Hit the Road in Eastern Oregon

by Allen Cox | Photo © Kongxinzhu / Dreamstime

Besides your clothes, road snacks and water­­—don’t forget car games if you have kids—all you need is five days of free time, a full gas tank and the curiosity to discover what’s around the next bend in the road. Northeastern Oregon’s widely diverse landscape will open up like a picture book about the Old West. You’ll travel on two scenic byways, browse towns that hark back to gold rush days and visit some amazing natural wonders that define Oregon.


As you roll into the historic town of Pendleton—home of the annual Pendleton Round-Up in September—remnants of the early West are everywhere from hitching rings to original buildings in various states of restoration. Pause to feel the vibes of history as you admire what was once and still is an oasis of cowboy culture in Northeast Oregon.

In Pendleton, what doesn’t meet the eye is perhaps the most intriguing: The Pendleton Underground Tour. This guided walk through tunnels below the city’s one-time Chinatown exposes an underbelly where unsavory characters are believed to have gathered to gamble and conduct nefarious business not fit for polite society.

Note about starting your road trip in Pendleton: Avoid Sunday, as many Pendleton attractions, such as the Underground Tour and the Tamástslikt Cultural Institute, are closed that day.

For a meal, stop in at Prodigal Son Brewery, a popular spot for craft beer and delicious pub food. Try the beer sampler for a sip of everything they brew.

Soon after you leave Pendleton on I -84, you’ll come to Wildhorse Resort & Casino, a comfortable spot to relax and bed down for the night. While you’re there, visit the Tamástslikt Cultural Institute to learn about the Cayuse, Umatilla and Walla Walla Tribes’ 10,000 years of history in the region.

La Grande, Elgin, Enterprise & Joseph

This morning takes you on a scenic drive on I-84 across the Blue Mountains. Give in to the temptation to stop at The Oregon Trail Interpretive Park at Blue Mountain Crossing. This historic site is well worth the time for a fresh-air breather among the pine trees and to spot original wheel depressions from intrepid pioneers’ covered wagons.
Continue on to La Grande, home of Eastern Oregon University and gateway to the Hells Canyon Scenic Byway. Here you will exit I-84. This is a good place to stop for refreshments and look around the town. Then follow Highway 82 to Elgin.

Check out the Elgin Opera House, a restored theater built in 1911 as a city hall and performing arts house. Today, it is a working theater with a full season of performances every year. Also in Elgin you can board the Eagle Cap Excursion Train, which makes scheduled runs to Joseph in Wallowa County (reservations recommended). Excursions have different themes, such as railroad history, train robbery and a fall foliage excursion.

The Drive from Elgin to Enterprise and Joseph climbs out of the valley and into the foothills of the Wallowas, one of Oregon’s scenic wonders. If you are not already familiar with the town of Joseph, you are in for a pleasant surprise. A thriving visual arts community has populated Main Street with several first-rate galleries; bronze sculptures adorn every corner, celebrating wildlife and Western themes.

At dinnertime, backtrack a few miles to Enterprise to enjoy a microbrew and a casual meal at Terminal Gravity Brewing. Bed down at 1910 Historic Enterprise House B&B (reservations recommended), an Edwardian mansion that has been lovingly renovated into a spacious inn.

Hells Canyon & Baker City

Rise early, gas up and hit Highway 350 out of Joseph, eventually turning right onto National Forest road 39 and eventually left on Highway 86. (Note: There are no services on the long stretch of NF-39.) This segment of the Hells Canyon Scenic Byway is the Wallowa Mountain Route that traverses deep forest in the Wallowa-Whitman National Forest.

Your destination: Hells Canyon Dam, a 3-hour drive from Joseph. Arrive by 9:30 a.m. to board the thrilling Hells Canyon Adventures jet boat tour on the Snake River. Wear water-resistant clothing (you’ll regret wearing jeans), bring a waterproof camera bag, and be prepared for a ride on one of the wildest and most scenic rivers in America. It’s common to spot bighorn sheep and other wildlife on the shores and canyon walls. If you make reservations for the Kirkwood Adventure, your boat will stop at the remote Kirkwood Living Historical Ranch, where you will be served lunch and have an opportunity to explore the original ranch buildings, most preserved as museums.

After the jetboat tour, complete the drive on the Hells Canyon Scenic Byway by following Highway 86 to Baker City. Stop at the Oregon Trail Interpretive Center to learn about the lives and hardships of pioneers who set out on the famous trail. At the Center, you’ll find exhibits, living history demonstrations, interpretive programs, four-plus miles of interpretive trails and more.

You’ve covered a lot of miles in one day. Nothing will be more inviting than a room at the Geiser Grand Hotel, one of the finest hotels in the Old West. (For more about the Geiser Grand Hotel, see “Restored Historic Hotels” in our Jan/Feb 2015 issue.) Gold was discovered nearby in 1862, and that discovery brought thousands of prospectors to the area. Baker City grew up as a rough and tumble boom town and the Geiser Grand was the stage coach stop and hub of local civilization. Today, you’ll find a working hotel that has been painstakingly restored through careful research and meticulous attention to authentic detail.

Hop a few blocks north up Main Street to sample some award-winning craft brews at Barley Brown’s Beer. Grab a casual bite in their brew pub or opt for a more formal dinner under the stained glass atrium back at the Geiser Grand. As you stroll the town, admire the city’s buildings, many built and gilded with mining fortunes, and many on the National Register of Historic Places. Taking a self-guided walking tour is a fun way to learn about Baker City’s fascinating history; download the walking tour guide at visitbaker.com.

Sumpter, John Day, Painted Hills & Mitchell

Fuel up for the day with a hearty breakfast at Lone Pine Cafe across the street from the Geiser Grand. The cafe is operated by chef transplants from Portland, so allow your palate high expectations and enjoy.

After breakfast, take Highway 7 out of Baker City. You’ve just begun the Journey Through Time Scenic Byway. Your first destination is the town of Sumpter to visit the gold mining dredge that created many a fortune. The old mining operation is well preserved in a state park that interprets the early large-scale process of extracting gold from a river bottom.

After touring Sumpter, continue on Highway 7 and then Highway 26 west to John Day. This historic town is home to one of the most unusual museums in the West and one of the cultural and educational highlights of this scenic byway: the Kam Wah Chung State Heritage Site. Begin your visit at the interpretive center, where you’ll learn about the community of Chinese immigrants who lived in John Day and, in particular, about two men, one a doctor of Chinese medicine and one a businessman who ran their apothecary shop, store and hostel. Park rangers lead tours to the actual home and business of these two men, which has been perfectly preserved as a time capsule with all their possessions intact. This tour is a fascinating and sobering glimpse into a community that, sadly, was often harassed, victimized and treated as second-class citizens.

Next, press on to the John Day Fossil Beds National Monument. You’ll drive through a dramatic landscape of aptly named Picture Gorge to one of the geological wonders of Oregon. Detour onto Highway 19 and visit the Thomas Condon Paleontology Center. Here, you’ll learn about the geology of the Cascade volcanoes, the eruptions that shaped the surrounding landscape and left fossil records of early mammals. You’ll even see a working paleontology lab. If you need to stretch your car legs, hiking trails, from short interpretive trails to longer treks, fan out into the Sheep Rock Unit of the fossil beds.

The next stop on the route (continuing west on Highway 26) is the Painted Hills Unit of the national monument. The Painted Hills are a photographer’s dream. Dramatic and colorful striations decorate the bare hills and canyon faces, and visually shift with time of day and weather. Park the car and take one of the five trails to get a closer view; the ¼-mile Painted Cove Trail has a boardwalk over sections and takes you through an area of brightly colored rocks and hills.

From the Painted Hills, back track on Highway 26 to the small town of Mitchell, where you can spend the night at one of the Painted Hills Vacation Rentals (reservations required), complete houses with kitchens and all housekeeping amenities. Bring groceries (there is a small grocery store in Mitchell) to prepare your own meals or dine at the cafe in town.

On day five, rise at your leisure. Your Eastern Oregon road trip has come to an end. You are approximately 6 to 7 hours from Seattle and about 4 hours from Portland. Head home with your new-found knowledge of the Old West, mental snapshots of contemporary life in rural Northeast Oregon and, above all, indelible memories of landscapes like none other that shape this rugged, unparalleled part of the Northwest.

Plan your Eastern Oregon Road Trip at https://visiteasternoregon.com/