The Perfect 4-Day Oregon Roadtrip

Oregon is home to many waterfalls, lush forests, and a beautiful coast — perfect for a nature retreat. For any Twilight fans, it’s also well-known for its filming locations.

I visited Oregon in April of 2024. One of my friends from pharmacy school was completing her residency in Medford, so I flew into that city, and we road-tripped up north.

Read on to hear our itinerary for a perfect 4-day road trip in the beautiful state of Oregon.

Day 1

After arriving in Medford late last night, and getting a good night’s sleep, we started the 3-4 hour drive up north to Silver Falls State Park. Here we did the Trail of Ten Falls hike, and loved it! It’s a great hike for all ages — I saw older couples and younger kids alike on the trail. Since we were short on time, we opted for a shorter version of the hike, technically called the Winter Falls Loop which took us to 7 waterfalls (3 of them you could walk behind) and took us 2.5 hours (~5 miles) to complete. The Trail of Ten Falls takes you to all 10 waterfalls and is 7.2 miles long, taking an average of 3.5 hours to complete.

We stayed overnight at the cutest airbnb in Silverton. It’s a Christmas tree farm and lavender farm all in one, with beautiful views of the sunset. There are even pet goats you can pet! (Although we didn’t see them). After watching the first Twilight movie (hey, we had to get in the spirit) with some local wine we grabbed from the nearby store, we called it a night.

Day 2

This morning we checked out the tulip festival at Wooden Shoe Tulip Farm, which is one of the biggest reasons I came out to Oregon during this time. Last year, the peak bloom for the tulips was around April 12th, so I figured it would bloom around the same this year, and I was pretty accurate. Make sure you purchase tickets at least a few weeks in advance as they will sell out! The tulip fields were so beautiful, and you can see Mt. Hood in the background as well. There are so many events going on, such as fair games, vendor stands, and, of course, tulip bouquets to purchase. I wanted to buy some tulips for my friend I visited, but I was worried they wouldn’t last during the road trip… turns out that if you wrap up the stems with a wet paper towel/paper bag, it’ll last!

The next stop on the road trip is Cannon Beach. In typical Oregon fashion, the weather was a little gloomy and chilly when we arrived, but that didn’t stop us from seeing the iconic Haystack Rock and walking along the beach. There are so many birds that lounge on Haystack Rock — if you’re an avid birdwatcher, you can bring binoculars to watch. Then, after checking into our airbnb, we went back out to catch the sunset. Originally, the plan was to go to Cape Meares, but we weren’t going to make it in time. So, we found a sign on the side of the road that said “entrance to beach” and decided to adventure that way. On Google Maps, the beach is called Short Beach. It was so peaceful and beautiful — besides us, there was only another group of two there.

Day 3

Time to do some hikes in Ecola State Park! After grabbing some nearby breakfast, we started the Indian Beach Trail, which had beautiful views of the coast and even takes you to some film locations (Twilight, Point Break, The Goonies). About a mile into the trail, it looked like there was a landslide or some geologic disruption that made it seem unpassable, so we backtracked and began a different trail instead. We hiked the Clatsop Loop Trail which took about 1.5 hours (~3.15 miles). You can see the Tillamook Rock Lighthouse from here.

After feeling accomplished with our time in Cannon Beach, we began the 2-hour drive to the Portland area. We stopped by Sugarpine Drive-In, a famous ice cream place, and enjoyed our ice cream cones by the Sandy River (just walk towards the trail near the drive-in to get here).

Then, we checked out the popular Multnomah Falls. Standing at 620 feet, this waterfall attracted so many different people. As my friend said, “it felt like Disney.” Although it does feel very touristy, I think it’s still a must-stop for first-timers in Portland. You can hike to the top of the falls, and it takes about 1 hour (~2 miles roundtrip), but honestly the views weren’t really that worth it at the top.

For dinner, we met up with my friend Emma whom I met when I solo traveled Lisbon. She happened to move to Portland a couple of months ago, so we met at Shalom Y’all for some delicious dinner and drinks.

pro tip: If you’re parking on the street in Portland, try to park on the closest side of the railroad so you don’t have to wait for the train to pass by… it can take a while!

Day 4

My flight was around 3 PM, so I had the morning to explore downtown Portland. I met up with Emma again and we wandered around Powell’s Books, which is the world’s largest independent bookstore. It was easy to get lost in the place, and I loved reading all the different recommendations and adding them to my Goodreads for later.

Then, we grabbed donuts at The Voodoo Doughnut, which is a Portland classic. Try one of their crazy doughnut creations and stop by the photobooth for some fun!

Emma and her roommate dropped me off at the airport, which was so nice of them. Overall, I really enjoyed my time in Oregon and felt that I saw a nice mix of everything (waterfalls, tulips, beaches, and the city). I think it’s completely do-able for a long weekend if you don’t have much time off from work.