All Articles How to hit the beach and city in one go in Oregon

How to hit the beach and city in one go in Oregon

Sarah Greaves-Gabbadon on exploring Portland, OR, and the iconic Cannon Beach in one trip.

By Tommie Ethington4 Nov 2022 5 minutes read
View of Portland skyline and Mt. Hood from the Portland Aerial Tram
View of Portland skyline and Mt. Hood from the Portland Aerial Tram
Image: Posnov/Getty Images

In our Where To series, we tag along as eight fascinating travel influencers jaunt from coast to coast in search of the best meals, experiences, and more, all inspired by our Travelers’ Choice Awards. Browse all of the itineraries on our Where To hub.

Sarah Greaves-Gabbadon (@jetsetsarah) calls herself an evangelist for the Caribbean, spreading the word about all that the different tropical islands have to offer. In September, she traveled across the country to the Pacific Northwest to experience a different kind of coastal living.

Day one: Get settled

Rose at the International Rose Test Garden in Portland, Oregon
Lobby at Hotel Grand Stark
Plate of fresh seafood at Jake’s Famous Crawfish
From left to right: International Rose Test Garden in Portland, OR, Lobby at Hotel Grand Stark, Plate of fresh seafood at Jake’s Famous Crawfish
Image: From left to right: Xiao Zhou/Getty Images, Management/Tripadvisor, Management/Tripadvisor

After a day of travel, it’s tempting to check into the Hotel Grand Stark, a Travelers’ Choice Best of the Best winner, and never leave. The spacious rooms boast Bellino linens, and the Nespresso coffee machines, Diptyque bath products, and walk-in rain showers are reason enough to stay put. The contemporary lobby is both a backdrop for abstract sculptures and a work of art itself—think tiled walls, curvaceous furniture, and plenty of Instagrammable vignettes. On the weekends, the attached Bar Chamberlain offers light bites and cocktails with cheeky names like “The Perfect Gentleman” and “Tuition Money.”

When you do venture out, the International Rose Test Garden is the perfect low-key introduction to the City of Roses, and sits just 15 minutes away from the hotel. The Travelers' Choice Award–winning garden is beautiful any time of year with more than 600 different rose varieties, but especially so during peak season: late May through October. Don’t miss the section with blooms named after Shakespearean characters.

For dinner, Jake’s Famous Crawfish nods to the old days of fine dining with wood-paneled walls and stained-glass light fixtures. Seafood options abound, and the fresh fish is where it’s at. Order the Washington steelhead with sautéed Oregon Bay shrimp and basil butter.

Day two: Learn about Portland’s beginnings

Exterior of Pittock Mansion
Fried chicken and roti at Hat Yai
Pittock Mansion (L), Fried chicken and roti at Hat Yai (R)
Image: Teammilitello/Tripadvisor (L), Management/Tripadvisor (R)

Journey across the Willamette River for Cheryl’s on 12th, an airy Travelers' Choice Award–winning café that embodies the city’s diverse dining scene. On the menu, you’ll find tofu rancheros next to a croque-monsieur next to Portuguese fried rice. The latter is a hearty house specialty, perfect for sharing.

From there, make the short drive to Pittock Mansion, the former home of one of Portland’s most influential families. When it was built in 1914, the grand estate was the talk of the town with its cutting-edge technology that included an elevator, central vacuum system, and thermostat-controlled heating. Today, you can take a self-guided tour of 23 meticulously preserved rooms in the Travelers' Choice Award winner, ranging from a library and sewing room to a Turkish smoking room. Go early if you want pictures of the interiors sans people and be sure to take a look around outside, too. The landscaped grounds boast some of the best views of downtown and the surrounding mountains.

Quote of Sarah saying, “Don’t miss the special exhibitions at Pittock Mansion. When I visited there was an illuminating exhibit about Portland’s Black pioneers in the late 1800s.”

For lunch, hightail it to the Belmont Street outpost of Hat Yai. The casual counter-service restaurant churns out delectable street food including Thai fried chicken and fresh-out-of-the-oven roti. Wash it down with the coconut mango horchata or a boozy tamarind whiskey smash.

To experience more of the city’s Asian influence, the Lan Su Chinese Garden is a must. A peaceful respite surrounded by skyscrapers, the Travelers' Choice Award–winning garden features hundreds of varieties of Chinese plants, pagodas, koi ponds, an art gallery, and a tea house.

After a day of adventuring in Portland, it’s time to get out of town. No car? No problem. From Union Station, it’s roughly a two-hour bus ride to quaint Cannon Beach, OR. Check in to the historic Cannon Beach Hotel, which, despite being on the opposite coast, has a decidedly New England feel. In-room fireplaces, clawfoot soaking tubs, and a whiskey bar just off the lobby up the coziness factor at this Traveler's Choice Award winner. Before calling it a night, dine on oysters Rockefeller, homemade clam chowder, and baby back ribs at Driftwood Restaurant & Lounge, another Traveler's Choice Award winner.

Day three: Wander Cannon Beach

View of Cannon Beach from Ecola State Park, Oregon
View of Cannon Beach from Ecola State Park, OR
Image: Bogdan Bratosin/Getty Images

There are three things you need to know about Cannon Beach’s beloved Lazy Susan Cafe: It’s cash only, there’s almost always a wait, and the oversized scones with marionberries—an Oregon variety of blackberry—more than make up for it.

After breakfast at the Travelers' Choice Award winner, walk to the end of 2nd Street to access Cannon Beach. Admire colorful tide-pool ecosystems and Haystack Rock, a 21-story monolith that’s home to hundreds of nesting birds, from the common murre to tufted puffins. On the walk back to the hotel, pop into one of the many galleries and shops filled with wood sculptures, stained glass, and landscape paintings.

Quote of Sarah saying, “Cannon Beach is not a ‘lay down and have a margarita’ kind of beach like the ones I’m used to, but it’s great for walking, running, or just people-watching.”

Back in Portland, check into The Hoxton Portland Hotel, a Travelers' Choice Award winner, where the vibe is mid-century modern meets industrial loft. Make reservations in advance for the rooftop taco bar, Tope, or snag a sofa at Lovely Rita, where you can keep things simple with the namesake burger and fries or get fancy with the ever-evolving, multi-course tasting menu.

Day four: Appreciate the arts

Frida Kahlo painting at the Portland Art Museum
A selection of pastries at VooDoo Doughnut in Portland, Oregon
Frida Kahlo painting at the Portland Art Museum (L), A selection of pastries VooDoo Doughnut in Portland, OR (R)
Image: Judylyn/Tripadvisor (L), Zack A/Tripadvisor (R)

The Daily Feast, a casual downtown diner, has the perfect fuel for a final day of sightseeing. Post up at one of the window seats for views of the Georgian-style, red-brick Central Library, built in 1913.

A 10-minute walk to the north, you’ll find another literary landmark: Powell’s City of Books. Sprawled across an entire city block with more than a million titles and a cozy coffee shop, it’s safe to say Powell’s is a book lover’s paradise. If you’re looking for something specific, don’t be shy about asking the friendly staff for help—it's a Travelers' Choice Award winner for a reason.

Then, make your way to the Portland Art Museum, another Travelers' Choice Award winner. As one of the oldest art museums on the West Coast, the collection is extensive. If you’re short on time, the Asian art holdings are impressive and highlight the city’s long history of trade with East Asia.

The Crick, Abbey Creek Winery’s urban tasting room, also showcases the convergence of two cultures with a blend of hip hop and wine. The founder, Bertony Faustin, is Oregon’s first Black winemaker and infuses his love of music throughout, from the tastings (called “tracks”) to the live DJ sets featuring up-and-coming artists. Pro tip: Check out their calendar to see if your trip coincides with their popular brunch series.

Go out with a bang with dinner at Lechon, a buzzy South American-inspired restaurant with much-talked-about scallops and margaritas. Reservations at the Travelers' Choice Award winner are recommended or you can try your luck at the bar after 8 p.m. when the crowds start to thin. Afterward, stop into the original location of Voodoo Doughnut. Their creative concoctions double as both dessert and a sweet pre-flight breakfast.

Sarah’s picks

Favorite souvenir: Museum shops always have the best gifts, and the one at Portland Art Museum was no exception. I found a wooden children’s fidget toy that I’ve repurposed into a necklace.

Best place for catching a moment of Zen: As a writer and a reader, one of my favorite ways to relax is to browse bookstores; they’re always so quiet yet stimulating at the same time. I could have spent hours at Powell’s.

Most unique hotel amenity: The Hoxton has custom-designed mugs by local artisans Clay Factor Ceramics. They’re beautiful, useful, and you can buy your own to take home.

One thing you wish you'd known before the trip: If I’d known Cannon Beach was so charming—and had such great art galleries and stores—I’d have stayed an extra night and brought another bag to take home my bounty.

Most interesting person you met: Bertony Faustin’s passion for wine and his drive to make it accessible to everyone is palpable. To know Bertony is to love him!

Where To

Tag along as our Travellers’ Choice winners come to life in curated itineraries.
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Tommie Ethington
Tommie Ethington is a Dallas-based freelance writer. Formerly an editor for Southwest Airlines' in-flight magazine, she continues to write about travel, design and interesting people for a variety of publications including Condé Nast Traveler, Rolling Stone and Texas Monthly. Find more of her work at tommieethington.com.