On the Road in Oregon: An 8 Day Itinerary

Oregon truly has it all. Crashing waves, majestic tidepools, famous beach rocks and sunken ships all make the coast a must-do trip. But, there’s much more to Oregon than the coast. The innards of the state also boasts lush forests, jaw-dropping waterfalls, big mountains and winding rivers. Today we’re sharing our 8 day road trip itinerary exploring most of the beauty this must-see state has to offer. Happy trails!

Day One: Bend

We kick off our trip in Bend; an outdoor recreation hub with a solid food and beer scene. No matter the season, there is adventure to be found here. Even 10 days in this little playground alone might not be enough. During the winter, nearby Mt. Bachelor ski resort won’t disappoint. You can then explore Umpka Hot Springs to warm you up after a day on the slopes. During the summer paddleboarding at Elk Lake, hitting the Lava River Caves, or a visit to Tumalo Falls or Smith Rock gives you ample adventure opportunities.

No matter the recreation you choose, Bend’s stellar foodie scene hits the spot after working up an appetite. Spork and The Brown Owl are good choices for grub. For drink try Deschutes Brewery, Atlas Cider or Humm Kumbucha. Something for every taste. With Day One in the books, It’s time to crawl into your campsite at Tumalo State Park. Tumalo is equal parts amenities, equal parts rustic. This is the perfect place to rest your head after a day of adventure.

Day Two: Ashland

On your four hour commute to Ashland, make a pit stop to stretch your legs at the infamous Crater Lake. A must-see National Park when exploring Oregon. Be prepared for a wave of wild, artistic culture as you enter into the quaint, small town. Do not miss a jaunt through Lithia Park, which offers 100 acres of green space smack dab in the middle of town. With its many festivals and live music events offered throughout the year, finding something to do here is easy, despite it’s small size. Fill your belly at Martolli’s, a no brainer pizza joint where the ingredients are local and the sauces are homemade. End your night with a sweet treat from Zoey’s Cafe & All Natural Ice Cream. Finally, rest your traveling bones at one of the local yurts or safari tents for nightly rent in the area.

Day Three: Sunset Bay

Trade your hiking boots for your bathing suit because you’re headed to the coast today. In just over three hours, you’ll find yourself at Coos Bay - a gateway town to jaw dropping coast lines, lush forest and loud sea lions. Make your way to Sunset Bay State Park where you can chase waves, share a picnic and soak in the sun. Travel South along the coast to spot sea lions and discover endless sea creatures in secret tidepooling holes. Snag some fish & chips from the local hole-in-the-wall called Monkey Business before returning to your campsite at the water’s edge.

Day Four: Newport

In a little less than three hours, you’ll arrive at your next destination. A quintessential coastal town lined with colorful shops, more sea lions than people, and Mo’s- the best clam chowder in the state. Depending on the weather, there are a couple of ways to experience Newport. If the sun is shining, take your adventures outside to the Devil’s Punchbowl, drive over the Yaquina Bay Bridge or go out to the Yaquina Lighthouse. For inside options, the Oregon Coast Aquarium is a perfect way to spend your day before spending the night at one of the endless oceanside cottages for rent in the area.

Day Five: Cannon Beach

Cannon Beach is a short two and a half hour drive from Newport. Grab a delicious breakfast-to-go from Cannon Beach Bakery before heading straight to Haystack Rock, of Goonies fame. Explore the tide pools and discover alien-colored sea life for hours. From there, make a pit-stop over at Hug Point for beautiful waterfalls and mysterious sea caves before filling up with craft beer at Pelican Brewery. End this epic day with a good night’s sleep surfside at Ecola State Park.

Day Six: Portland

Before leaving the coast for good, make one last stop to explore the shipwreck of Peter Iredale just outside of Astoria. Getting into Portland, make sure to grab an out-of-this-world donut at Blue Star. Next up, take a stroll through Powell’s City of Books, the largest used book store in the world, or soak in some green space at the Japanese Garden. Fill your evening with a brewery tour at Base Camp Brewing and then wind down watching the sunset at St. John’s Bridge.

Day Seven: Mt. Hood

With the city in your rear view, it’s time to get back to some outdoor adventures. First up, hike to the top of Multnomah Falls, the largest falls in Oregon before your stopover at Mt. Hood. After a morning of hiking, change it up with a warm soak at Bagby hot springs. From there, SUP the beautiful Trillium Lake before heading off for some scenic wine tasting and locally-sourced food at Field & Vine Dinner. Spoil yourself with a night of rest at the Sandy Salmon Bed and Breakfast.

Day Eight: Joseph

The last leg is a rewarding drive of four and a half hours. Referred to as the Swiss Alps of Oregon, Joseph is a serious gem of a small town. Spend some time exploring the breathtaking Eagle Cap Wilderness. From glacial lakes to meadows full to the brim with wildflowers, you’ll be glad you did. Now that you’ve worked up an appetite, it’s time for a cold beer and a damn good burger at Terminal Gravity Brewing. Your final destination is at the historic Jennings Hotel. But, don’t forget to grab a sweet treat from Arrowhead Chocolates on your way out of town. A reward for an adventure well done.


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Now gear up and get out there!