There’s a place in Eastern Oregon where you can see leather saddles made as they have been for 100 years, where top-40 headliners share the stage with country stars, and where you can retrace the path of the Oregon Trail pioneers that came west along this route more than 175 years ago. That place is Pendleton, where the mix of Old West flavors and new-school artists make it an ideal place to escape for three days. Wagon or not, here’s how to spend three days in Pendleton.
Day 1: Hats, boots and pints
Start at Pendleton’s historic downtown to get a feel for this city along the Umatilla River, which was founded in 1868. Fuel up with breakfast at one of the city’s oldest eateries, the Rainbow Cafe. It’s known for its pressure-cooked fried chicken, but it also gets high praise for its down-home breakfasts.
Take a stroll along the Pendleton River Parkway, an accessible walking trail that winds along the banks of the river. When hunger pangs strike again, try the Hamley Cafe downtown — and remember the name, because after a bite, you’ll want to mosey on over to Hamley & Co., a renowned saddle company next door that’s been in Pendleton since 1905.
From saddles, hats and boots to beer, whiskey and vodka, Pendleton’s craft culture — driven by its pioneering spirit — is one of the most well-regarded in the state. While Oregon’s urban centers have seen the rise of artisan-driven businesses in the past decade, Pendleton’s makers were here long before it was cool — and they’re still around. Stop in at Staplemans Boots & Leather, where creative artisans craft fine cowboy boots. LL Bevington, specializing in handcrafted leather and accessories, is also nearby, as is Montana Peaks Hat Company, a custom hat shop that uses traditional methods. Two blocks away, you’ll find more dapper hats (made with beaver and rabbit fur felt) at the legendary Pendleton Hat Company. And just across the street, you could meet the cowboy artist himself as he handmakes custom saddles and other fine leatherwork items at Rod Retherford Saddlery and Cowboy Art.
Cap off the day with a pint or two and dinner at The Prodigal Son Brewery, a downtown craft brewery that’s been making some of the best beer in Eastern Oregon since 2010.
Day 2: History, whiskey and underground secrets
Start your day with coffee and breakfast at Buckin’ Bean, a locally owned artisan roaster. Learn more about the town’s long history with a quick walk over to the Umatilla County Historical Society’s Heritage Station Museum, then head for a wild ride through 100 years of the famous Pendleton Round-Up through the fascinating displays at the Pendleton Round-Up & Happy Canyon Hall of Fame.
Snap back into modern times with a stop in at Oregon Grain Growers Brand Distillery downtown. This family-owned business is among the new crop of artisans bringing craft food and beverages to Pendleton in a big way. Their specialties include ACME corn whiskey and “Ouragon” vodka, made with Oregon-grown hard red winter wheat — a bit higher in protein and more bitter than the soft white wheat Pendleton is known for.
For a more mysterious adventure, sign up for a 90-minute downtown tour with Pendleton Underground Tours ($15 per person, suitable for kids 6 and up). For more than 30 years, this nonprofit has been offering tours of Pendleton’s former red-light district, including glimpses of old speakeasies, bordellos and a network of underground tunnels used by Chinese laborers more than a century ago.
End with dinner at a downtown Pendleton classic, Virgil’s at Cimmiyotti’s. The restaurant, originally founded in 1959, is known for its steaks as well as its fresh offerings straight from the Pendleton Farmers Market, which is open on Fridays between May and October.
Day 3: Blankets, wagon trains and local beef
Perhaps nothing showcases Pendleton’s original maker mentality more than Pendleton Woolen Mills. The company, originally founded in 1863, still makes its signature wool blankets and fabrics, and offers free weekday tours at its blanket mill, about a mile outside the downtown core.
While you’re here, make sure to dive into the local history of the Oregon Trail, which marked its 175th anniversary in 2018. A landmark on the east end of town notes the 1812 camp of an early exploratory party through Pendleton. It was also the route westbound pioneers took when they came through decades later in the 1840s and beyond before crossing the Umatilla, John Day and Deschutes rivers. Olney Cemetery at the southwest end of town is the final resting place for a few pioneers who perished on the way. For an enlightening experience, spend a few hours at Pendleton’s Tamástslikt Cultural Institute, the only museum located along the Oregon Trail that documents how settlers forever changed the lives of the Native American tribes here.
For gifts to bring home, stop in at Blue Hawk Beads, which showcases incredibly colorful beadwork, and then wind your way back to Hamley Steakhouse, by the same owners of the cafe, to cap off your adventure. The steaks are storied and the setting, complete with an original bank wall is pure Pendleton.
When you go
Pendleton is a prime Eastern Oregon destination anytime of the year. Depending on when you go, a range of annual events spotlighting local art, culture and history can make a visit even more memorable. The most famous is the Pendleton Round-Up in September, a weeklong celebration of the best of the Wild West, including a four-day rodeo. (If you want to attend the Round-Up, make sure to book your lodging months in advance.) Also popular are the Pendleton Whisky Music Fest and Pendleton Bike Week in mid-July, and Oktoberfest Pendleton in mid-October. Or join the Pendleton Round-Up Wagon Train (held each year in late June) and spend six days traveling by horse and wagon on the back roads of the Blue Mountains.
For lodging in Pendleton, options abound, from national hotel brands to more local digs like the Rugged Country Lodge, Pendleton House Historic Inn and the Working Girls Hotel.