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 by fast forwarding many moons later, the Pacific Northwest would be a huge must visit destination on my travel bucket list.
As I got older and started to pay more attention to the beauty found in travel… I always knew that I’d want to travel along an epic road trip around Oregon.
We love road tripping in new destinations and I have to say, Oregon was absolutely INCREDIBLE.
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 even 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 too!
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
Portland Days 1-2
We’re kicking off our road trip with a few days in the city of Portland.
I’d really recommend this as a start and end location as they have a great international airport at PDX, so a great idea you can always do is to mix these activities in the city for start and end points.
📚 Powell’s Books, buy everything!
A MUST thing to do is visiting 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.
🥀 Portland International Test Rose Garden
Next visit the International Rose Test Garden located in Washington Park.
It’s free to enter but you’ll pay for parking nearby. It’s beautiful there are over 10,000 rose bushes here!
PS the roses are in bloom from May-October so it’s helpful to know when trip planning if you’ll see them or not.
I think this is a pretty great chunk of time in the year. 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 or two at Prost marketplace!
It’s giving very European pub vibes with a Portland twist – we loved it here, they were so friendly.
Also, I pretty much order a giant soft pretzel anywhere that has them on the menu. So you know, I definitely recommend getting one of those.
🌃 Revolution Hall rooftop for drinks overlooking the city
This is such a cool spot and definitely one for locals to frequent. Get there early to get the best tables!
🌮 Por Qué No? for tacos
There are two of these fun 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!
🚡 Aerial Tram at sunset
Get tickets for 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?
🏰 Witch’s Castle
Just a 10 minute drive outside of the city and you’ll find yourself surrounded by woodland.
There are some pretty 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 spot to see.
💤 Stay The Hoxton (great rooftop bar here too!)
We stayed at The Hoxton Portland during our visit to the city, which we loved.
Really great aesthetics and interiors 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 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 issues with drug addiction and homelessness through the city. Just a precaution of city life but I thought I’d share with you too!
Columbia River Gorge Day 3
Wake up in Portland. Grab coffees, doughnuts, pastries first, of course!
Check out of your hotel and head 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 has 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 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! (Sorry – had to do it)
💦 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 pretty accessible to wander up to and explore if you are tight on time as well.
I’d 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 actually have to reserve parking at timed slots throughout the day.
🍷 Hood River Wineries
You’ll find Oregon is rapidly famous for their wineries!
And Oregon makes 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 drove to Trillium Lake from Hood River to catch a spectacular sunset.
It was 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.
Astoria / Oregon Coastline Day 4
🥞 Start the day at your hotel! The Bridgeside Restaurant for breakfast was so good
🚙 Drive from Hood River to the coast (2 hours 20 mins)
⚓️ Pop along to Astoria! This seaside town is so cute and is well worth spending a relaxing afternoon here.
🍽️ Astoria Brewery for lunch and a pint
✨ Walk around the town
🚙 Drive and stay near Cannon Beach or Seaside
🪨 Bonus points! Explore Ecola State Park or Cannon Beach for sunset
Oregon Coastline and Eugene Day 5
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!
Waterfalls Day 6
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 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 but it was kind of scary. So please be cautious when doing stupid things to get the shot please!
💦 Koosah Falls
Now this one is also luckily pretty 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 – It’s a 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!
🌎 PS there are direct flights from London to Portland and it’s ONLY 9 hours 50 minutes to get halfway across the world!
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