You are here

A Guide to Doing a Road Trip in Oregon

Cannon Beach, Oregon

Road trips through the USA are the perfect way to get out and discover what this diverse country has to offer, and Oregon is no different. I spent two weeks on a road trip around this coastal state, covering everything from Portland to Mount Hood. Here’s my suggested itinerary if you’re looking to do the same.

Portland - Image: Alex Champion


Image: Alex Champion


Start your journey by flying into the vibrant city of Portland, renowned for its culinary scene, cultural offerings and tax-free shopping. Make sure you check out the legendary Powell’s City of Books (the largest new and used bookstore in the world), the Portland Japanese Garden, and the International Rose Test Garden. You can even treat yourself to a great view of the city from the Willamette River on a Portland Spirit Cruise. Are you a foodie? Then be sure to book yourself onto a Forktown Mississippi Walking Food Tour and pop in for a beer at the Ecliptic Brewery to wash it all down with.

Cannon Beach, Oregon

Cannon Beach, Oregon

Cannon Beach

Pick up a car in Portland and take Highway 26 until you reach Cannon Beach on the coast. This charming seaside town is home to lots of pretty cafes and boutiques and the landmark Haystack Rock. Head up to Ecola State Park for a great view of the Oregon coast and opportunities for hiking and surfing. Love craft beer? Make sure you grab a drink at the Pelican Brewing Pub before you leave.

Oregon Coastline - Image: Alex Champion

Oregon Coastline

Image: Alex Champion


Make your way down the coastline to Florence, stopping in at the popular Tillamook Cheese Factory. There are many viewpoints along the way offering panoramic vistas of the beautiful Oregon coast. Next, visit the Sea Lion Caves, which are home to a great number of Steller sea lions.

Crater Lake

Either take the coastal route or stop in at Eugene for a spot of lunch before making your way to the stunning Crater Lake. This spectacular blue lake is the deepest in the United States and is a must-see on your Oregon road trip. Trust me, you won’t regret the drive to see this iconic landscape.

Crater Lake

Crater Lake


From Crater Lake, head north up to the town of Bend, often referred to as “the outdoor playground of the west”. After getting adventurous with activities like rafting, hiking or biking, make sure you check out the great restaurant and bar scene. Take a day trip out to visit the unmissable Smith Rock State Park and, if you’re feeling particularly energetic, hike to the top for incredible 360 degree views.

Baker City

It’s a long drive to Baker City, so break up the day by stopping at the striking Painted Hills (one of the Seven Wonders of Oregon) and Fort Rock. Once you’ve arrived, indulge yourselves in some local food and drink on a Walk & Taste Tour to get a flavour of the city.

Views in Oregon - Image: Alex Champion

Views in Oregon

Image: Alex Champion


Head northwest through Wild West country to Pendleton, which boasts a rich tradition of fine craftsmanship, including a selection of fascinating stores selling handmade leather saddles, boots, cowboy hats and much more.

Ponzi Vineyard - Image: Alex Champion

Ponzi Vineyard

Image: Alex Champion

Mount Hood

Finally, make your way west via Mount Hood. Love winter sports? Stop off for some skiing or snowboarding at the impressive Timberline Lodge (grand hotel featured in The Shining) or just enjoy a drink overlooking the beautiful surrounding slopes. Stop off at the gorgeous Multnomah Falls before concluding your trip back in Portland.

Written by Alex Champion

I'm a lover of the outdoors and am always looking for that next big adventure. You're more likely to find me hiking in a National Park than lying on a beach!

More articles from this author >

Feeling Inspired? Chat to our Lovely Travel Consultants Today!

Flight Centre’s Travel Consultants really know their stuff when it comes to creating bespoke itineraries. Get in touch below, and let us tailor-make it easy