West Coast Road Trip From San Francisco to Portland

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  • San Francisco
  • Redwood Forest
  • Oregon
  • Portland
  • Roadside assistance with Jerry
There’s no shortage of things to do on a road trip from San Francisco to Portland —luxuriate in the historic Golden Gate Park before enjoying the city’s musical and literary spots; then head north through Redwood country and Oregon’s lush interior on the way to hip, oddball-friendly Portland.
Whether you’re dead set on finding San Francisco’s best loaf of sourdough bread, or ready to hit the road in search of Portland’s finest coffee and donut combination, you’ll want to make sure you’re protected with car insurance before you head out.
By using Jerry, you can score a great car insurance policy at an affordable rate. Signup takes just 45 seconds, and then Jerry will fill your screen with up to 50 quotes from the country’s top insurance providers. All you have to do is pick your policy, and then this AI-powered car insurance broker and comparison shopping app does the rest.
Keep reading for the best road trip from San Francisco California to Portland, Oregon.
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Start—San Francisco

Start your journey in San Francisco, California’s vibrant darling. Try to spend more than one night and don’t miss checking out Golden Gate Park, San Fran’s unparalleled musical and literary scene, and eating options.

What you should do

Explore Golden Gate Park: Stretching from Haight Ashbury west to Ocean Beach (and the Pacific Ocean) is Golden Gate Park, San Francisco’s answer to New York’s Central Park. Golden Gate more than holds its own as the west coast’s premier urban park, featuring gardens, museums, hiking trails, and more amongst its 1000 acres.
While you’re there, check out the Japanese Tea Garden. This gorgeous, peaceful spot pays homage to Japanese horticulture, design, and food. Wander through bonsai trees and cherry blossoms, over and across charming bridges overlooking koi ponds, and indulge in a green tea and fortune cookie at the garden’s tea house. The Tea Garden dates back to 1894.
Near the Tea Garden, you’ll find the deYoung, one of the city’s oldest museums. It offers a vast, global art collection dating back to the 17th century. Make your way to the top of the museum tower (which is free of charge) for panoramic views of the park and San Francisco.
Browse at Amoeba Music: Records, CDs, and cassettes (not to mention 45s) may be the products of yesteryear, but Amoeba Music is a San Francisco music establishment doing its best to keep tactile musical products in vogue.
Just east of the park, Amoeba is a garden of musical delight, featuring all the records, compact discs, posters, books, and merch any music fan could ask for—indie, contemporary, vintage, whatever—it’s all here.
Amoeba may be one of the last of a truly dying breed—a giant, multi-floor record store that features in-store shows and a truly kaleidoscopic musical selection. If you love music, treat yourself to a visit. There’s an Amoeba in Berkeley, too.
Find your new favorite book at City Lights Booksellers & Publishers: A legendary North Beach locale, City Lights Booksellers & Publishers opened in 1953 and is best known for publishing Allen Ginsberg’s poem “Howl,” cementing its place in Beatnik legend.
Meander through City Lights’ three stories and find all the poetry, fiction, and non-fiction your page-turning heart desires. Once you’ve made your selection (or…selections), grab a coffee at one of the many neighborhood cafes.
Blue waves crash on a beach with the Golden Gate Bridge in the background.
San Francisco, California
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Leg 1—California’s Redwood Forest

Drive 4 hours towards Mendocino and into Ferndale, along CA-1 to US101-N
Before laying eyes on California’s majestic Redwood Forest, head up the coast towards the artsy town of Mendocino. From Mendocino, head northeast on the 101 towards Humboldt State Redwoods Park, where you’ll soon find yourself amidst the towering Redwood trees guarding this foggy stretch of Northern California coastline.

What you should do

Marvel at the Avenue of Giants: Hop onto The Avenue of the Giants (State Route 254) to drive through the park and experience these monster trees from the car. There are eight stopping points along the way to get out and marvel at these enormous specimens. You’ll feel truly tiny amongst them.
Sleep at the Shaw House Inn: After realizing amidst the Redwoods that we’re all mere travelers on this Earth (as opposed to those giant trees, which aren’t going anywhere), rest your contemplative head in the charming town of **Ferndale, specifically at the Shaw House Inn.
This quaint, cozy, Victorian bed and breakfast is tucked away in a gorgeous private garden an acre in size. The Shaw House was actually the first home built in town and features eight sumptuous guestrooms. As an added bonus, the Inn is pet-friendly, so Fido and Felix can come along.
A stretch of road trails through the Redwood Forest with trees standing overhead.
California’s Redwood Forest

Leg 2—Cross into Oregon

Head to Gold Hill, OR, 4 hours driving time along US 101-N and US 199-N
After a night in Ferndale, head north along US101 and then tack right onto US199-N, crossing into Oregon’s green underbelly and heading towards The Oregon Vortex and some wonderful weirdness. After that, you’ll head north again and spend the night in Eugene, a hip university town.

What you should do

Explore the Oregon Vortex and the House of Mystery: Some people think San Francisco is weird—well, once you enter The Oregon Vortex and House of Mystery, your ideas about gravity and perspective will be forever altered, and “weird” will have new meaning.
A roadside attraction in Gold Hill, The Vortex has been warping peoples’ minds since 1930. At the heart of all the weirdness is, as the proprietors tell it, the vortex, or a “spherical field of force” similar to a whirlpool, situated half above ground, and half below.
The results are positively mind-bending—within the area, no one stands upright, as if your body is being pulled north by a magnetic force. People appear to change shape—appearing taller as they move away from you, yet shorter when they approach. Crazy? Perhaps…
Stay in Eugene: After you’ve been thoroughly, joyously spooked, find your bearings, head to Eugene, and stroll through 5th Street Public Market, home to shops, restaurants, events, and live music nearly every night of the week.
Then, before hitting the sack at The Gordon, an artsy new hotel located smack dab in the Market, check out the hotel’s collection of more than 160 pieces of art by more than 80 artists. You can even create your own art in The Gordon’s Art Lobby, which the hotel keeps stocked with paints and pencils for guests’ use.
A road leads into a foggy forest and a "Welcome to Oregon" sign stands to the right of it.
Oregon

Arrive in—Portland

Head north on I-5 from Eugene to Portland for 1 hour and 40 minutes
After a night in Eugene, you’ll roll into Portland, known as one of the most creative-forward cities in the U.S. What to do? Where to start? We’ll tell you.

What you should do

Tour the USS Blueback: If you’re surprised that a decommissioned U.S. submarine sits half-submerged in the Willamette River about a mile from downtown, you’re right to be. Now, some people think only the Canadian Navy had diesel-electric submarines in its fleet, but you’d be wrong!
The USS Blueback, which calls the Willamette home, was the U.S. Navy’s last diesel-electric sub and was taken out of service in 1990 after more than 30 years of active duty.
It’s now an interactive exhibit as part of the Oregon Museum of Science and Industry. Tours are available and visitors can scoot through the sub’s narrow hallways, check out its tight quarters, squawk mayday calls from the radio room (ok, not really), and look through the periscope.
We knew you’d ask, so we’ll just tell you—the torpedoes were removed long ago. Sorry.
Watch a roller derby match: After spending time in a buttoned-down submarine, head over to The Hangar at Oaks Amusement Park to catch a Roller City Rollers roller derby match, and get ready for a rowdy, rambunctious, and raucous good time.
Big hits, lots of music, and a frenzied atmosphere make this a true Portland attraction. Once the match is over, head down onto the floor to high-five the rollers for a match well played.
Satiate your sweet tooth at Voodoo Doughnut and Wedding Chapel: Since this is a road trip (by that we mean vacation), you’re allowed to have a diet of strictly sugar, which makes visiting Portland’s zany Voodoo Doughnut and Wedding Chapel a must.
Take your pick from a smorgasbord of deliciously sweet delights, among them—Cap’n Crunch, Hi-Tea, Butterfingering, School Daze PB&J.
And, yes—you can get married here. The Wedding Chapel offers several legally-backed wedding packages, as well as commitment ceremony plans. Not surprisingly, the packages include refreshments. Guess what those are?
Stay at The Sentinel: After gorging yourself on Portland’s sweet offerings, you’re gonna need to sleep all that sucrose off, so might as well do it in style—stay at The Sentinel, a brilliant marriage of old-world ornateness and modern luxury.
The Sentinel consists of two older structures—a former Elks Lodge, and the remnants of The Seward, a boutique hotel that dates back to the early 20th century. Inside the 100-room hotel, you’ll find a cocktail bar—Jackknife—with a stained glass ceiling, as well as the Domaine Serene Wine Lounge, featuring wines from nearby Willamette Valley wineries.
If you need some coffee after a day and night of sugar and booze (let’s stay responsible, folks) The Sentinel is just a few blocks away from Portland coffee icons Coava and Stumptown.
A landscape shot of Oregon taken at sunset.
Portland, Oregon
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Roadside assistance with Jerry

If you’re heading on a road trip from San Francisco into the Pacific Northwest, Jerry has your back with its new emergency roadside assistance program.
If your car breaks down on the road, you’ll never be in the lurch. Towing, tire fixes, winching, Uber credits, and more will be at your service in case your trip careens off course.
And what better to pair with roadside assistance than car insurance? You need to protect yourself and your vehicle, and Jerry can help you do just that. Powered by AI, Jerry can help you score the best insurance policy at an affordable price.
Sign-up takes 45 seconds (roughly the time it takes to inhale a box of Voodoo Doughnuts), and then Jerry generates up to 50 quotes from top insurers for you to pick from. Jerry will sign you up for your new policy and cancel your old one. What should you do? Sit back and enjoy those doughnuts.
“Couldn’t be easier. These guys are pretty awesome. I hate searching for car insurance because it’s time-consuming looking for the cheapest one. Jerrydid all of that for me in a few minutes!”—Connor B.
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