Does anyone remember playing The Oregon Trail computer game in computer class? Growing up, that’s about the only connection that I ever had with the state of Oregon.

Little did I know that many moons later, the Pacific Northwest would be a huge must visit destination on my travel bucket list.

We love road tripping in new destinations and I have to say, Oregon was absolutely INCREDIBLE for a road trip!

With such a variety of landscapes in Oregon you can have a new discovery every day: from city life to rural farms, exploring epic waterfalls and adventures along the Pacific coastline.

There is literally something for everyone in this friendly state. The very magical Oregon absolutely needs to be on your travel bucket list!

I’ve created the perfect 7 day itinerary for your Oregon road trip where you get to see SO MUCH of this beautiful state – be sure to save this for your future travels 🚙🏔️💦⬇️

The perfect 7 day itinerary for your Oregon road trip

How to get to Portland

The easiest way to get to Portland is to fly to Portland International Airport (PDK). There are direct flights from London to Portland and it’s ONLY 9 hours 50 minutes to get halfway across the world!

And once you land at the airport, it’s seriously RIGHT in Portland! From Portland International Airport it’s a 15 minute drive into the centre.

Car Rental in Portland

Renting a car from Portland Airport couldn’t have been easier. I’d recommend booking your rental car ahead of time via Discover Cars, we use this when I travel as you can easily find the best prices from rental car companies.

We rented a car as we knew we wanted to road trip around and explore after spending a few days in Portland. I will note that we were recommended not to leave any belongings overnight in our rental car as unfortunately in the city centre there can be break ins. So we just took everything into our hotel room.

Alternatively, you can an Uber or a taxi directly to your hotel in Portland which is equally super easy as it’s such a short drive to the centre.

Public Transport in Portland

There are plenty of ways to travel around Portland without renting a car.

In addition to car and ride share services, the city also has a public transportation system that includes bus service, the MAX Light Rail and a streetcar, these cost from $5 per day for adults. There’s also the option to rent a bike or electric scooter or of course, walk.

Days 1-2: Portland

Alright, after our 15 minute drive into the city – We’re kicking off our road trip with a few days in the eclectic city of Portland.

I’d really recommend this as a start and end location for your Oregon trip as Portland have a great international airport, Portland International Airport (PDX). You can pretty much fly in here from anywhere!

📚 Powell’s Books, buy everything!

Start your morning with a visit to Powell’s Books. Did you know it’s the world’s LARGEST independent used and new bookstore?

It takes up an entire city block and houses up to 1 million books! I spent so much time here and picked up a few books to take home. I wish I could have bought so much more, but alas, a limited suitcase!

They also have a coffee and treats shop within the store. Buy some books and then enjoy your spoils with a coffee and tasty pastry.

🥀 Portland International Test Rose Garden

Next up is a visit the International Rose Test Garden located in Washington Park.

It’s free to enter but you’ll pay for street parking nearby. It’s beautiful there are over 10,000 rose bushes here!

When to visit? The roses are in bloom from May-October so it’s helpful to know when trip planning if you’ll see them or not. We visited in August and there were so many! Though my guess is June/July would be the best.

🍻 Beer at Prost Marketplace

Head for a pint and lunch at Prost marketplace!

It’s giving very European pub vibes with a Portland twist – we loved it here, everyone was so friendly.

Also, I pretty much order a giant soft pretzel anywhere that has them on the menu. So I definitely recommend getting one of those.

🌮 Por Qué No? for tacos

There are two of these delicious Mexican restaurants in the city.

I’d highly recommend a delicious visit to Por Qué No? for tacos. These were made super fresh and we sat outside in the sunshine to enjoy them.

I can only assume the margaritas are killer too – but we had a lot to see that day so opted for cokes!

🌃 Revolution Hall rooftop for drinks overlooking the city

This is such a cool spot and definitely one locals love, we went with our friends who live here. Get there early to grab one of the best tables!

🚡 Aerial Tram at sunset

Something cool and unique to do is to get tickets to go on the Portland Aerial Tram at sunset.

A round trip ticket costs $8. Maybe not one those who fear heights – but I promise, it’s not that scary! 

We got there a little before sunset so had time to take it all in. Can you spot Mt Hood in the distance? 

Also there’s not really much to do at the top – it brings you to the top where the hospital is. So this one is essentially something JUST for the view.

🏰 Witch’s Castle

Just a 10 minute drive outside of the city and you’ll find yourself surrounded by woodland.

There are some great hiking paths to explore… and one of those will lead you to the Witch’s Castle.

During parts of the year it is covered in moss which in my opinion looks better than the graffiti but Portland’s motto is after all, “Keep Portland Weird” so moss or graffiti, it’s still a cool famous spot to see in the city.

💤 Stay The Hoxton (great rooftop bar here too!)

We stayed at The Hoxton Portland during our visit to the city, which we loved. They have great interior aesthetics and the staff couldn’t have been nicer.

They also have a beautiful downstairs bar and lounge as well as a super cute rooftop bar called Tope, serving up tasty Mexican food and YES I can confirm the margaritas were excellent.

PS If you’re driving, I really would recommend splurging on the valet parking too.

We were recommended at the airport rental to not leave anything in our rental car overnight in the city as well. Portland is a beautiful city but there are some issues with drug addiction and homelessness through the city to be aware of.

Day 3: Columbia River Gorge

Wake up in Portland and get ready to hit the road. Grab coffees, doughnuts, pastries first, of course!

Check out of your hotel, we’re heading east. A 30-minute drive outside of Portland brings you to the Historic Columbia River Highway.

🚙 Driving the Historic Columbia River Highway (30 mins from Portland)

This is a beautiful journey and one you really will want to add to your trip.

The Historic Columbia River Highway is famous as home to some of the best waterfalls and scenery. To think it’s super close to such a major city – it’s a huge bonus in my eyes!

🔭 Portland Women’s Forum Scenic Viewpoint

Start your journey by stopping off at the Portland Women’s Forum Scenic Viewpoint.

I think this is a place that is definitely overlooked as it’s the initial start of the Highway.

But this spot has the best views of the Vista House Crown Point. There is parking readily available and you simply hop out of your car and look out across the gorge – it’s gorgeous!

💦 Latourell Falls + 💦 Multnomah Falls

Don’t miss these super easy to get to falls.

I honestly love scenic points like this because they are RIGHT by the car parks. It makes them accessible to wander up to and explore if you are tight on time as well.

I would recommend getting up early to visit Multnomah Falls though. It can be a very busy spot.

We arrived fairly early – if you arrive before 9am – parking is free.

Though I’m not sure how long you can leave your car there. We got out before 9am hit! Otherwise you do have to reserve parking at timed slots throughout the day.

🍷 Hood River Wineries

Did you know that Oregon is becoming famous for their wineries? They make really good wine! I highly suggest visiting wineries around the state. You can find them located all over, but we drove to Hood River to explore the wineries there.

We popped into Stave and Stone for a few glasses of wine to enjoy. Well, I enjoyed a few while Joe enjoyed responsibly as he was driving.

🏔️ Bonus points: Trillium Lake for sunset

This truly was a bonus of the night for us! We weren’t sure if we were going to have time to do this or not… but we ended up going! We drove to Trillium Lake from Hood River to catch a most spectacular sunset.

It is absolutely stunning at sunset, but I suspect a sunrise from here would be a dream to see as well.

Once again, it’s very easy to park here. But be weary – reception is a little spotty, so make sure you save directions ahead of time.

😴 Stay overnight near/around Hood River – I’d really recommend the Best Western Plus right on the river.

Day 4: Astoria / Oregon Coastline

Start the day with a slow morning at your hotel! The Bridgeside Restaurant for breakfast was actually SO good at the Best Western and with the setting I kind of felt like I was in the Twilight films.

Next up? Drive from Hood River to the coast. This is a 2 hour and 20 minutes drive.

Pop along to Astoria! This seaside town is so cute and is well worth spending a relaxing afternoon here. The Goonies was actually filmed around here too.

🍽️ Astoria Brewery is a MUST for lunch and a pint.

🚙 Drive and stay near Cannon Beach or Seaside

🪨 Bonus points! Explore Ecola State Park or Cannon Beach for sunset

Day 5: Oregon Coastline and Eugene

Welcome to the coast of Oregon!

Let’s head to Ecola State Park Viewpoint which overlooks Crescent Beach, Chapman Beach and way down at the end, Cannon Beach. But we’ll get there shortly!

This is one of the BEST viewpoints of the beaches and did you know that they actually filmed The Goonies here?

Pretty cool, right?

And only a ten minute drive away is Cannon Beach!

The best entrance is down this scenic pathway that leads directly out to Haystack Rock. 

You can usually see The Needles rock formations next to it, but on foggy evenings and mornings, it’s a little tricky! 

But that’s what makes the Pacific Northwest so downright magical.

Start your day with breakfast in Seaside at Osprey Café – one of the best breakfasts ever!

🚙 Drive down the coastline

🍗 Stop for lunch in Yachats at Big Dog BBQ – SO GOOD!

🔨 Visit Thor’s Well and the Heceta Head Lighthouse

💤 Drive to Eugene and stay at Graduate Hotel Eugene, sports fans will love it and interior decor fans will too!

Day 6: Waterfalls

This is a day all about waterfalls!

These waterfalls will differ from the Historic Columbia River Highway! These ones are a bit more of a hike to explore.

🥾 Proxy Falls

This one is kind of a hike but it is WORTH IT.

And it can be a little confusing to find so stick to reading the sign posts.

You will probably feel a little lost at some points but carry on… you’re doing the right thing! And this journey was well worth it. This also was one of the scariest photos I’ve taken!

I actually fell off of the log and into the water – it doesn’t look very high and really isn’t… but it was kind of scary. So please be cautious when doing stupid things to get the shot like me!

💦 Koosah Falls

Now this one is also luckily close to the car park. And this waterfall is so beautiful!

After my mishaps at Proxy Falls, I wasn’t too keen to do much more for the day. But I am so glad we stopped here.

💙 McKenzie River and the Blue River are near here too!

💤 Back to Eugene for the night – rest and relax at your hotel, you’ve earned it!

Day 7: Bonus day! 

☕️ Enjoy a slow morning before going to the airport

🚙 Eugene back to Portland is about 1 hour 45 minutes drive

✈️ Fly home and reminisce about your amazing memories!

I hope you found this seven day itinerary for a road trip around Oregon helpful! This is one of the best trips that we’ve ever been on. We saw so much – and yet only scratched the surface of the amazing Oregon.

Someday we’ll be back!

Kelly xox