Oregon Road Trip Itinerary

Oregon Road Trip

Road Trip Oregon

When it comes to planning out what to do in Oregon, the options are endless! This state really is breathtaking, and I was blown away by its beauty. We had 6 days to drive from Medford, to the coast, up to Portland, and back to the coast again.

We wanted to see as much as possible, and this guide encompasses pretty much everything you need – from stunning waterfall hikes to lavender fields and sandy beaches, you will get your miles worth! Without further ado, here are my top 5 places to include in your Oregon Road Trip itinerary!

Oregon Road Trip Itinerary


Crater Lake was formed from a volcano eruption many years ago. It has absolutely no runoff, and has been filled over the years by snow and rain, so you can bet that water is CRYSTAL! There are a couple of hikes you can do, book a boat tour, or drive around Rim Drive.


Toketee Falls was my favorite waterfall we saw in Oregon, mostly because the water was so blue, and also because the hike down to the falls was kind of difficult, so it felt like I was able to enjoy the journey more! We were told that someone had died at the falls the week previously, so they had placed up a fence and blocked the trail down to the falls. Shane and I naturally jumped over the fence, and carefully climbed down the 20-foot drop led by a rope. WORTH IT, but be very careful!

We last minute decided to go to the Umpqua hot springs because they were so close to Toketee Falls. These hot springs are really cool for pictures but don’t expect anything glamourous. There was one very interesting naked character there with blue dreads and some scary-looking tattoos. We relaxed there for a bit, got some pictures, and headed on our way. Pro-tip – the very first hot spring is the warmest, but the more scenic ones are at the end!


We grabbed some coffee in Portland and headed out to the Columbia River Gorge and Mount Hood to hit these three hot spots! Our original plan was to hike Angels Rest, but it was closed because of the fires. We decided to do a quick loop hike at Latourell Falls first.

Lavender Valley was next on the list, and driving with Mount Hood in the foreground was out of this world! Make sure to buy some honey and lavender bath salts as a gift for your mom, and don’t get stung by any bees. Keep in mind- this place closes at 5 PM, so plan accordingly.

We wanted to make it to Rowena Crest for the sunset and we had some time to kill, so we opted to stop at the random Chinese restaurant in Mount Hood for dinner. It was surprisingly very delicious and they had an awesome happy hour! You can also kill some time at the wineries nearby.

Rowena Crest is located along the Historic Columbia River Highway, a 75-mile long scenic drive. We took the easy way up to the viewpoint by way of our Land Rover, but you can also do this hike!

If you’re looking for a fun place to stay after your long day, this Air Bnb was located right outside of Portland and came equipped with an outdoor shower/bathtub, and my favorite, GOATS! Treats were even provided to us so we could feed them! It was a little over an hour’s drive back from Rowena Crest.


Our original plan was to light a fire on the beach and sleep in the back of our Land Rover that we rented from the app Turo, which is basically like Air Bnb but for cars!

We didn’t really plan ahead, and we forgot the basic necessities like a blanket and pillows. But we still were able to get the full Cannon Beach experience. If you arrive at Haystack Rock a good 1-2 hours before low tide, you can do what’s called “tide pooling” and find lots of little sea critters and maybe a starfish if you’re lucky!

We then paid 5 dollars to enter Ecola State Park and flew the drone around and relaxed with some beautiful views of the beach. We watched the sun go down and grabbed dinner at the most amazing seafood restaurant, Driftwood. This was where we messed up. We were SO FULL after dinner and the beach was SO COLD that we couldn’t bring ourselves to go down to the beach and light a fire. We then got discouraged because we couldn’t find a place to park and sleep, and we didn’t want to drive all the way back to Portland – so we last minute booked a hotel. PLAN AHEAD FRIENDS!

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Oregon Road Trip Itinerary

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