: Sean Pavone / Alamy Stock Photo

Road Tripper’s Guide to the Portland Region

August 12, 2021 (Updated August 20, 2021)

Editor’s note: Face coverings (ages 5 and up) are required at all indoor and outdoor public spaces statewide, regardless of vaccination status. Learn more here.

In Portland the vacation vibes can switch between climbing mountains and window shopping in the city at the snap of a finger — or a turn of your car’s ignition. You can be exploring waterfalls and dog-friendly trails in the morning and tasting wine, kiteboarding or spotting gray whales in the afternoon. 

You can do all of this because parts of the Oregon Coast, the Willamette Valley and the Columbia River Gorge region are within an hour or two of Portland. So if you want to explore the broad diversity of attractions and landscapes Oregon has to offer — but don’t quite want a long road trip — you can still experience the best of all worlds by making your base camp in downtown Portland. 

With so many Hilton Hotels in the Portland area — all with ample parking options and convenient public-transit access — you’re spoiled for choice in the accommodations department. Here’s what to do if you have a few days to explore the Rose City and beyond.

Furry friends are welcome at The Duniway in downtown Portland, where you'll find food, drink, arts and culture and sporting events all within blocks.

Downtown Portland

The Embassy Suites near Old Town Chinatown is home to Mother’s Bistro, which serves a hearty brunch menu and Italian comfort food throughout the day. It’s also walking distance from the tranquil Lan Su Chinese Garden. On weekends in the summer, the area buzzes with outdoor street vendors from the Portland Saturday Market, which features hundreds of local small arts-and-crafts businesses and artisans.

Canopy is a great place to gather with friends and is located in the heart of the Pearl District. Grab lunch at nearby Republica PDX, which serves modern Mexican cuisine, before diving into your day’s activities — whether it’s biking (grab a BIKETOWN bike) along the Willamette River at Tom McCall Waterfront Park or browsing charming shops like EcoVibe, Reclamation or Coral Story Beauty

The Duniway, named after Oregon suffrage champion Abigail Scott Duniway, has a vibrant, youthful vibe and is pet friendly for anyone traveling with their furry family members. Situated downtown, you can easily catch a Timbers or Thorns game at Providence Park. Finish the night with dinner at Habibi Restaurant for traditional Mediterranean cuisine, or stroll down to the 5th Avenue Food Cart Pod to indulge in Portland’s beloved street-food scene. Unwind with a glass of wine or cocktail at the long chef’s bar at Southpark Seafood before tucking in for the night.

A two-tiered waterfall flows over a mossy cliff
Wahclella Falls is a short drive (or shuttle ride) away from Portland. Visit midweek to see less crowds and get that sweet photo opp. (Photo by Arpad Jasko / Alamy Stock Photo)

Columbia River Gorge

If you head east from Portland along Interstate 84 toward Mt. Hood, you’ll reach the Columbia River Gorge. While you’ll definitely pass dozens of gorgeous waterfalls, Wahkeena Falls has a great paved trail for all ages and skill levels with less foot traffic than some of the more popular spots. To skip the hassle of driving and parking, consider traveling to the Gorge without a car. It’s a breeze to tour the region’s iconic attractions via a shuttle ride from Sasquatch Shuttle, Gray Line Trolley or the Columbia Gorge Express. (Psst: If Multnomah Falls is on your bucket list, hop on a shuttle or book an advance ticket, required through Sept. 9, 2021.)

If you’re looking to do something a bit more extreme, the Gorge is ranked one of the top sites in the country for kiteboarding. Even if you’ve never done any kind of water sports, taking a lesson with Cascade Kiteboarding will make sure you are comfortable, safe and having fun.

For a quick bite, stop by one of the many casual eateries Hood River for the best lunch spots in the Gorge, or sample the fresh seafood at the Native-owned Brigham Fish Market in Cascade Locks. During the warmer months, fresh farm stands, U-picks, wineries and cideries are open along the Hood River Fruit Loop, and you can pick your way through the juiciest berries, pears and apricots on family-run farms. If you have time to drive another hour or so, consider heading east of Hood River for more tasty (and less-crowded) adventures on the East Gorge Food Trail

Watch for spouting whales from the trail at Ecola State Park. Consider leaving the driving and parking to someone else by taking public transit to the Coast. (Photo by Joni Kabana)

Oregon Coast

Heading northwest from Portland, cinephiles should stop in Astoria, where movies  like “Free Willy,” “The Ring Two” and “The Goonies” were filmed. You can stop into the Oregon Film Museum and spot your favorite film sites along the Oregon Film Trail. Find plenty of fish ’n chips, clam chowder, craft breweries, boutique shops and amazing views of the Columbia River. 

(If you prefer, you can leave the driving to someone else. Columbia County Rider offers daily bus service from Portland to the town of Rainier, where you can connect to a Sunset Empire Transportation District bus to Astoria. NorthWest POINT also offers daily bus service from Portland to Astoria, via Cannon Beach and Seaside.)

South of Astoria and about one hour west of Portland, Seaside is one of Oregon’s most iconic beach towns with unique attractions for every activity level. Seaside marks the end of the Lewis and Clark trail, and the downtown area is packed with family-focused shops for candy, toys and ice cream. Fun-seekers of all ages can check out the Funland Arcade, Highlife Adventure Park and the Inverted Experience. Walk or bike along Seaside’s famous Promenade, which celebrates its centennial anniversary in 2021.

Wind down from the action at Ecola State Park, where you can explore the 2.5-mile Clatsop Loop Trail or bring your binoculares to try to spot migrating gray whales during winter and spring months. 

An hour south of Ecola State Park is the town of Tillamook, best known for the Tillamook Creamery and their dairy-based products that you can sample on-site. Find all of the best coastal fare and farm-based experiences along the North Coast Food Trail, which stretches from Astoria to Tillamook. 

You don't need to be a serious wine drinker to appreciate the beauty of the vineyards in the Willamette Valley.

Willamette Valley

Before you wrap up your Portland-based adventure, head down to the rolling hills of the Willamette Valley. Book a stay at the Embassy Suites Washington Square for quick access to wine country. Vino lovers will enjoy sampling some of Oregon’s finest wines at Bells Up Winery or Niew Vineyards, both in Newberg — just under an hour southwest of Portland. If you’d like to sit back and enjoy a curated wine experience by a local expert, you can skip the planning and book a private tour with Dirty Radish, which highlights small boutique wineries that promote diversity, sustainability and organic growing practices. 

Aside from wine, you can also tour some of the small towns tucked in the valley. Salem, the state capital, is rich in both history and incredible food. Stop by Epilogue Kitchen for a sit-down restaurant or opt for variety at The Yard Food Park. Check out the Mid-Willamette Valley Food Trail for more great eats and farm-based experiences in this part of the valley. 

About The

Kay Kingsman
Kay Kingsman is a travel blogger based in Portland and the voice behind The Awkward Traveller blog. When she’s not recounting her hilariously embarrassing adventures abroad, Kingsman uses her platform to provide tips and information to make travel more accessible and attainable. She’s featured in Forbes, Buzzfeed and Dame Traveler.

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