The Best Oregon Road Trip Itinerary 2024: Exploring the scenic wonder in 7 days

The Best Oregon Road Trip Itinerary

Rugged coastline, refreshing waterfalls, towering mountains and culinary delights. Oregon’s diverse beauty beckons travelers from all around the world to explore it’s incredible wonders. Not only is the western American state known as the beerlover’s ultimate paradise, also it is a highly underrated destination for the perfect US roadtrip. In this comprehensive guide you get the best 7-days Oregon road trip itinerary, carefully curated to showcase the very best must-see destinations of this captivating state. Steal it! 

Text // Cecilie Høgh

journalist

photo // casper janning & Cecilie Høgh

videographer & journalist

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Lean back in the squishy car seat, breathe out and immerse yourself in the embrace of the open road. Imagine pristine alpine rivers and bubbling waterfalls for your eyes, listen to the rhythmic ebb from the mesmerizing, rugged coastline and smell the lust forest filling your nostrils. Traverse the breathtaking scenic highways that crisscross the landscape and enjoy the adventures waiting for you ahead. You just started your roadtrip in one of the most beautiful states in the US, Oregon. The ultimate place for an US roadtrip. Located in the Pacific Northwest region of the United States, bordering to Washington in the north and California in the south, Oregon stands out from other american states in relation to its diverse natural landscape, environmental consciousness, culinary delights and quirky, independent spirit. You can easily say that this place is the brash guy of the US, the one that live on the edges of the conventions, in a good way. Here they praise dreams and the fact of being different. This place is just cool!

Personally we have crossed the US in an RV, visited more than 15 american states and months of experience with American roadtrips and that is why we safely believe that the following roadtrip itinerary for Oregon is the best. In dialog with the tourism organization Travel Oregon and the travel company Pacific Tours, we arranged this Oregon Road Trip itinerary which ensured us the best trip exploring Oregon, and we think you might have too! (You find it below, keep reading) The 7-days Oregon Road Trip itinerary can easily be adjusted and extended with further stops.

Get ready to hit the road and discover the magic of an Oregon Road Trip in only 7 days starting and ending in Portland.

The route: Portland > Waterfalls and nature > Crater Lake > Authentic towns > Oregon Coast > Oregon Coast Beer & Wine tours > Portland.

Day 1: Explore the "Weird" Culture & Drink Craftbeer in Portland

Day 1. As the capital of Oregon, Portland is the perfect place to start and end your Oregon Road Trip. From the Oregon International Airport you find great flight directions to more of the bigger airport in the US and to/from europe too. You will very easily find the pick ups for car rental by following the signs in the terminals and afterwards you only have a short 15-20 minutes drive to the city center of Portland. And you should definitely be excited for this first meeting with Portland! Immediately as you enter the center of Portland you will very likely notice the very unique american culture that abounds in the streets of Portland. A culture you will probably not meet anywhere else. The culture of Oregon is very much marked by the unofficial slogan of the city “Keep-Portland Weird”. What does that mean, you might think? We get it. Read on this Oregon Road Trip itinerary to open up your horizon!

For this roadtrip a rental car is necessary and if you have not booked one yet, we recommend you to book through Autoeurope RentalCars. They collaborate with all the bigger rental car brands like Hertz and Alamo and have cars in all sizes and price ranges.

Book your car for your Oregon Road Trip right here!

Portland Oregon Road trip Keep Portland Weird What to do in Portland

Continued. “Keep Portland Weird” prides itself  on celebrating individuality, creativity and the unconventional. It encapsulates the essence of a city that cherishes diversity and non-conformity. Portlandians take pride in their city’s unique character, celebrate the weirdness that makes it stand out from the crowd. Portland really thrives by nurturing a community that values authenticity and creative expression. So, when in Portland immerse yourself in the vibrant culture and join the locals in celebrating the weirdness that makes Portland extraordinary. For example we recommend to attend the PSAA Street Art Tour to watch the beautiful Street Art all over town and attend local events like the yearly Adult Soapbox Derby event and this was the perfect start to our 7-Days Oregon Road Trip. A chill sunday morning in august we and hundreds of locals met up on the top of a volcano to joust in a soapbox race, and this is how the organizers describe what happened on this typical portlandise sunday on their official homepage.  

“Put down your videogame controller and step away from your Mario Kart. The best way to race is not on a screen: it is down an extinct cinder cone volcano in Southeast Portland”. 

Play Video about oregon portland soapbox derby

Day 1 continued. The homemade soapboxes looked amazing, people were dressed in colorful outfits and people cheered like never before. So so funny. And the most lovely things about it all was when one of the locals dressed like the famous Teletubbies said to us: 

“This is quiet a normal sunday here in Portland”.

Craftbeer & food in Portland

When in Portland on your 7-Days Oregon Road Trip you should also take great notice of the amazing food and beverage scene. Stroll through the trendy Pearl District, indulge in local culinary delights at the buzzing food carts or savoring farm-to-table delicacies at the famous Farmers Markets and really immerse yourselfes in the unique atmosphere that makes Portland an urban gem.
     And one thing you definitely can’t miss is the craftbeer! Did you know Oregon is known as the beer capital of the world? And its for a good reason! In Portland alone you find more than 70 breweries, which is said to be more than any other place in the world. Make some pitstops at the Portlandnise breweries during your exploration and order a so-called “flight” (a small board with more different beers) . Portland is the beerlovers paradise and beer needs to be on your 7-Days Oregon Road Trip itinerary!

We recommend these breweries in Portland

  1. Gigantic Brewer
    Address: 5224 SE 26th Ave, Portland, OR 97202
  2. Breakside Brewery 
    Adress: 1570 NW 22nd Ave, Portland, OR 97210
  3. Wayfinder Beer 
    Adress: 304 SE 2nd Ave, Portland, OR 97214

  4. Little Beast Brewing 
    Adress: 3412 SE Division St, Portland, OR 97202, USA


“Keep Weird” & Drink Craftbeer in 
Portland

Day 2: Highway 138 & The Stunning Waterfalls Oregon

Day 2-3. When you are fed up by the lovely “weird” culture of Portland (if that is even possible), continue your 7-days Oregon Road Trip towards Roseburg and hit the scenic Highway 138 Oregon. The highway of waterfalls! Nestled in the heart of Oregon’s natural wonders, Highway 138 offers a captivating journey through some of the most stunning landscapes in the Pacific Northwest. It is impossible not the feel inner peace when this scenic byway winds its way through the diverse wonder the Umpqua National Forest, pristine lakes, mountains and the most remarkable, cascading waterfalls. Waterfalls is without doubt one of the many treasures of Oregon and one of the things you can’t miss on your Oregon Road Trip so do not skip this on your Oregon roadtrip itinerary.
     We visited in August and experienced surprisingly little peopl (more times we almost got it all to ourself). 

Oregon 7-days road trip Waterfalls Oregon Multnomah Falls
Play Video about Waterfalls Oregon 7-days Oregon Road Trip

Day 2-3 continued. We had such a joy exploring the breathtaking waterfalls along our cruises on our Oregon Road trip and recommend these for the best 7-days Oregon road trip itinerary:

  • Susan Creek Falls
  • Toketee Falls
  • Deadline Falls
  • Watson Falls
  • Multnomah falls (obs: located just outside Portland)
 

The list above with Oregon waterfalls are all quite different and vary in relation to size. Multnomah Falls is without doubt one of the most beautiful waterfalls we have ever seen due to the high of 183 meters. This makes it the tallest one in all of Oregon, but definitely also the most touristy one.  We recommend to spend at least an hour or two each place to deeply take in the views and the pure silence from the nature (at the smaller waterfalls at least). These visits are some of ours most memorable from your Oregon Road Trip. 

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Day 2-3 continued. We recommend to end your waterfall-exploring-days in one of the hotels or campgrounds along Highway 138. We stayed at SteamBoat Inn by the north Umpqua river this night and it was one of our most unforgettable ones ever. We got our own little cabin with direct connection to a balcony by the river and were  located deep in the forest, far away from everything else than waterfalls and pure nature. Without signal and internet this stay were earmarked relaxation and sumptuous food as the restaurant serve all organic and local cultivated food without mentioning the wine. So delicious.

You could spend the night at one of these accommodations along or near the Highway 138 

 

“Where to stay near the Oregon Waterfalls?”

Day 4: The 7 Wonders' Crater Lake

Day 4. Depending on where you choose to spend the night, the next morning you should continue your 7-Days Oregon Road Trip route along Highway 138 and explore more beautiful waterfalls. And then, set your course toward Crater Lake. This is a must-see when in Oregon and definitely a destination deserving a prominent spot on the list for your Oregon Road Trip! The drive itself is a just as captivating as the destination for all nature enthusiast and adventure seekers alike taking you through the Crater Lake National Park. Nestled in the heart of the Cascade Mountains the drive winds its way through forest and peaks providing you with the most breathtaking views.
   Arriving at Crater Lake you will be greeted by a mindblowing sight. Formed by a collapse of an ancient volcano more than 7700 years old, Craker Lake is the deepest lake in all of United States. It is 592 meters deep and has the most crystal-clear waters. So clear it is often refered to as the purest in the word.  It is so beautiful that it has been chosen of one of The 7 Wonders of Oregon.

Day 4 continued. When at Crater Lake you can take the Rim Drive for a 53 kilometers long scenic road encircling the lake, go for a hike at the trails or enjoy the views from the Crater Lake Lodge. It is also an option to go for an boat tour to Wizard Island. We had a lovely lunch at the Crater Lake Logde – a premier fine dining with Oregon-grown ingredients. Remember to book in advance. Exploring the enchanting beauty of Crater Lake on your 7-Day Oregon Road Trip will be visit you will never forget. We would have loved to spend a night at Crater Lake Lodge, but already had made an reservation in the small  town Prospect 28 miles from Crater Lake.  We checked in at the Historic Prospect Hotel, spent the early evening exploring the nearby Natural Bridge and Rogue River Gorge and ended our day with the signature hand carved prime rib at the Hotel’s Dinner House – fine dining in a relaxed atmosphere. This was a very authentic stay in a very small, almost ghosttown, but we enjoyed every second and really felt the history of the place in the atmosphere. We imagine staying at the Crater Lake Lodge is more touristy, but with a better view for sure. Book as soon as possible no matter what you prefer.

Day 5: Explore the Oregon Coast, Sealions & Horse-riding

Day 5. Leaving the natural wonder of Crater Lake, the vigouros forrests and national park, today the course is set towards the Oregon Coast to make this the complete, best 7-Day Oregon Road Trip itinerary. The coast is another must-see in Oregon and you should be very excited. Stretching for over 584 kilometers (363 miles) the Oregon Coast impress with its pristine beaches, cliffs and charming coastal towns. Expect sealions, whales, wineries, remote beaches, dunes and the most breathtaking views to the beach from the roads. Broadly, the Oregon Coast consists of 3 regions and all of them have their own unique feel and landscape and for that reason we recommend you to spend as many kilometers along the coastline as possible. Now lets talk about where to go on the Oregon Coastline for your 7-days Oregon Roadtrip. Read on! 

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Day 5 continued. For the best Oregon Road Trip with a 7-days itinerary you should drive towards the central coast and New Port, but make you first stop of the day in the coastal town of Florence and make your first encounter with the coast of Oregon by horseback. We went for a beautiful Horseride on the beach in Florence with C&M Stables and it was absolutely delightful. Feel the warm salty air against your cheeks and enjoy a magnificient view of the coast while your horse stroll slowly though the waves the waterline. What a first meeting! It’s very familyfriendly so everyone can join this adventure. 
     Have a late lunch or dinner in Nye Beach in Newport afterwards, wander the streets of the coastal town by feet, take in the historic architecture and go for a dip in the ocean. You should also visit the bayfront and say hi to the many Sealions hanging on the stones – at least you will smell that you now is located in the heart of a fishervillage. New Port call itself the “Dungeness crab capital of the world”. End your day 4 on your 7-Days Oregon Road Trip on one of the seafront hotels and digest the impressions so far. 
     If you choose to lengthen your Oregon Road Trip itinerary for more than 7-Days you could also first drive to the south coast of Oregon to Charleston and go fishing, paddling or golfing or explore the Samuel H. Boardman State Scenic Corridor. Such lovely places!

 

 

We recommend these accommodations in New Port for night 5

 

“Where to stay at the Oregon
 Coastline?”

Day 6: Oregon Coast Beer- & Winery Tours

Day 6. As claimed Oregon is said to be the Beer Capital of the world. In Oregon alone you find more than 200 breweries and brew pubs with a large variety of beer. For more than thirty years the brand Rogue Ales & Spirit has been at the forefront in the booming beer industy and actually they are having their headquater in Newport. Just look for the big red silo. Even if you are not interested in beer a visit or guided tour here will be interesting. It is open every day and the public tours are free. Inside the Rogue World Headquarter you will also find the two-story brewpub with a view to the Yaquina Bay and the picturesque marina. You could also enjoy your lunch in here and try some of the 40 different Rogue Ales and lagers on tap. They also have a retail shop with lots of merchandise and beers to go. Overall such an authentic experience.  We had a talk to the chef master and if you are interested in hearing what we said you should click the play button at the video below.  

Play Video about Beer Oregon Brewery Rogue Ales Headquarter Roadtrip

Day 6 continued. From beer and breweries, the rest of the day on your Oregon Road Trip should be spent on another Oregon specialities within beverage. Can you guess it? Wine, of course. The Oregon wine region has become famous for its high quality Pinot Noir and overall you will find lots of delicate wines. Reach Route 101, known as the Pacific Coast Scenic Byway, drive north and enjoy the beautiful views of the ocean, forest and mountains of the Oregon Coast until you reach the town Otter Rock. In this little town, perched on a cliff high above the Pacific Coast  is waiting Oregon’s most unique boutique winery named The Flying Duchtmann Winery. It is the only winery on the coast and through the years this winery has earned a high reputation for consistenly producing wines of distinction. 

Play Video about Oregon Wine Flying Dutchman Winery Roadtrip

We had a very interesting chat about the wines and tried more different before we ended our tour in the lovely backyard with the most impressive view to the Oregon Coast. On a bench high above the coast we sat for an hour enjoying a glass of our favorite wine from the winery and enjoyed an unusually beautiful view of the sea. Suddenly the most amazing thing happened to us. Two whales appeared in the horizon and we certainly had to pinch ourselves for a while not to take off from pure euphoria.  This experience we will never forget!

Day 7: Back to Portland & Departure

Day 7. From craftbeer & “weird-culture-life” in Portland, to stunning waterfalls and vigorous nature at the Umpqua river and Crater Lake, to wine tasting and coastlife at the Oregon Coast, your 7-days Oregon Road Trip itinerary has come to an end. If you are planning to leave Oregon after these days it is now time to hit back to Portland to reach the airport and hand in your rental car, or maybe you found out you need to go back and explore some of your favorite places once again? Don’t worry, we get it. 
     As you might be aware of now, Oregon has so much to offer and you can easily extend your 7-Days Oregon Road Trip itinerary if your time allows it. We especially recommend more days in Portland in the beginning of your trip to get to know the Portlandise culture even more but also to get over any jetlag you might have before heading the road. Also you can spent lots of time exploring the coastline not to mention the incredieble nature. Beside Crater Lake, Oregon’s 7 Wonders also include “The Painted Hills” and the “Smith Rock” between others which are also very very scenic to explore, and we highly recommend these too.
     If you are about to plan you Oregon Road Trip do not hestitate to comment this blogpost  or simply enter the°travelers’club and ask/find the answers you are looking for in relation to Oregon – all questions are welcome! .. And you might even connect to fellow travelers planning the same, win win. Lastly, you are very welcome to go to our Instagram where you probably will find further inspiration and helpful information for your planning to Oregon. 

.. btw watch our full travel video guide from Oregon below and do not hesitate to check out out Youtube channel for more travelinspiration.  

Until next time,
Safe Travels

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