In 2018, the pioneer spirit comes alive in Oregon for the 175th anniversary of the historic Oregon Trail. This famous wagon route, spanning 2,170 miles (3,490 km), was the largest migration in American history. Join us as we rediscover Oregon from the perspective of those brave pioneers — while making your own Oregon Trail story along the way.
Day 1: Snake River to Baker City
The long, twisting Snake River was one of the most difficult passageways of the Oregon Trail, where pioneers risked their lives and possessions to cross the roaring waters. At the south side of the town of Nyssa, an interpretive shelter describes the treacherous Snake River Crossing and the trading post that sold supplies at exorbitant costs.
From Highway 201, signs lead northwest to Keeney Pass, where you can walk along the trail’s original wagon ruts traveled by more than 50,000 pioneers. Continue to the town of Vale, the first stop in Oregon for settlers on the Oregon Trail, and stop at the city park where an interpretive shelter reveals Vale’s history.
Take I-84 to Ontario and, if time allows, visit the Four Rivers Cultural Center, a museum depicting the region’s diverse cultures. Northwest of Ontario at exit 353 is Farewell Bend State Recreation Area and Birch Creek, famous as the point where pioneers left the Snake River after following it for 330 miles; now it’s home to restored covered wagons and Oregon Trail sites. At exit 336, Weatherby Rest Area & Burnt River Canyon features exhibits that describe how the steep ascent was a significant obstacle for the emigrants.
All that adventuring can work up an appetite. Take a late lunch in Baker City, where the historic downtown is perfect for a self-guided culinary walking tour. Located in the historic 1920 natatorium, the Baker Heritage Museum showcases the region’s rich history.
Spend the night at Geiser Grand Hotel, built in the 1880s as a hotel for rich miners, and admire its original furnishings, such as its large stained glass ceiling.
Day 2: Baker City to Pendleton
Pack a wagon and experience stories from the trail at the 500-acre National Historic Oregon Trail Interpretive Center. A 2.5-mile walking trail loops through the area with stops at authentic wagon ruts, remnants of the Flagstaff Gold Mine and a former wagon encampment.
Near North Powder off I-84 at exit 285, discover the history of Madame Dorion where in 1811 she gave birth while traveling with the Wilson-Price Hunt expeditions.
Stop in La Grande for lunch at Side A Brewing, where you can satisfy your appetite for history in a historic firehouse turned brewery.
The steep hillsides of the Blue Mountains can leave you awestruck, but for Oregon Trail emigrants the slopes caused many accidents. See where they camped after the first climb at Hilgard Junction State Park. At exit 248, walk in the footsteps of pioneers at the Oregon Trail Interpretive Park at Blue Mountain Crossing, featuring some of the best-preserved traces of the trail.
For a deep dive into Native American culture, visit the Tamástslikt Cultural Institute in Pendleton, the only museum located along the Oregon Trail that documents how the arrival of settlers forever changed tribal life.
You’ll find rodeo-ready gear at Hamley & Co., famous since 1905 for making the “best saddles a man can ride.” Enjoy dinner at Hamley’s Steakhouse, with a menu boasting everything from old Western comfort food to high-end Northwest cuisine.
Rest your cowboy hat at Red Lion, Oxford Inn & Suites or Hampton Hotel — or if you’re feeling lucky, the Wildhorse Resort & Casino.
Day 3: Pendleton to The Dalles
No visit to Pendleton is complete without a tour of the original Pendleton Woolen Mills, family-owned for 153 years. Walk through the showroom piled high with brightly colored blankets and shirts, and marvel at the wool spinning into fabric on looms.
If you have time to spare, experience the Oregon Trail just like the pioneers did with the Pendleton Round-Up Wagon Train, an offshoot of the Pendleton Round-Up. Every last week of June, a dozen wagons and more than a hundred horses travel from the Blue Mountains to Pendleton, emulating the famous pioneer passage.
Otherwise head to The Dalles to grab lunch at Clock Tower Ales, located in an 1883 courthouse. Next, Fort Dalles and Anderson Homestead offer opportunities to see pioneer artifacts and antique wagons. The former military fort is one of Oregon’s oldest history museums.
Check into Shilo Inn before heading west to Cascade Locks for a dinner cruise aboard the Columbia Gorge Sternwheeler. From the ship deck you can sip a beverage and listen to the captain narrate some of the region’s landmarks and history.
Day 4: Columbia River Gorge and Mt. Hood
After breakfast at the hotel, visit the Columbia Gorge Discovery Center for a specialized program with interpretive staff. Take the Historic Columbia River Highway to Rowena Crest for a nature walk that reveals stunning views of the gorge and famous Rowena Curves.
Next travel to Dufur, a historic town with plenty of charm. Visit the Dufur Historical Society to learn about the town’s first residents, then stop by the historic Balch Hotel for lunch and a history talk. Nearby White River Falls is a worthy detour.
As an alternative to the risky trip down the Columbia River, Barlow Road, a toll road, was built in 1846 as the last overland stretch of the Oregon Trail. Today you can drive U.S. Route 26 from Sandy to Government Camp, which follows a segment of the historic road. Explore sections of the original wagon route at the Barlow Pass Trailhead, as well as the Pioneer Woman’s Grave, discovered by survey crews building the highway in 1924.
Take in the views at the historic Timberline Lodge, a classic mountain hotel built in the 1930s, with carved railings and doors as well as other art from the period. No wagons traveled to this high elevation, but nearby Summit Meadow was a tollgate from 1866 to 1870. Enjoy dinner at one of the lodge’s farm-to-table restaurants.
Spend the night at Timberline Lodge or The Resort at the Mountain in Welches.
Day 5: Mt. Hood to Oregon City
Following breakfast, explore the town of Government Camp, where you might detour to the Mt. Hood Cultural Center & Museum for its extensive collection of historic ski patrol memorabilia. Then it’s just a short drive to Laurel Hill Chute Trail, one of the most difficult grades along the trail. Take one last look at Barlow Road from Jonsrud Viewpoint.
Next drive to Philip Foster Farm in Eagle Creek, the last overnight stop on the Oregon Trail, for a hands-on experience of pioneer history.
The plot thickens in Oregon City, where trail travelers received land assignments. Immerse yourself in stories at the End of the Oregon Trail Interpretive Center, where visitors can don authentic costumes and play pioneer games. Then visit the Museum of the Oregon Territory to see the original land plat of San Francisco, plus views of Willamette Falls.
Finish the day shopping the vintage and resale shops of Main Street Oregon City. Refresh with a themed beer at Oregon City Brewing, where they embrace a modern twist of the Oregon Trail. You earned it.
Modern Pioneers on the Oregon Trail
Looking for more trip inspiration? The following nine bloggers commemorated the Oregon Trail anniversary by visiting the route’s historic locations in Oregon, plus a few contemporary attractions, earning themselves the unofficial title of “modern pioneers.” Follow along their journeys west, from Eastern Oregon, through Mt. Hood & the Columbia River Gorge and ending in the Portland Region. And feel free to copy their itineraries too.
