds onto its small-town charm and has no shortage of personality. Fueled by wide open spaces, majestic mountain ranges, and the spirit of the wild west, the town provides instant gratification for those looking to escape the metropolitan bustle for a good old-fashioned time. Built on the hard work of Oregon Trail pioneers, rodeo riders, proprietors, and a lot of grit, there’s a vibe you can’t quite put your finger on. And the best way to understand it is to head out to Pendleton and experience it for yourself. To get you started, we’ve put together an easy three-day itinerary where you’ll find your fill of where to stay, what to eat and drink, and plenty of good times.


Located just off Interstate 84, traveling to Pendleton by car couldn’t be easier. A straight shot at just over three hours from Portland to the west, and just under three and a half hours from Boise to the east, it’s an easy destination for your next adventure.


For those who prefer flying, the Pendleton Airport offers three daily round-trip flights from Portland, which makes it easy to turn that work trip into a weekend getaway, or a hassle-free, car-free escape.

Boutique Air


If nostalgic urban vibes and Instagram-worthy shots are your scene, look no further than Pendleton’s newest motel, MotoLodge, whose American heritage-inspired decor, seasonal outdoor heated pool, and 6-person Pendleton Whisky™ Barrel Sauna celebrate the open road and the wild west. Or book a stay at the Pendleton House Historic Inn and bask in European elegance and refinement, magnificent views from the front porch, and gourmet breakfast. Opt for a family-friendly stay with a full breakfast and indoor pool for the kids at Oxford Suites or Hampton Inn, both just minutes from downtown. And if you’re looking for a truly unique experience, stay in Pendleton’s very own bordello, The Working Girls Hotel. This early 1800s boarding house will truly knock your socks off.


The name Pendleton is a brand in and of itself. From woolen mills to rodeos to whisky, these products pay homage to the authenticity, passion, and superior craftsmanship of the town’s residents. Spend the day exploring the history and products that put Pendleton on the map

Early Bird

Start the day with breakfast at Pendleton’s famed Rainbow Cafe. Oregon’s oldest tavern, the Rainbow Cafe, has been in operation since 1883, is a hands-down local favorite, and is as colorful as its name implies. 

Let’s Get Western!

Start at the Pendleton Woolen Mill Store to see where it all began. Here, you can watch their jacquard wool blankets being woven in the original mill, then shop for the perfect blanket, apparel, or other gifts to take home. For the full experience, sign up for a free tour, but be sure to stop in midweek, as tours are not offered on the weekends. Next, it’s off to the world-famous Pendleton Round-Up. If you can’t make the rodeo in mid-September, then catch the next best thing at the Pendleton Round-Up Hall of Fame Museum. Here you’ll learn about the Round-Up’s inductees and the history of the rodeo. Continue the edu-cation at the Heritage Station Museum, a converted 1909 train depot in downtown Pendleton that hosts exhibits about Pendleton and Umatilla County’s rich history. Last, end your afternoon with some levity at the Pendleton Underground Tours, “a place where culture is kept, history is told, and legends live on.” Here, guides dress in period clothing and offer up drinks named after the working girls and old proprietors that once resided upstairs. You’ll tour Pendleton’s unique subterranean tunnel system, passing through the Shamrock Card Room, Hop Sing’s (Chinese Laundry), the Empire Ice Cream Parlor, the Empire Meat Market, and beyond. Those over the age of 21 can book a 5 p.m. tour, which includes a drink and other tasters along the way. Continue the immersive Pendleton experience with a Pendleton Whisky™ in the Shamrock Bar every first Saturday of the month after the tour.

Dine and Drink

Now that you have a solid foundation on all things Pendleton, it is time to wine and dine in true cowboy style with a Barrel-cut filet, topped with bacon and finished with a Pendleton Whiskey demi-glace reduction at Virgil’s at Cimmiyotti’s, a historical landmark in downtown. This restaurant has seen its fair share of history but has remained an iconic Pendleton dining experience since 1959. Finish the evening with a nightcap at The Packard Tavern or live music at Hamley Saloon.


Stroll the streets lined with merchants, makers, and restaurants, and you’ll quickly discover what makes Pendleton special: its people. Fittingly, day two of your Pendleton adventure is all about the local culture. 

Before heading out on the Charm Trail, be sure to load up on some Pendleton Bucks at the Visitor Center. Available in any denomination and valid at almost 40 participating businesses, including some of Pendleton’s many entrepreneurs, makers, and proprietors, Pendleton Bucks work just like a gift card and allow cardholders to support local businesses while receiving specials and discounts in the process. 

Armed with your Charm Trail bracelet and Pendleton Bucks from the Visitor Center, you’re ready to hit the trail. While exploring the businesses on the Charm Trail, take the time to discover the incredible makers who call Pendleton home. Highly skilled as both makers and merchants, you’ll learn about and experience the dedication and heart that goes into their craft. At Alexander’s Artisan Chocolates, chat with French-trained Master Chocolatier Alexander about his chocolate bean-to-bar process. Then, step over to the wine bar and learn how to pair wine with chocolate from Sommelier Steve. A few blocks down the road Staplemans Custom Boot Shop is home to four artisan boot makers who create, customize, and repair leather boots and shoes on-site. See the entire process unfold while you shop the custom footwear.


When you’ve worked up an appetite (and a thirst), stop into Pendleton’s first craft brewery, The Prodigal Son. The brewery pours a lineup of appropriately named Pendleton ales and a full pub-style menu that will satisfy and quench your palate.


Next, it’s over to New York Clothier, a true American haberdashery, where you’ll try on handcrafted clothing designed with American aesthetics. You’ll find vintage-inspired bow ties, custom hand-tailored shirts, and curated lifestyle goods. If you’re lucky, you’ll meet the owners, Kevin and Kay, and learn what drew them to the area from New York to set up shop and make Pendleton home.


Cross the street to LL Bevington to meet maker/owner Linda Bevington. She works as she operates her storefront, creating custom purses and leather goods to accessorize your style and decorate your home.


Once you’ve got your steps in and loaded your trunk with local goods, head to Oregon Grain Growers Brand Distillery. This family-owned and operated establishment is the first post-Prohibition distillery in Pendleton. Focused on locally sourced ingredients and the highest-quality vodka, whisky, rum, and gin, their spirits pay homage to the hard-working growers that make the products possible. Enjoy a pizza in the eatery and taste their many handcrafted spirits.


After a full day of exploring Pendleton’s makers, artisans, and other local stops along the Charm Trail, we understand if you’re ready to call it a night. But if you’re looking to close out the day with one more activity, check out the Get Wild 2023! Live music calendar and catch a show before hitting the hay.


Today it’s time to get outside and get to know Pendleton’s abundance of natural spaces. Surrounded by mountain ranges and wilderness areas, the region hosts ample opportunities to enjoy the town’s year-round recreation opportunities.


On day three, recharge your wellness tank with Pendleton’s sweeping scenery. Begin with a light breakfast and a cup of joe at Buckin Bean Coffee. The only roastery in Umatilla County, the coffee beans roasted on-site are best when paired with their housemade pastries, breakfast, and lunch. With coffee in hand, follow the Pendleton Bronze Trail and get warmed up for an active morning. Scan the QR code on the Bronze Trail website and explore the 20 stops along the trail. From there, continue your walk along the Pendleton River Parkway, a non-motorized path that follows the South Bank of the Umatilla River and provides snapshots of the world-famous Round-Up grounds, parks, and downtown. 


Or, immerse in nature at Umatilla National Forest; here, you can hike, bike, trot, and watch wildlife along the trail system of the North Fork Umatilla Wilderness. Be prepared with trail maps, appropriate footwear, and extra water; the trails can be challenging, and as always, please leave the wilderness area in better condition than you found it. The area’s dense natural beauty and shade trees provide a tranquil place to appreciate and connect with nature. After you’ve worked up an appetite, head back into town and refuel with a taste of Pendleton and an all-American lunch at a local favorite for over 40 years, The Saddle Restaurant and Lounge.

Views of the Blues

After lunch, drive through the Southern Blue Mountain Scenic Loop; the 120-mile route will lead you to small Eastern Oregon towns, over Battle Mountain, and through scenic valleys. Named by early settlers for the blue hue of the pine- and fir-lined ridges, the Blue Mountains, or as the locals say, “The Blues,” blanket the land southeast of Pendleton. The range extends east to the Snake River along the Idaho border, and north into Washington. Green lush rolling hills, remnants of pioneer-era homes, crystal clear lakes, and spectacular mountains will accompany you along the loop, and the Blue Mountains’ extraordinary beauty will leave a lasting impression.

Family Fun

If you’re joining us in summer for family fun, beat the heat at the Pendleton Aquatic Center. With three pools with multiple slides, concessions, and family picnic areas with gas grills, this place is FUN and is sure to wear the kiddos out for the last evening in Pendleton.


End your day with dinner on the patio at Joe’s Fiesta Mexican Grill, where Joe himself will most likely greet you. True to the Pendleton way, you’ll find top-notch service, refreshing drinks, incredible Mexican cuisine, and a whole lot of personality at Joe’s. 


Now that we’ve made the planning easy, and fueled your hunger for excitement, book your stay and LET ’ER BUCK IN PENDLETON