Oregon was once home to the “Frontier” and small towns that today we’d call the “Wild West,” but few places remain where you’ll find that Western spirit quite like Eastern Oregon. Just a few hours east of the Portland metropolitan area you’ll find that the West is still alive and kicking its cowboy boots in Pendleton, Baker City, and La Grande.

Pendleton and many other eastern cities have earned a popular reputation for their rich cultural heritage stemming from a history as booming frontier towns located along the Oregon Trail, and also as areas that have long been historical and cultural centers for Native American tribes. This summer, explore Eastern Oregon and get a taste of that Wild West flavor on a road trip that takes you not just a few hundred miles to the east, but a couple of hundred years into the past as well.

The Route: Pendleton, La Grande, Baker City

The Drive: As you follow Interstate 84 East, you’ll enjoy the stunning beauty of the Northwest’s pride and joy, the Columbia River Gorge. Before arriving in Pendleton (3.5 hours from Portland) you’ll see the landscape begin to morph into the wild terrain of Eastern Oregon where desert, rushing rivers, and rolling hills intertwine. From Pendleton to La Grande (1 hour), enjoy the interchanging landscapes of lush green spaces and rugged mountains as you follow along the Old Oregon Trail Highway section of I-84. The La Grande to Baker City route (45 minutes) opens up to views of high desert and green hills, or you can opt to take the much longer but dramatically beautiful Hells Canyon Scenic Byway around the Wallowa Mountains on your journey to Baker City. Head quickly back to the metro area by retracing your route about 5 hours to return to Portland, or extend your route by heading further eastward or looping through some of Central Oregon’s beautiful regions before returning up I-5.

Pendleton:

The 16,000 citizens of Pendleton live up to the town motto “The Real West,” every day of the year in their western-themed shops, historic “old town,” and at the many events and festivals honoring the Wild West. Throughout town you’ll find shops where you can purchase a pair of boots, a hand-crafted leather belt, wallet, or even a saddle, or just browse the eclectic variety of Western duds. When you arrive in Pendleton, visit the Chamber of Commerce to pick up the Real West Charm Trail map to enjoy a self-guided tour of the city’s museums, stores, restaurants, and historic landmarks or blaze your own trail to a few of these favorite Pendleton destinations:

• Farmer’s Market: From May to October, every Friday on Main Street, this popular market features a selection of farm fresh produce, handmade crafts, food vendors, and live music.
• Pendleton Woolen Mills: Tour this factory and museum to learn about the history of the company and the famous Pendleton wool blankets known for their beautiful geometric designs.
• Umatilla County Historical Society Museum: This informative museum showcases historic photographs, artifacts from the sheep industry and wool mills, local Native American artifacts, and a railroad telegraph system and train buffs will love the location in an old train depot built in 1909.
• Wildhorse Resort & Casino: Test your luck at the tables of this casino or visit their Tamástslikt Cultural Institute museum to learn about the Cayuse, Umatilla and Walla Walla tribes.

Must-Sees:

Pendleton Underground Tours:
Tour what was once the red light district of Pendleton through properties now recognized as National Historic Places. During the tour you’ll view the original sidewalks and basalt-rock tunnels of the city which date to before the 1890s, walk through tunnels that were built by Chinese workers from 1870 to 1930, and see sites that include ice plants, butcher shops, Chinese laundries, illegal saloons, bordellos, and opium dens. Up above ground, you can tour the “Cozy Room” to view Miss Stella’s bordello and boarding house. Once a year the tour hosts the special “Come to Life” event during which re-enactors play the parts of historical characters for an exciting and riotous two-hour tour.

Pendleton Round-Up:
Oregon’s most famous rodeo, also recognized as one of America’s greatest, dates all the way back to 1910. The Round-Up takes place during the second full week of September and features a cowboy breakfast, a parade, a country music concert, dances, art shows, and a pageant each night which celebrates Pendleton’s pioneer and Native American heritage. The Round-Up is so popular that the population jumps from 16,000 to about 45,000 during the four day event. Also at the time of the rodeo, visitors and locals gather to view the Professional Bull Riders Classic and the Happy Canyon Pageant, a powwow put on by the Confederated Tribes of the Umatilla Reservation.

La Grande

This Eastern Oregon town, just a hair smaller than Pendleton, shares the same Western heritage, but is also one of Oregon’s hot spots for outdoor recreation. La Grande is located near the Wallowa-Whitman National Forest where you’ll find more than 1,700 miles of trails for hiking and mountain biking, as well as lakes and campgrounds for every type of traveler.

In La Grande most visitors enjoy touring the downtown area to see turn-of-the-century architecture and to visit the historic commercial district, a National Historic Place.

Baker City

The small town of Baker City, less than an hour from La Grande, is a tourist favorite for its charming historic center and its many annual festivals, the most well-known of which, the Miners’ Jubilee, celebrating the town’s mining history, takes place each July. On a visit to Baker City you’ll enjoy touring the 130 properties that make up the Baker Historic District, but if you only have time to see the top attractions here are a few Baker City must-sees:

• The Geiser Grand Hotel: This National Historic Landmark hotel dates to 1889 and has received national recognition for its service and well-preserved architecture. Ghost hunters and thrill seekers might also enjoy touring the hotel because it is rumored to be haunted.
• Baker City Tower: This historic art deco building isn’t much of a sky-scraper at only 9 stories tall, but it is still the tallest building in Oregon east of the Cascade Range.
• National Historic Oregon Trail Interpretive Center: Just 5 miles east of town you’ll find the region’s most visited attraction, a living history museum with demonstrations, interpretive programs, exhibits, multi-media presentations and special events throughout the year. Check the center’s event calendar before you head out for special events including Dutch Oven Cooking Workshops, Meet the Pioneers’ Day on Memorial Day featuring re-enactors demonstrating pioneer crafts and performances of historical events, and the Labor Day Wagon Encampment during which historic re-enactors present an Oregon Trail pioneer wagon camp, the center’s most popular event.

Extend your road-trip

If you have an extra day or two to spare, you won’t regret taking the Hells Canyon All-American Road past the Imnaha River and the Wallowa-Whitman National Forest along the Snake River through Hells Canyon, a gorge that, at 7,900 feet, is deeper than the Grand Canyon.

The scenic byway loops around the Wallowa Mountains beginning in La Grande and ending in Baker City. Along the scenic byway you will pass a series of small towns that have earned big reputations for their frontier histories and lively recreation scenes.

Make sure to stop at the Hells Canyon Overlook, between Joseph and Oxbow, for spectacular views. For an extra thrill, stop in Hells Canyon for a Jet Boat Tour. If you time your journey just right, you might be in the 1,000-resident town of Joseph, along the scenic byway, for the Chief Joseph Days Rodeo in July or the Bronze, Blues, and Brews biker-friendly music and beer festival in August, two of Eastern Oregon’s most-visited summer festivals.