6 Road Trips for Following the Footsteps of Oregon Rebels

Visit Oregon’s rebellious roots with an Oregon road trip 

written by Lee Lewis Husk & Kevin Max

Oregon has always been a place for independent thinkers, those who wanted to do things their own way. Most travel is out right now, but a tour of the places Oregon’s rebels made special is an easy hop over the border. 

1) Oswald West, Political rebel

A young, brash Oswald West was elected governor in 1911, hell bent on saving the coastline from development, granting women the right to vote and stamping out booze from “lawless” mining outposts. 

The 38-year-old declared martial law in 1913 and sent National Guard troops to Copperfield near Baker City to prevent saloons from selling alcohol. In 1912, he convinced the Legislature to join seven other Western states and territories in passing some of the country’s earliest voting rights for women.

But his enduring legacy was saving the beaches from development, which had already claimed 23 miles of tideland. In 1913, he proposed that the Legislature declare the wet sand between high and low tides a public highway, border to border, for transportation purposes. Fifty years later, the Legislature etched the early version into permanency by passing the Oregon Beach Bill, ensuring no one can ever post signs that say “Stay Out, Private Property.” 

The best place to appreciate West’s legacy is the state park named for him. Two hours from Portland, south of Cannon Beach, Oswald West State Park features a rainforest ecosystem, miles of sandy beaches, tidal pools and clifftop views of the Pacific Ocean. 

Spend a day at Short Sand Beach or hike through trails of towering Western red cedars, hemlock and Sitka spruce trees.

Timberline Lodge is a gorgeous example of Oregon ingenuity,
at almost 6,000 feet. (Photo Timberline Lodge)

2) Sam Barlow, Pioneer and trailblazer

Arriving in The Dalles in 1845 after traveling 2,000 miles overland from Missouri, Sam Barlow found himself in the second-most difficult position of his life: pay passage to portage his wagons down the Columbia River or remain on the east side of the Cascade Mountains and not reach his destination in the Willamette Valley. Barlow (who was convicted of killing a man in Indiana with an ax but later pardoned by the governor) couldn’t afford river fare, so he posed a radical idea: build a route around Mount Hood. 

Barlow scouted the southern flank of the peak, climbing to 9,000 feet for a view over the forest canopy. Satisfied he could succeed, he and fellow immigrants cut a trail through the thick forest and made their way to Oregon City. Barlow got permission from the provisional legislature to construct a toll road, which quickly became known as the Barlow Road. 

The 80-mile road opened in 1846, becoming the last overland segment of the Oregon Trail, a major gateway for the thousands of settlers to come.

The wagons are long gone, but their ruts remain for hikers and mountain bikers who follow the historic Barlow Road (roughly parallel with U.S. Highway 26 southeast of Government Camp) in dense old-growth forest and steep hillsides. Soak up history, art and architecture at the magnificent Timberline Lodge, a National Historic Landmark at 5,960 feet. End the day savoring some old-style ales at Mt. Hood Brewing Co. in Government Camp. 

3) Peter Britt, Wine pioneer 

Although his name is synonymous with a modern-day music festival, Peter Britt was best known as a nineteenth-century photographer and horticulturist who opened the Northwest’s first winery.

After emigrating from Switzerland, he settled in the gold mining town of Jacksonville. He stubbornly carried 300 pounds of photographic equipment with him over the Oregon Trail. When gold mining didn’t pan out, he turned to photographic portraits but quickly expanded into landscapes, taking the earliest known photograph of Crater Lake. 

An accomplished horticulturist, he planted pear and peach orchards, even cultivating exotic trees like banana, gingko and jasmine. To protect his trees from frost, he was among the first users of smudge pots. 

Britt correctly judged the Rogue Valley’s Mediterranean climate perfect for grape cultivation and started Valley View Winery in 1858. A century ahead of his time, Britt’s early cultivation of grape vines stopped with his death in 1905. It would be post-prohibition winemakers of the 1960s that reestablished the industry in Southern Oregon.

Drive the back road between Grants Pass and Jacksonville (Oregon 238) and step into any number of family-owned wineries along the Applegate Wine Trail. Try the bubbles at John Michael Champagne Cellars or the Spanish tempranillo at Red Lily Vineyards. Enjoy Plaisance Ranch, which produces both wine and organic grass-fed beef, or stop at Schmidt Family Vineyard for estate-grown wine with wood-fire pizzas. Finish up at Britt’s namesake winery, Valley View, and sample the blended Rogue Red. 

4) Ken Kesey, Anti-establishment writer and rebel 

Born in 1935, Ken Kesey came of age between the beat generation of the 1950s and the hippies of the 1960s. The anti-establishment beatnik intellectuals and the free-love, drug-using, antiwar generation fueled Kesey’s legendary career as a novelist and the much-touted (or scorned) Merry Pranksters, known for acid (LSD) tests and mentorship of the Grateful Dead. 

After graduating from the University of Oregon in 1957, he entered a creative writing fellowship at Stanford University and began work on One Flew Over the Cuckoo’s Nest, published in 1962. The book was inspired by his job on the night shift at Menlo Park Veterans’ Hospital, where he supplemented his income by participating in government studies on psychedelic drugs and reputably talking with patients about their lives while high. 

His second novel, Sometimes a Great Notion, about Oregon logging, was published in 1964. Both novels won critical acclaim and were made into movies filmed in Oregon. The books and writings that followed explored themes of personal freedom versus conformity and etched his reputation as one of the Northwest’s most insightful and influential novelists. 

Eugene’s location in the heart of Oregon offers abundant choices for visitors, from sporting events at the University of Oregon and performing arts to farmers markets, vegan cafes, craft beer, wineries and green spaces. Democrats and independent voters outnumber Republicans almost three to one, bolstering its reputation as a liberal enclave.

Soak up history at Luckey’s Club, one of the state’s oldest bars and featuring the Grateful Dead Family Jam every Thursday. Arrive early at the city’s oldest vegetarian and vegan breakfast favorite, Morning Glory Café. Order biscuits smothered in tantric mushroom gravy. 

A bronze-cast chief Joseph in downtown Joseph is a reminder of the legend and the bronze artists in town.

5) Chief Joseph, Fighter, diplomat and negotiator

The peaceful knoll containing the gravesite of Old Chief Joseph (Tuekakas) overlooks the ancestral home of the Nez Perce around Wallowa Lake and the Wallowa Mountains. But the site belies a violent and tragic chapter in Oregon’s history of broken promises, betrayals and war on Native peoples. 

The old chief died in 1871, leaving his son Joseph (Heinmot Tooyalakekt) to navigate turbulent times ahead. In 1877, the conflict escalated between settlers who moved into the area during the 1860s gold rush and the Nez Perce, resulting in deaths on both sides. Forced to flee, Chief Joseph led 600 Nez Perce 1,400 miles toward the Canadian border, but they were eventually caught and exiled to a reservation in Oklahoma.

Over the ensuing years, Joseph earned a reputation as a diplomat and negotiator, pleading his case in the national press and with politicians, including President Rutherford Hayes. In 1885, the government returned some members to the Nez Perce reservation in Idaho but the rest, including Chief Joseph, went to the Colville Reservation in Washington.

Joseph never gave up the fight to return his people to Eastern Oregon. He died in 1904 in Colville, but his spirit permeates the land of his ancestors. 

Joseph, an outpost in remote northeastern Oregon, surprises visitors with its vibrant art scene, dining options and Arrowhead Chocolates—some of the tastiest coffees, teas and chocolates found anywhere.

Beyond Joseph is serene Wallowa Lake surrounded by the rugged peaks of the Wallowa Mountains and Eagle Cap Wilderness, often referred to as the Little Switzerland of America. Cycle the open roads or ride the Wallowa Lake Tramway to the top of Mount Howard. Stop in at the Discovery Center for a look at the “wild science of the Wallowa Country.”

6) Black jazz in Portland, The North Williams Avenue soul

The year was 1945 and North Williams Avenue, or “the Black Broadway,” was the heart of the African-American community and a worldly jazz scene. Clubs such as the Savoy, Lil’ Sandy’s and the Frat Hall were a few of the most prominent. Sherman Pickett and Pat Patterson, owners of The Dude Ranch on North Williams Avenue, were known as Pic and Pat and for their ability to bring outsize jazz acts to their little club. So perhaps they took it in stride that they had just booked a jazz ensemble that included Roy Eldridge, Al McKibben and the young Thelonious Monk.

This neighborhood was razed in the ’60s for renewal projects such as Memorial Coliseum. Portland’s jazz scene, and all of those who lived nearby, suffered a cultural loss from which it has never recovered.

Today, the music is alive in venues such as the underground speakeasy Jack London Revue on SW 4th Avenue and at the handsome and historic The Benson on SW Broadway. It may not have the same soul as North Williams, but you can catch world-class talent here on select nights.  




Luckey’s Club (temporarily closed due to COVID-19)

Morning Glory Café 


Inn at the 5th 

The Campbell House Inn 



The Dog Spot

Vali’s Alpine Restaurant


Wallowa Lake Lodge

Eagle Cap Wilderness camping



Jack London Revue

The Benson

Clyde’s Prime Rib


The Benson

Hi-Lo Hotel



The Bistro 

Cannon Beach Hardware and Public House 


Arch Cape Inn and Retreat 

Nehalem Bay State Park camping 

Mt. Hood


Mt. Hood Brewing Co. 


Timberline Lodge 

Best Western Mt. Hood Inn 


Wine Country


Mustard Seed Café, Jacksonville

Jacksonville Inn Dinner House 


Wine Country Inn, Jacksonville 

Magnolia Inn, Jacksonville 

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