Planning the perfect Oregon road trip itinerary doesn’t have to be stressful or overwhelming!
Oregon has so much to offer including lively cities, great wineries, a gorgeous coastline, amazing waterfalls, and stunning mountains.
I love to road trip Oregon and have explored the state from top to bottom. I have yet to be disappointed by a single place! If you are planning a trip to Oregon, I am here to help!
Highlights of this road trip planner for Oregon include:
- Portland
- Multnomah Falls
- Mount Hood
- Willamette Valley Wineries
- Oregon Caves National Monument
- Samuel H. Boardman State Scenic Corridor
- Cannon Beach
My Oregon example itinerary is written in a clockwise manner around the state, beginning and ending in the Portland area. Feel free to modify it for your interests and do it on your own schedule.
Don’t forget to check out my detailed road trip packing list so you don’t forget any essentials!
Get ready to plan the best Oregon vacation itinerary!
Oregon Road Trip Map
To save you some time, I created this Oregon road trip map. Click the link below and plug the map into your GPS.
Sometimes having a visual of where you are going is very helpful when planning a road trip!
This Oregon road trip map will help you plan your stops and get an idea of where they are located.
Click Here For Oregon Road Trip Map
Bucket-List Oregon Road Trip Itinerary
Start Your Oregon Road Trip By Flying Into Portland
Portland is the largest city in Oregon and also the most accessible to fly into to begin your Oregon road trip.
Both affordable international and domestic flights fly into Portland. I recommend checking out Skyscanner to find the best and most affordable flights. You can easily compare rates.
Alternatively, if you have a shorter amount of time, I recommend flying into Eugene, Oregon.
Eugene is centrally located so you can do either the top or bottom half of the state more easily, depending on your schedule and desires. Flying into Eugene can be more expensive than Portland, however.
After landing in whichever airport you choose, you can pick up your rental vehicle and hit the road!
Stop 1: Portland And The Columbia River Gorge
In case you didn’t know, the motto of the city is “Keep Portland Weird” so you really want to stop in Portland for at least a day to check it out before you begin your Oregon road trip.
I stayed in Portland for 4 days and used it as a base to explore the nearby Columbia River Gorge but you can choose to fly in, see the city, and then head out to nature if you prefer.
There is so much to see and do in Portland!
I recommend visiting the world-famous Japanese Garden which will transport you to another culture. Washington Park is another great stop as well if you love the outdoors.
Where Portland really shines is the food scene. During your time in the city, check out some of the food carts! They have drawn international acclaim and once you take a bite, it is easy to see why!
From sweets and crepes to pho and comfort food, the food carts in Portland will not let you down!
If you have never checked out Voodoo Doughnut, it is a bit touristy but a classic! I promise you it is delicious and worth the wait.
Book Here: City of Portland Tour: Historic and Iconic Sights
Book Here: Portland: All-Inclusive Walking Food Tour
The Columbia River Gorge is a magical stretch of land about 45 minutes away from Portland! To explore it, you can either camp nearby, stay in Portland, or stay in the nearby town of Cascade Locks.
The Columbia River Gorge is filled with beautiful waterfalls and hikes, making it one of the top Oregon travel destinations!
Best Columbia River Gorge Road Trip Stops
Multnomah Falls. Multnomah Falls is an Oregon itinerary classic! You’ve probably seen at least one photo of this popular waterfall!
Multnomah Falls is the most popular stop in the Columbia River Gorge area and it is easily accessible from the road. Walk to the base of the falls or take a short hike and cross over the iconic bridge.
I recommend taking the short hike as the view from the bridge is beautiful!
Latourell Falls. I love Latourell Falls because you can see basalt columns up close and personal.
This is the closest waterfall to Portland and makes a great first stop on your Oregon road trip.
There is a Latourell Falls hike that is 2 miles, but you only have to walk a few feet from the parking lot to see the actual waterfall so don’t let the hiking distance put you off!
Wachella Falls. I highly recommend a visit to this beautiful waterfall!
Wachella Falls is an easy 2.4-mile round-trip hike. It is perfect for families or people who don’t want to hike super far for a great payoff!
Wachella Falls is a great afternoon hike and the shade from the gorge protects you from the sun if it is a hot day. Pack a picnic lunch!
Book Here: From Portland: Columbia Gorge Waterfalls Tour
Recommended Time To Spend
Set aside at least one day to explore Portland if you are looking for a city atmosphere.
Depending on what you want to do in the Columbia River Gorge, I recommend spending 1-2 days exploring the area especially if you want to do a lot of hiking.
If you are on a limited schedule, you can do the Columbia River Gorge area in one day on your out of Portland. Start your day early so you have enough time to see everything.
Best Hotels In Portland:
- The Nines, a Luxury Collection Hotel. Check Rates: Booking.com
- Bluebird Guesthouse. Check Rates: Booking.com
Stop 2: Mount Hood
Mount Hood is the most famous mountain in Oregon and is actually a volcano! This is such a unique stop on a road trip in Oregon.
Mount Hood is located a little over 2 hours away from Portland and you will pass through the Columbia River Gorge on your way there.
One of my favorite views of Mount Hood is from Trillium Lake. This lake is very easily accessible and a great spot to watch the sunset or to shoot astrophotography.
If you want to do more hiking, Lost Lake provides a similar view to Trillium Lake but takes more effort to get to.
Mount Hood is the perfect stop on your eastern Oregon itinerary if you love adventure and the outdoors!
You can drive up Mount Hood itself and there is a lodge at the top. If you are planning the best trip to Oregon during the winter or fall, Mount Hood may have snow and the peak is open for skiing!
In the summer, many of the best hikes in Oregon start from the lodge on top of the mountain.
Book Here: Portland: Mt. Hood Day Tour
Recommended Time To Spend
We recommend spending at least one night exploring the Mount Hood area. Mount Hood is centrally located between the Columbia River Gorge and Bend, your next stop, so if you just have to catch it as you pass by, that is okay too!
At a minimum, you should try and visit Trillium Lake for some wonderful mountain views as it is one of the nicest places to see in Oregon!
Best Hotels Near Mount Hood:
- Located On Mount Hood: Timberline Lodge. Check Rates: Booking.com
- Beautiful, Modern Lodge: Cooper Spur Mountain Resort. Check Rates: Booking.com
Stop 3: Painted Hills And Smith Rock
Did you think you would see the desert during your Oregon road trip? The Oregon Desert takes up most of the state. It just doesn’t get much love when people are looking for places to visit in Oregon.
I recommend getting an early start as the Painted Hills are a bit out of the way and it takes about three hours to reach them from the Mount Hood area.
The Painted Hills are unique and in a very rural area of Oregon, so I highly recommend ensuring your gas tank is completely full before venturing out.
When visiting the Painted Hills in Oregon, I suggest doing the Painted Cove Trail and the Painted Hills Overlook. The Painted Hills are nice just to drive around if you don’t want to do any of the walks.
This is the desert so if you visit Oregon during the summer, bring extra sun protection and lots of water!
Finally, don’t ever step off the approved trail as these locations are very fragile and even one set of footprints will ruin the landscape.
If you need to save time on your Oregon itinerary you can skip the Painted Hills and head straight to Smith Rock.
If you have never heard of Smith Rock State Park, you are in for a real treat! This is the true desert on your eastern Oregon road trip. It is a hiker and rock climber’s paradise!
I recommend visiting either during sunrise or sunset if you want to beat the heat. Smith Rock is one of the best places to see in the state. Make sure it tops your road trip to Oregon!
Smith Rock State Park is located just 40 minutes from the adorable city of Bend, Oregon, and about 1 hour from the Painted Hills so it is easy to do both in one day.
That said, many serious hikers and climbers choose to spend multiple days exploring Smith Rock State Park during their Oregon trips.
If you aren’t a big hiker, simply visiting Smith Rock and walking around will be enough. Believe it or not, “the view” is accessible right from the parking lot so you don’t have to go on a long hike.
I was honestly surprised that the more famous view could be seen right from the parking lot and pleased about it too!
If you are looking for a hike, the Misery Ridge Hike is a popular choice. It is quite steep and strenuous so wear proper hiking gear.
This hike will take you to the top of Smith Rock for memorable views as far as the eye can see.
When you are done exploring the area, I recommend spending the night in Bend, Oregon! You will love the brewpub culture, delicious food, and cute downtown!
Recommended Time To Spend
I recommend at least one full day exploring the Painted Hills and Smith Rock State Park. They can both be completed in a day if you leave early.
If you have more time or want to do more hiking and climbing, then you can stay two days in the area.
Best Hotels Near Bend, Oregon:
- Classic: DoubleTree By Hilton Bend. Check Rates: Booking.com
- Budget: Cascade Lodge. Check Rates: Booking.com
Stop 4: Oregon Waterfalls And Hot Springs Near Eugene
After Bend, you will head through a stunningly rugged mountain pass that is now a lava field as far as the eye can see. This is a great photo opportunity as lava fields aren’t common in the United States!
Once you cross through the lava field, you will pass from the desert into a beautiful lush forest. This is one of my favorite parts of this Oregon itinerary and you are going to love it!
Proxy Falls
As you descend the mountain pass, you will enter the forest that is home to the stunning Proxy Falls! This is my favorite waterfall on this itinerary for Oregon!
This waterfall is breathtaking in person and you really can’t tell how large it is until you get up close!
Proxy Falls Loop Trail is a well-trafficked, 1.6-mile trail. It is well-marked and I consider it easy. It winds through a beautiful forest and down along a mossy lava field before you arrive at Proxy Falls.
I recommend taking the trail to Lower Proxy Falls which will bring you to the base. Be warned: the final hike down to Lower Proxy Falls is quite steep and may not be accessible for everyone.
If you can’t hike all the way to the base, there are a few lovely viewpoints where you can see the entire falls without the steep downhill hike.
Sahalie And Koosah Falls
After Proxy Falls, continue to Sahalie Falls and Koosah Falls. These waterfalls are located along the crystal-blue McKenzie River and are some of the best waterfalls in Oregon!
Both Sahalie and Koosah Falls are very easily accessible from the parking lot and there is virtually no hike at all to see these stunning waterfalls!
Sahalie Falls thunders down over a ledge and Koosah Falls ends in a perfectly blue pool of water.
Don’t skip these waterfalls because you can see them quickly and be on your way. Both of these waterfalls make noteworthy stops on an Oregon road trip!
Make sure to check road closures before heading out to these waterfalls.
Tamolitch Blue Pool
Tamolitch Blue Pool is one of the best places to visit in Oregon if you are looking for something unique during your trip!
This fascinating water feature is located along the McKenzie River Trail! This pool is crystal clear to the point that it appears to only be a few feet deep. In reality, it is closer to 30-40 feet deep!
Tamolitch Blue Pool is marked as one of the best swimming holes in the world, but this is false and you should beware! The water here, although beautiful, is extremely cold, in the 30s, and is not meant for swimming.
The forest service regularly has to save people who have jumped in and been shocked by the cold water.
Plus, swimming in Tamolitch Blue Pool will ruin it because of the oils on your clothes and skin as well as your makeup or sunscreen.
When visiting, I urge you to look with your eyes and not jump in the water for both your sake and the environment.
Terwilliger Hot Springs
Since I am on a “blue” theme, Terwilliger Hot Springs is an interesting addition to your itinerary.
These Oregon hot springs are tucked away in the mountains in the McKenzie River area and look like something out of a storybook.
They are clear, blue pools heated by the lava underneath the volcanic mountain, and you have a view of the forest while you soak. There are also multiple pools with varying temperatures.
Keep in mind that nudity is allowed at Terwilliger Hot Springs and if you decide to make this a stop, you need to be prepared.
You can wear swimsuits as I did, but other bathers may not so you need to make sure to be respectful.
There are even families with kids at Terwilliger Hot Springs, despite it being a nude hot spring.
Visit Eugene For Brew And Foodie Culture
You will spend the night in Eugene, Oregon, which is the hub of central Oregon.
There are so many delicious places to eat in Eugene, and I particularly love the 5th Street Public Market. It is a unique little area with shops and dining.
Eugene is a college town so there may be a college football game during your stay. This is a very busy time for Eugene so be sure to plan ahead as lodging options can fill up quickly.
Recommended Time To Spend
I highly recommend spending at least 1 night in Eugene and giving the entire McKenzie River area 2 full days to explore.
You may want to use Eugene as a “base” to explore the next two stops or continue and stay in the heart of each future stop. Since the next two stops are nearby, Eugene may have affordable lodging options.
Best Hotels Near Eugene:
- Mid-Range: Downtown Inn. Check Rates: Booking.com
- Luxury in Downtown: Graduate Eugene. Check Rates: Booking.com
Stop 5: Wine In The Willamette Valley
If you love wine, you are going to love the Willamette Valley! It is home to over 500 wineries and is second only to Napa Valley in the United States for the production of wine.
Sounds crazy, right? I thought so too until I saw what a Willamette Valley winery looked like!
The Willamette Valley is 150 miles long and you can either stay in a local bed and breakfast in the valley or use Eugene as your base.
I visited King Estate Winery and was majorly impressed! King Estate Winery is like being in Tuscany, Italy! The landscaping, the vineyards, and the huge manor house all come together to transport you to Italy!
If you are into wine, you can spend a good portion of your Oregon road trip sipping wine and eating cheese and crackers.
Book Here: Willamette Valley Wine Tour
Recommended Time To Spend
If you want to experience the Willamette Valley on your Oregon road trip and aren’t hugely into wine, you can spend a morning or afternoon exploring the wineries.
If you are a big wine fan, you could easily spend 1-2 full days in the Willamette Valley wine region because there is so much to see and do!
You may even want to skip this stop altogether if wine isn’t your thing.
Where To Stay In The Willamette Valley:
- Beautiful B&B: LANZAROTTA Bed and Breakfast. Check Rates: Booking.com
Stop 6: Covered Bridges In Cottage Grove
Cottage Grove is a hidden gem along your Oregon trip, and I highly recommend visiting the little town. It is located less than 45 minutes from Eugene. If you want to pop over for a day trip, it is easily accessible.
If you think covered bridges are boring, you are mistaken! They are super fun and a unique piece of history. Plus, Oregon is home to the most covered bridges west of the Mississippi!
Cottage Grove is home to a covered bridge trail. You can choose to either drive or take a bike along the road and visit them all. I recommend driving and getting out at each covered bridge.
There are covered bridges located right in the heart of Cottage Grove and others that you need to see by driving a bit outside of town. You will love all these covered bridges in Oregon!
While in the Cottage Grove area, you can get off the beaten path and visit some lesser-known waterfalls once you are done hunting covered bridges.
Pinard Falls, Spirit Falls, and Moon Falls are all located within 45 minutes of Cottage Grove.
Each waterfall is located down a small dirt road high in the Umpqua Forest and requires a short and steep moderate downhill hike to get to. Find more info about waterfall wandering in Cottage Grove!
Cottage Grove is definetly a great hidden gem for the best Oregon road trips!
Recommended Time To Spend
I suggest spending at least 1 day exploring Cottage Grove during your trip to Oregon!
If hidden waterfalls and covered bridges don’t sound interesting, you can skip Cottage Grove. But if you want to explore the area, you are going to need at least one full day to do it justice!
Where To Stay In Cottage Grove Oregon:
- Mid-Range with a Pool: Best Western Cottage Grove Inn. Check Rates: Booking.com
- Mid-Range: Cottage Grove Inn. Check Rates: Booking.com
Stop 7: Oregon Caves National Monument
Did you know there are caves in Oregon? The Oregon Caves are the most detailed cave system west of the Mississippi and something you shouldn’t miss.
The caves can be accessed from the small town of Cave Junction along highway 199. Once you turn off the road, it is quite a long and winding drive up to the Oregon Caves.
Keep in mind that the caves are cold and damp so dress appropriately. If you don’t have warm clothes, the Ranger Center has free jackets you can wear when exploring the caves.
This is a great stop if you are traveling with kids as they love the caves and there are lots of programs including Junior Ranger programs and Ranger-led walks.
Recommended Time To Spend
I suggest spending between 1-3 hours exploring the Oregon Caves! That should be enough time to visit the caves and enjoy the Visitor Center.
Where To Stay In Grant’s Pass [Closest City To Oregon Caves]:
- Mid-Range: The Lodge At Riverside. Check Rates: Booking.com
- Beautifu Hotel with Pool: Redwood Hyperion Suites. Check Rates: Booking.com
Stop 8: Samuel H. Boardman State Scenic Corridor
The Samuel H. Boardman State Scenic Corridor is my absolute favorite part of this Oregon road trip guide! I love this little slice of the Oregon coast and it is essentially a mini-road trip in itself.
There are over eleven awesome stops here and each one has something unique to offer.
My favorite part is Natural Bridges and Secret Beach. I have been back to each of these places multiple times and each time I am stunned at the beauty and scale of each.
If you want to find the top viewpoints at Natural Bridges, check out my article on the best photography locations in Oregon.
If you want to focus more on the Oregon coastline, I also have a detailed Oregon coast road trip itinerary.
Best Samuel H. Boardman State Scenic Corridor Stops:
- Arch Rock (Mile 344.8)
- Secret Beach (Between Mile Marker 344-345)
- Spruce Island (Mile 345.0)
- Thunder Rock Cove (Mile 345.8)
- Natural Bridges (Mile 346.0)
- North Island (Mile 347.4)
- Thomas Creek Bridge (Mile 347.8)
- Indian Sands (Mile 348.6)
- Whaleshead Overlook (Mile 349.3)
- House Rock (Mile 351.2)
- Cape Ferrelo (Mile 351.9)
- Lone Ranch Picnic Area (Mile 352.6)
Recommended Time To Spend
Some people head through the Samuel H. Boardman State Scenic Corridor in a single day. I personally think that is way too fast but if you are pressed for time, it is still 100% worth the stop.
If you want a more detailed experience, I recommend between 2-3 days here because there are so many hikes and stops.
I have even spent as long as 4-5 days here so you know that it is just a really fantastic stop when taking a trip along the Oregon coast.
Hotels Near Samuel H. Boardman:
- Affordable: Brookings Inn Resort. Check Rates: Booking.com
- Rental Home with Views: Whaleshead Ridge. Check Rates: Booking.com
Stop 9: Bandon And Florence Beaches
After you leave Samuel H. Boardman State Scenic Corridor located on the southern Oregon coast, you are going to visit some wonderful stops on the mid-southern coast.
This is a stunning part of the Oregon road trip itinerary and Bandon is my second favorite stop along the Oregon coast.
Bandon is such an underrated stop and the beach is everything you would hope for in a Pacific Northwest beach.
Bandon Beach is home to towering sea stacks, sea caves, tide pools, and walking trails. It offers so much to see and do!
If you can, make sure to go at low tide so you can walk into the sea caves. Just be sure to not stay out there too long because you don’t want to be stuck in rising water!
Seeing the sunset on the beach in Bandon is a must-do and I highly recommend it!
Where To Stay In Bandon:
- Mid-Range: La Kris Inn. Check Rates: Booking.com
Once you are done in Bandon, head to Florence which marks the middle point of the Oregon Coast. Florence is one of the quaint towns on the Oregon coast and really evokes a vintage flair.
Another unique location? The Oregon Sand Dunes is located just to the south of Florence! The Oregon Sand Dunes are so much fun landscape to explore.
Finally, make sure to stop at Thor’s Well, about 30 minutes north of Florence, either while you are staying in the town or while you proceed along to the northern Oregon coast.
Recommended Time To Spend
I recommend spending one day in Bandon and one day in Florence.
If you don’t have two days, then spend one night in Bandon and drive through Florence with stops at the Oregon Sand Dunes and Thor’s Well.
Where To Stay In Florence:
- On the Beach: Driftwood Shores Resort. Check Rates: Booking.com
Stop 10: Cape Kiwanda And Cannon Beach
Cape Kiwanda and Cannon Beach are a few hours away from each other and offer similar yet unique experiences.
Cape Kiwanda is famous for a huge sea stack that sits out in the water. Here, you can drive straight onto the beach when allowed and then walk along the sand dunes to explore and hike.
When you visit Cape Kiwanda, I suggest taking your shoes off and walking around in bare feet. If you hike in shoes, they will fill with sand and get bogged down making it uncomfortable and hard to walk.
Where To Stay In Cape Kiwanda:
- Mid-Range: Inn At Cape Kiwanda. Check Rates: Booking.com
Cannon Beach is 1.5 hours north of Cape Kiwanda and is the furthest north you will visit on this Oregon road trip.
Like Cape Kiwanda, Cannon Beach is home to a massive sea stack that sits right off the beach. Unlike Cape Kiwanda, the sea stack here is much closer to the beach so you can really feel the presence of the towering rock.
Almost all Oregon road trip itineraries include Cannon Beach because it is so famous!
I highly recommend adding both of these stops to Oregon driving routes as both beaches are so pretty!
Book Here: From Portland: Oregon Coast Day Trip Cannon Beach Area
Recommended Time To Spend
I suggest spending a few hours in Cape Kiwanda and then spending the night at Cannon Beach. If you want to do serious hiking at Cape Kiwanda, then schedule more time here.
If you start early, you should have enough time to hit both Cape Kiwanda and Cannon Beach all in one day.
Cannon Beach is a very popular seaside town so it is a great way to end your Oregon road trip with a walk along the beach and some relaxation before flying home.
Where To Stay At Cannon Beach:
- Great Views: Inn At Haystack Rock. Check Rates: Booking.com
- Affordable: Ocean Front Motel. Check Rates: Booking.com
End Your Oregon Road Trip In Portland
Once you finish exploring Cannon Beach, you have less than a two-hour drive to get back to Portland. This drive is very easy and quite scenic.
I love how you can see the progression as you leave the beachy coast of Oregon and head up through the mountains before coming through a tunnel and arriving back in Portland.
If you didn’t have enough time to explore Portland at the beginning of your Oregon road trip itinerary, now is a great time to have a day or two in the city.
If you are flying out the same day you leave Cannon Beach, the drive from Cannon Beach to Portland is very easy with little traffic so as long as you leave enough time.
Now you know how to plan a trip to Oregon and see all the best towns, slices of coastline, waterfalls, and hidden gems!
I hope you have a great time exploring Oregon by car! Next, check out my tips for traveling to Oregon!
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