When you prepare for a grand road trip, a few questions might run through your head: Is the driving playlist up to date? When was the car’s last oil change? Are there enough snacks?
But for BIPOC travelers (Black, Indigenous, people of color), there’s another question that might arise: Will I travel through a city that might target me based on the color of my skin? I am an avid road tripper, but after a cross-country experience where I was followed for miles until I had to wait inside a Walmart for them to leave, it is something that I think about every time I prepare for a long drive.
Travel for people of color is dangerous. Even after the abolishment of slavery, violent racial injustice against BIPOC persisted in America through the introduction of Jim Crow laws, Indigenous removal acts, internment camps, Asian exclusion acts and other discriminatory measures. Travel during segregation and beyond has been dangerous because white supremacy is technically upheld by the law.
“The Negro Motorist Green Book,” written by Hugo Victor Green in 1936, was a travel guide written specifically to help Black people navigate to attractions in the U.S. and Canada that were deemed safe during segregation. It helped travelers avoid dangerous “sundown” towns that were notorious for harassing and attacking people of color who came through.
Even Oregon, coined one of the most progressive states, upheld such racist ideals, with laws that prohibited Black people from living or even entering the state. As recently as 2002, the Oregon Constitution stated that “no free Negro, or mulatto … shall come, reside, or be within this State, or hold any real estate.” Oregon’s current population is about 2% Black, mostly concentrated in Portland. So skepticism from Black road-trippers through Oregon is valid.
However, as a Black woman living and working in Oregon, I have found incredible road-trip gems throughout the state that are comfortable and welcoming to BIPOC travelers. See my road-trip tips for Black travelers, including basic safety measures like avoiding empty gas stations and driving late at night, research the area, and carry a physical map or itinerary of where you’re going. And another big tip: support BIPOC businesses whenever you go.
I have been traveling across Oregon for over a decade now, and with each new road trip and weekend getaway, I’ve learned something new about the state’s history, culture and landscape. Follow these multi-day road-trip itineraries for some of the best experiences Oregon has to offer, and see what Black-owned businesses you can support along the way, including those suggested here.
Starting your drive from Portland, head toward the Coast to stop in Astoria. Movie lovers will enjoy seeing sites from the classic films shot here, like “The Goonies,” “Free Willy” and “The Ring Two.” Grab a sweet snack from The Naked Lemon bakery before you head out.
Driving south on Highway 101, you’ll pass markers and statues of Lewis and Clark, as they ended their expedition at the Oregon Coast. Oregon filmmaker Ron Craig produced the documentary “Searching for York,” which shows the journey of the only enslaved man on the expedition, York, and is a must-watch before cruising down the Coast.
I recommend stretching your legs in the town of Tillamook, and grabbing lunch to go or to enjoy outside at the Tillamook Creamery. Visitors can take a self-guided tour through the factory to learn the behind-the-scenes of cheesemaking. End your day in Yachats and walk along the tide pools until sunset.
Wake up bright and early to continue your drive down to Florence, where you can either check out the Oregon Sea Lion Caves (the largest in the nation!) or hit the sand dunes in an ATV rental. If you would like an extra day on the Coast, keep driving to Brookings to see the dramatic rock arches at Harris Beach State Park and stay overnight. Otherwise, head to Southern Oregon for the next leg of your trip. While I didn’t see many Black residents along the Coast, I also didn’t necessarily feel like I stood out in any way, because the Coast is a busy area with lots of tourists from both out of state and bigger cities in Oregon.
If your road trip is between March and November, there is a good chance it might overlap with an Oregon Shakespeare Festival performance in Ashland, led by artistic director Nataki Garrett. Check out the latest season’s lineup of performances, ranging from classic Shakespeare to modern musicals, comedies, dramas and short films produced by BIPOC artists. (Sidenote: Check out the short film “You Go Girl,” produced by a Southern Oregon-based film crew, which premiered at the prestigious Sundance Film Festival in January 2022.
Then you’ll want to spend a day or two in Oregon’s only national park, Crater Lake. The lake was formed after the eruption of the ancient volcano Mt. Mazama, sacred to the indigenous Makalak people of the area. Visitors can hike around the country’s deepest lake, including trails that are fully wheelchair accessible.
I was the most nervous about traveling through Southern Oregon, but Ashland was very welcoming and friendly, and I didn’t get ignored by business owners or waiters like I had in other rural areas. The National Park Service always does a fantastic job of ensuring a safe and comfortable environment for all of its visitors, and Crater Lake upheld that standard.
If you have time, make the trip out to Central Oregon. Stay at the LOGE Hotel in Bend, which gives back to a variety of local community groups that foster responsible access to the outdoors and stewardship of the environment. One of the partner programs is the Central Oregon Trail Alliance, a volunteer nonprofit that builds and maintains trails throughout the region for use by all.
From Bend you can explore nearby natural beauties by stand-up paddling on the river or heading out to Smith Rock State Park for a hike or horseback ride (highly recommend Smith Rock Trail Rides; they went above and beyond for customer service). Avoid crowds and parking hassles by heading out early and visiting on weekdays. To accompany you on your adventures, you can pick up a high-tech musical instrument from BIPOC-owned Outdoor Ukulele, specifically designed to be taken out on the trails.
Bend was probably my favorite stop on my Oregon road trips, even though it is almost three hours away from Portland. The population is more diverse than I had expected for Central Oregon. And the vibe of the town itself is energetic, lively and down to earth. On top of that, the surrounding areas are absolutely stunning to drive through, with vistas of the Three Sisters mountains and other Cascade mountain peaks. Even if you don’t consider yourself an outdoorsy person, everyone is enthusiastic about encouraging you to try new activities.
Looking for an easy trip from Portland? There’s so much to see and do in the verdant Willamette Valley, between the world-class wineries and farm-fresh food to healing hot springs, waterfall trails for hiking, quiet small towns for a slower pace, and vibrant array of arts and cultural attractions like Woodburn’s “Little Mexico” and historic covered bridges. Make the lovely drive south to Eugene to explore the easygoing vibe, and grab a bite at the family-owned Caribbean food truck Irie Jamaican Kitchen. Heading back north, know that at the Oregon State Capitol building in Salem, the Oregon Black Pioneers group leads events and exhibitions focused on Black history and heritage in the state. For vino enthusiasts, book a wine tour with Dirty Radish to get a more intimate encounter with the various winemakers, butchers, chefs, cheesemakers and artisans in the Willamette Valley.
If you have any extra time before leaving Oregon, hang out in Portland. Grab a morning coffee at Deadstock Coffee downtown or Elevated Coffee in the Alberta District, one of Portland’s historically Black neighborhoods. As a foodie city, Portland has a plethora of restaurants, including West African cuisine at Akadi, barbecue at Southern Kitchen, and soul-food carts like Trap Kitchen and Right Bayou Cajun.
Portland as a whole is a pleasant city, with ample trees and cute boutiques, but when I first came to Portland, the stark absence of diversity was jarring. Often I am one of the only Black people in a restaurant, or having a picnic on the waterfront, or even in a classroom or work group. But despite the state’s history of discrimination and disruption of Black neighborhoods, there is a strong Black community in Portland. Groups like the Urban League of Portland — the city’s oldest civil rights organization — are committed to empowering Portland’s African American community and others when it comes to daily life or traveling through town.
“There will be a day sometime in the near future when this guide will not have to be published. That is when we as a race will have equal opportunities and privileges in the United States.”
— Victor Hugo Green, “The Negro Motorist Green Book”