From the enchanting coastline to the pine forest mountains, the lush vineyards of Willamette Valley to the beautiful waterfalls of the Columbia River Gorge; Oregon is a gorgeous state that is best enjoyed outside! On this Ultimate 4 Day Road Trip Itinerary you will have plenty of opportunities to explore all the natural beauty Oregon has to offer.
Follow along below to plan your next road trip vacation!
Day 1 - Portland to Crater Lake
Distance: 300 miles
Drive Time: 5.5 hours
The Route: I-84 East to Hood River, OR-35 South to US-26 East to Bend, US-97 South to Crater Lake National Park
Notable Stopping Points: Columbia River Valley Waterfalls, Hood River, Mt Hood National Forest, P.S. Ogden Scenic Viewpoint Bungee Jumping, Bend, Crater Lake National Park
Columbia River Valley
Be sure to leave Portland early this morning, as it’s going to be a long day full of driving and adventuring! The quickest route from Portland to Crater Lake takes just over 4 hours, but I recommend the 5.5 hour route we took. The first hour of the drive is one of prettiest sections of the route. You will be driving alongside the Columbia River and have multiple opportunities to stop for a quick hike or to view a waterfall.
The most famous waterfall in the area is Multnomah Falls, partly due to its grand height and partly because it’s right off of the road, no hike required. The parking lot and viewing area can get very crowded, so I recommend visiting during the week. We visited at 8:30am on a Thursday and we didn’t have trouble getting a spot, but it was filling up quickly.
The other fall we visited was Bridal Veil, which required a quick hike down to see it. It was much less crowded than Multnomah, but probably only half the height. I would still recommend it as a stopping point though!
There are many many more falls in the area including Horsetail, Wahkeena, Latourell and dozens more. If you have time, I recommend stopping at a few more, but we only saw Multnomah and Bridal Veil because we didn’t want to get to Crater Lake too late.
P.S. Ogden Scenic Viewpoint
This was a completely unplanned stop, but we saw a sign on the highway for a scenic viewpoint and we swerved to get off. It’s basically a rest stop, but next to the this beautiful gorge.
The photo above is the current highway bridge, and the photo below shows the old highway bridge that you can now walk across. There’s also another activity if simply walking across doesn’t give you enough adrenaline. You can bungee jump off of the old bridge, which is exactly what my crazy sister decided to do on a whim.
We found out this is the tallest commercial bungee jump in the country, and bungee jumping is on my sister’s bucket list so she decided to go for it! It was a wild experience that was so fun to watch. How many people can say they bungee jumped at a highway rest stop in the middle of Oregon as a completely last minute decision?
Bend, OR
Bend would be a great stopping point for lunch, or an afternoon snack. We stopped and walked around for a bit, and I thought the town was so cute and it seemed like there was a lot to do. I wish we could have spent more time here.
If you have extra days for your road trip, I’d recommend spending one night in Bend. If you’re just passing through on the way to Crater Lake, Bend is the last large town you’ll see. If there are any specific items you need that you can’t find at a small grocery store or gas station I would buy them here.
Crater Lake National Park
Crater Lake National Park inspired our whole trip to Oregon! After I decided I wanted to visit Crater Lake I realized how isolated it was, so I came up with the mini road trip idea. Crater Lake is a unique place and I really do recommend a visit! Visit the official Crater Lake National Park website for up to date information on entrance fees, lodging, and wintertime road closures.
We stayed in the park and I do think it’s the best option as there’s not much to do or places to stay near the park. We chose to stay in The Cabins at Mazama Village which were around $180/night. The other two options are the Crater Lake Lodge which was much more expensive than the cabins, or to camp at Mazama Campground. You will need to reserve your lodging in the park a few months in advance as they fill up quickly.
The main activities in Crater Lake are looking at the lake (lol!) and hiking. The 33 mile Rim Drive around the lake is a great starting place for both. It has many scenic pullover spots for lake viewing, and several great hiking options. Another way to view the lake is to take a boat tour, but unfortunately they were not operating the boat tours in 2021 due to the pandemic.
If you follow this road trip itinerary you probably wont have time to do a whole lot by the time you arrive at Crater Lake. We decided to just eat dinner at Annie Creek Restaurant, near our cabin at Mazama Village, and to play cards in our room. My hiking recommendations for the park are in the Day 2 section below.
Day 2 - Crater Lake to Eugene
Distance: 125 miles
Drive Time: 2.5 hours
The Route: US-97 North to OR-58 West
Notable Stopping Points: Morning hike in Crater Lake National Park, numerous hikes and scenic lakes in Willamette and Umpqua National Forests, Eugene
More Crater Lake!
The driving time is short today, so enjoy some extra time in Crater Lake before heading to Eugene with a hike or two. We chose to hike to the highest point in the park, Mt Scott at 8,938 feet, and down to the surface of the lake via the Cleetwood Cove Trail.
Both trails are rated strenuous according to the park brochure, but at 4.4 miles and 2.2 miles round trip respectively, both are doable in a single morning. I find this National Park Guide book helpful when trying to select which hikes to do and generally take it to every National Park I visit!
The Cleetwood Cove Trail is the only legal access to the lakes surface. If you would like to jump in the cold water, this is the only place to do it! It is also where you board the boat tours if that is something you chose to do.
Oregon's National Forests
We didn’t make any stops between Crater Lake and Eugene, as we were pretty exhausted from our hikes. However if you’re looking for more places to explore you will pass through one or both of Umpqua National Forest and Willamette National Forest depending on your route. Both areas have countless hiking trails, lakes, and other beautiful areas to explore.
Eugene, OR
Eugene was not originally on my radar as an Oregon destination, but my husband requested that we add it as a stop. He was really excited to visit because he is an avid runner and Eugene seems to revolve around running. Read below for Andrew’s first (hopefully of many) mini features on the blog!
“When we arrived in Eugene Friday night the first thing I needed to do was check out the new Hayward Field. Opened exactly a century ago and named for Oregon’s famed first track & field coach, Bill Hayward, this is the Mecca for track & field fans. It has hosted 8 USA Track and Field Championships this century, the Prefontaine Classic annually since 1975, and countless NCAA Track and Field Championships. The stadium recently underwent a $270 million renovation to handle the increased capacity needed to host the 2022 IAAF Track & Field World Championships. The renovations include a 30,000 seat capacity and underground practice facilities for pole vault other jumping events, and throwing events. The crown jewel of the new Hayward field is the 10-story tower designed to look like the Olympic torch (pictured above). The tower features track and field exhibits and multiple levels for viewing the track.
“Saturday morning I ran on Pre’s trail, a 3.4 mile loop located in Alton Baker Park. The dirt and wood chip trail was created as a memorial to Steve Prefontaine a few months after his passing in 1975. The trail is just a short walk across the Willamette river from the downtown area and was a nice scenic route bordering Oregon football’s Autzen Stadium.” – Andrew
OK it’s Kailyn again! My only note here is that the trails are lovely for a walk as well, if you’re not into running, but beware – the trails will make your shoes absolutely filthy.
In the evening we chose to explore the Whiteaker neighborhood. There are many restaurants hear and in the downtown neighborhood, so pick either area and you’ll be sure to find a great place for dinner.
First we tried a flight of beers at Ninkasi Brewing beforer dinner (pictured above.) We really enjoyed the beautiful outdoor area at Ninkasi, and the large variety of beers they had. It’s a family friendly brewery and they even brew their own kombucha which my younger sister ordered.
For dinner we went to Izakaya Meiji Co which was so delicious, and I would definitely recommend! They serve traditional Japanese food, small plate style and have an extensive cocktail menu. Going with a group of four people was ideal as it allowed us to try many different dishes. My favorites were the tonkatsu (left) and the spicy tuna cocktail.
Day 3 Eugene to the Coast
Distance: 115 miles
Drive Time: 2.5 hours (plus a lot of stopping time)
The Route: OR-126 West to US-101 North
Notable Stopping Points: Sea Lion Caves, Yachats, Heceta Head Lighthouse and Cape Creek Bridge, Thor’s Well, Newport
Here is where my actual itinerary and my suggested itinerary veer apart. I thought it would be a good idea to drive from Eugene, up the coast and over to Portland in one day. It was not a terrible idea, but it definitely was not the best idea. It ended up being too much driving time for one day and we didn’t have enough to time to explore along the coast. This is why this itinerary is set up to drive from Eugene to the coast, stay overnight along the coast, and then hit Portland the next day.
Since we did not have a lot of time, the only places we explored along the coast were the Heceta Head Lighthouse area and the little town of Yachats where we stopped for lunch. We ate at Luna Sea Fish House in Yachats which seemed to be a famous local spot for fresh fish. Our group tried the fish and chips, simply grilled salmon, and fish tacos and we enjoyed everything.
Even though we only made two stops, there are dozens of beaches, state parks, and scenic viewpoints that I wish we had time to stop and visit along US-101. You could easily fill up a whole day even though it’s officially only 2.5 hours of driving time on the schedule.
There are plenty of vacation rentals along the coast but Waldport, Newport, and Depoe Bay are good places to start looking for accommodations for the night.
Day 4 - The Coast to Portland
Distance: 190 miles
Drive Time: 4 hours (plus a lot of stopping time)
The Route: US-101 North to US-26 East for more coastal adventures or US-101 N to OR-18/OR-22 to Willamette Valley for winery tours
Notable Stopping Points: Tillamook Bay, Cannon Beach, Willamette Valley, Portland
More Coastline Viewing or Willamette Valley
Continue up the coast, stopping anywhere that looks interesting to you, until you reach Cannon Beach where you can see the famous Haystack Rock. Here you will turn off the coast and take US 26 back into Portland.
Another option if you’ve seen enough of the coast or are an oenophile is to cut over early on OR 18 or OR 22 to Willamette Valley before heading back to Portland. You will find over 500 wineries located in this fertile valley along with some great farm to table restaurants.
Book your wine tasting in the Willamette Valley through Viator below!
Portland
In our short time in Portland we mainly focused on eating and shopping (hello no state sales tax!) The Pearl District, NW 23rd Ave, and Hawthorn are areas that we explored that are great places to do both of those things. There are also too many breweries to name in these areas. The only one we had time to try was the Deschutes Brewery Portland Public House.
We stayed in Portland for two nights which I think was enough time to see the city. I preferred the other places we stayed in Oregon more, but I’m still glad I got to experience Portland.
Salt & Straw is an ice cream shop with locations all over the West Coast, so it’s not unique to Portland, however if you’re not from the West Coast you should definitely give it a try. It’s kind of pricey as far as ice cream goes but they have really interesting flavors, some of which rotate with the seasons. We visited the 23rd Ave location, but there are several others in the city as well.
Pine State Biscuits, also located on 23rd Ave, is a must try for breakfast or lunch. They have a huge variety of these monster biscuit sandwiches (below) that were sooo decadent and good! They also have yummy breakfast cocktails and other homemade pastries. There will probably be a long line to get in, but wait it out, it is worth it!
Portland is famous for its food trucks, and they have a ton spread all around the city. We decided to check out Hawthorne Asylum on our last night of the trip, which is an outdoor area with a dozen or so food trucks with shared seating all around. It’s a good place to try a variety of cuisines, and everyone can find something they’ll like.
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4 Comments
[…] National Park a few years ago. I think that’s what originally put the idea in my head. Click here to check out what she had to say about […]
I’m so glad to see Andrew contributed to this post! I can’t believe I never spent more time in Oregon when we lived in Seattle, but I really want to go back now. I’m surprised at how big Crater Lake is, and I’d definitely want to hike there (plus do the boat tour)!
I’ve had a couple great trips to Portland but haven’t explore much of Oregon beyond that. I really want to see Crater Lake so I might actually follow this itinerary some day. I can’t believe your sister went bungee jumping on a whim!! I’d forgot that Eugene was such a running destination, but remember it being mention in Kara Goucher’s book. How fun to have Andrew pop in!
You got some good sites there. The deep blue water in Crater Lake is absolutely stunning. As a history buff, I also enjoyed the Oregon Trail sites, the Lewis & Clark sites and the Astoria column.