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The Ultimate Oregon Road Trip Itinerary You Should Steal

Planning the perfect Oregon road trip itinerary doesn’t have to be stressful or overwhelming. No matter where you choose to visit in Oregon, whether it is taking an Oregon Coast road trip or visiting the cities and wineries, you are in for a real treat! We like to call Oregon “The Iceland Of America” as it has so many similarities so if you have been dying to head to Iceland, why not road trip Oregon instead for a fraction of the cost? We have explored Oregon from top to bottom and have yet to be disappointed by a single place. Oregon is a diverse state that offers something for everyone and this ultimate Oregon road trip itinerary hits all the best spots!

Our Oregon road trip itinerary is written in a clockwise manner around the state, beginning and ending in the Portland area, but feel free to modify in any way or go completely against the grain and go counter-clockwise if you are a true rebel!

For this Oregon road trip itinerary, we are not going to specify an amount of time so that you can make the drive as time allows for your schedule. If you have 5-7 days for your Oregon itinerary, then modify this Oregon road trip route to fit that length of time. If you have 2 weeks, consider spending a few days in each location to really take in what Oregon has to offer. No matter what amount of time you choose to explore the state, this Oregon road trip itinerary will not disappoint!

Under each stop, we will recommend the amount of time we suggest spending so you can choose to modify your itinerary accordingly when you road trip Oregon. We will also provide you with a few different shorter Oregon road trip options depending on where you start your flight and if you are driving to Oregon from a nearby state!

The Ultimate Oregon Road Trip Itinerary You Should Steal

The Ultimate Oregon Road Trip Itinerary You Should Steal

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. There are both affordable international and domestic flights that fly into Portland. We recommend checking out Skyscanner to find the best and most affordable flights into Oregon. We use this tool to discover the best flights for our trip because you can easily compare rates. 

If you want to save even more money, fly into a large city in California such as San Francisco and layover there and then fly up to Portland. This is a great way to connect more affordable if you are flying in from abroad. Even for Americans, the flights to Portland are generally quite affordable. We were able to fly to Portland from Tampa, Florida for $375 round trip per person which we think is quite good!

Alternatively, if you have a shorter amount of time to road trip Oregon and you want to cut this itinerary down or see something new, we recommend flying into the city of Eugene, Oregon. Eugene is centrally located so you can do either the “top half” of the state or the “bottom half” of the state more easily, depending on your schedule and desires. Flying into Eugene is a bit more expensive than Portland, which is why we are starting this Oregon road trip itinerary from the big city! Plus, if you have never been to Oregon or Portland, it is a great introduction and place to get excited to see the rest of the state!

Begin Your Oregon Road Trip By Flying Into Portland

Stop 1: Begin Your Oregon Road Trip By Exploring Portland And The Columbia River Gorge

In case you didn’t know, the motto of the city is “Keep Portland Weird” so you really are going to want to stop in Portland for at least a day to check it out before you begin your Oregon road trip. We stayed in Portland for 4 days and used it as a base to explore the nearby Columbia River Gorge [stop 2 on this itinerary] but you can choose to fly in, see the city, and then head out to the nature along the way if you prefer.

There is so much to see and do in Portland. We recommend visiting the world-famous Japanese Garden which will transport you to another culture. It will help you to get inspired before your Oregon road trip begins. Washington Park is another great stop as well if you love the outdoors.

Where Portland really shines if 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 Donut, it is a bit touristy but a classic! We promise you it is delicious and worth the wait. We even have a Voodoo Donut at Universal Orlando now so we can go whenever we have a craving!

Explore the Japanese Garden in Portland during your Oregon Road Trip

The Columbia River Gorge is a magical stretch of land no more than 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 and it is a must on any Oregon road trip. Sadly, the Eagle Creek Fire burned a lot of our favorite Columbia Gorge stops so until the trails are back open, we can only recommend limited options! We will update this post to reflect trail openings when they occur. Please be careful and never start fires in areas that are not allowed!

Best Columbia River Gorge Road Trip Stops

  • Multnomah Falls. Multnomah Falls is an Oregon road trip classic! If you haven’t seen at least one photo of this popular waterfall, you are probably living under a rock. Multnomah Falls is the most popular stop in the Columbia River Gorge area and it is easily accessible from the road. You can walk to the base of Multnomah Falls or you can choose to take a short hike and cross over the bridge that you see in all the photos. We recommend taking the short hike as the view from the bridge is beautiful!
  • Latourell Falls. We love Latourell Falls because you can see basalt columns up close and personal, right in the United States, without ever having to travel to Iceland! Latourell Falls 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 hike distance put you off from visiting!
  • Wachella Falls. We love Wachella Falls and highly recommend putting it on your Oregon road trip itinerary. Wachella Falls is an easy 2.4 mile round trip hike to a beautiful waterfall. It is perfect for families or people like us who don’t want to hike for 12 miles to see beautiful things! Wachella Falls is a great afternoon hike and the shade from the gorge protects you from the sun if it is a hot day!

Recommended Time To Spend: Depending on what you want to do in the Columbia River Gorge and if you are visiting the Columbia River Gorge from Portland or camping nearby, we recommend spending 1-2 days exploring the area especially if you want to do a lot of hiking. Set aside at least one day to explore Portland as well if you are looking for a city atmosphere. If you are on a limited schedule, you can do the entire Columbia River Gorge area in one day on your way east from Portland if you must. If you plan to visit all in one day, we recommend starting that day of your Oregon road trip off early so you have enough time to see everything and still get to your next destination on time.

Where To Stay In Portland:

The Nines, a Luxury Collection Hotel. Check Rates On Booking.com | Hotels.com 

Bluebird Guesthouse. Check Rates On Booking.com | Hotels.com

Begin Your Oregon Road Trip By Exploring Portland And The Columbia River Gorge

Stop 2: Explore Mount Hood For Some Memorable Oregon Road Trip Views

Mount Hood is the most famous mountain in Oregon and is actually a volcano! This is such a unique stop on your Oregon road trip itinerary and a must. 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 our favorite views at Mount Hood is from Trillium Lake. This lake is very easily accessible and a great spot to watch the sunset on Mount Hood or to shoot astrophotography.

If you want to do a bit more hiking, Lost Lake provides a similar view to Trillium Lake but takes a little more to get to. Mount Hood is the perfect stop on your eastern Oregon road trip if you love adventure and the outdoors. You can drive all the way up Mount Hood itself and there is a lodge at top. If you are road tripping Oregon during the winter or fall, Mount Hood may have snow and the peak is open for skiing! In the summer, there are many hikes that start from the lodge on top of the mountain.

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!

Where To Stay Near Mount Hood:

Located ON Mount Hood: Timberline Lodge. Check Rates On Booking.com | Hotels.com

Affordable Option: Best Western Mount Hood. Check Rates On Hotels.com

Explore Mount Hood For Some Memorable Oregon Road Trip Views

Stop 3: Experience The Painted Hills And Smith Rock For A Change Of Climate

Did you think you were going to see desert during your Oregon road trip? The Oregon Desert actually takes up most of the state, it just doesn’t get much love when people are looking for places to visit in Oregon. We 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 very unique and in a very rural area of Oregon so we highly recommend making sure your gas tank is completely full before venturing out.

When visiting the Painted Hills in Oregon, we recommend doing the Painted Cove Trail and the Painted Hills Overlook. This is the desert so if you are taking your Oregon road trip during the summer, you are going to want to bring extra protection and lots of water! The Painted Hills are nice just to drive around if you don’t want to do any of the walks. Finally, don’t ever stop off the approved trail as these locations are very fragile and even one set of footprints will ruin the landscape. If you are looking to save time on your Oregon road trip, consider skipping the Painted Hills and heading straight to Smith Rock.

xperience The Painted Hills And Smith Rock For A Change Of Climate

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 and a hiker and rock climbers paradise! We recommend visiting either during sunrise or sunset if you want to beat the heat. Smith Rock is one of the places to see in Oregon that you shouldn’t miss and it needs to top any 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 all in one day. That being said, many more serious hikers and climbers choose to spend multiple days exploring Smith Rock State Park during their Oregon road trips.

If you are like us and don’t like to hike, simply visiting Smith Rock and walking around will be enough for you. Believe it or not, “the view” is accessible right from the parking lot so if you don’t want to go on a long hike, you don’t have to! We were honestly quite surprised that the more famous view could be seen right from the parking lot and quite pleased about it too! If you are looking for a hike, the Misery Ridge Hike is a popular choice and 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, we recommend spending the night in Bend, Oregon! You will love the brewpub culture and delicious food and cute downtown!

Recommended Time To Spend: We recommend spending at least one full day of your Oregon Road Trip exploring the Painted Hills and Smith Rock State Park. They can both be completed in a day if you leave early. If you don’t have the time or if you want to hike or climb, consider staying the night and spending the day in Smith Rock State Park. Otherwise, one day should be enough time to hit both and spend the night in Bend.

Where To Stay In Bend Oregon:

Classic: DoubleTree By Hilton Bend. Check Rates On Booking.com | Hotels.com

Budget: Cascade Lodge. Check Rates On Booking.com | Hotels.com

xperience The Painted Hills And Smith Rock For A Change Of Climate

Stop 4: Get Up Close With 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 a prevalent thing in the United States and it is unique to see one up close! Once you cross through the lava field on your Oregon road trip, you will pass from the desert into a beautiful lush forest. This is one of our favorite parts of this Oregon road trip itinerary and you are going to love it!

Proxy Falls Is Our Favorite Waterfall On Your Oregon Road Trip

As you descend the mountain pass through the lava field, you will enter the forest that is home to the stunning Proxy Falls! Proxy Falls is our favorite waterfall on this Oregon road trip itinerary and it is one of the best places to visit in Oregon. This waterfall is breathtaking in person and you really can’t tell how large it is until you get up close and in person!

Proxy Falls Loop Trail is a well-trafficked 1.6-mile trail. It is well-marked and we would consider this trail to be “easy.” It winds through a beautiful forest and down along a mossy lava field before you arrive at Proxy Falls. We recommend taking the trail for “Lower Proxy Falls” which will bring you to the base. Please be warned: the final hike down to Lower Proxy Falls is quite steep so it may not be accessible for everyone on your Oregon road trip. 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.

Proxy Falls Is Our Favorite Waterfall On Your Oregon Road Trip

Sahalie And Koosah Falls Are Beautiful And Easily Accessible Oregon Waterfalls

After you finish visiting 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 the state of Oregon has to offer. 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! If you are short on time during your Oregon road trip or if you spent too long at another stop, don’t skip these waterfalls because you can quickly peek and be on your way.

Of course, we do recommend stopping and spending time viewing them if you have it because they are just so breathtaking. Sahalie Falls come thundering down over a ledge and Koosah Falls end in a perfectly blue pool of water. Yes, the water at the bottom of Koosah Falls really does look that blue, it is not just fancy editing which is why both of these waterfalls make noteworthy Oregon road trip stops!

Sahalie And Koosah Falls Are Beautiful And Easily Accessible Oregon Waterfalls

Tamolitch Blue Pool Doesn’t Even Look Real

Tamolitch Blue Pool is one of the best places to visit in Oregon if you are looking for something unique and totally different during your Oregon road trip. Tamolitch Blue Pool is located along the McKenzie River Trail and is quite the beauty! 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 in Tamolitch Blue Pool, although beautiful, is extremely cold, in the 30’s 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 the Tamolitch Blue Pool on your Oregon road trip itinerary, we urge you to look with your eyes and not jump in the water for both your sake and the environment.

Get Ready For Nudity At Terwilliger Hot Springs

Since we are on a “blue” theme, Terwilliger Hot Springs is an interesting addition to your Oregon road trip 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 different pools so you can stay in as warm or cool as you like depending on your preference.

That being said, nudity is allowed at Terwilliger Hot Springs and if you decide to make this a stop on your Oregon road trip, you need to be prepared. Read about our experience here! You can choose to don swimsuits as we 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 the nudity [it’s just a body anyway, right?] so keep that in mind when deciding if this stop is right for you when you road trip Oregon.

Before you go, read our guide on Everything You Need To Know About Nude Hot Springs In Oregon

Everything You Need To Know About Visiting Nude Hot Springs

Visit Eugene, Oregon And Experience Brew And Foodie Culture

You will spend the night in Eugene, Oregon which is the hub for central Oregon. If you want to, you can choose to fly into Eugene instead of Portland to begin your Oregon road trip itinerary if you have already explored north and east Oregon. There are so many delicious places to eat in Eugene and we particularly love the 5th Street Public Market. It is a unique little area with shops and dining. Keep in mind that Eugene is a college town when planning your Oregon road trip 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 with lodging options as it can fill up quickly.

Recommended Time To Spend: We 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 on and stay in the heart of each future stop. Since the next two stops are nearby, Eugene may have affordable lodging options.

Where To Stay In Eugene: 

Centrally Located: Inn At The 5th Eugene. Check Prices On Booking.com | Hotels.com

Affordable\Good Location: Days In Eugene. Check Prices On Booking.com | Hotels.com

Visit Eugene, Oregon And Experience Brew And Foodie Culture during your road trip in Oregon

Stop 5: Relax And Sip Some Wine In The Willamette Valley

If you love wine, you are going to love the Willamette Valley stop on your Oregon road trip itinerary! The Willamette Valley is home to over 500 wineries and is second only to Napa Valley in the United States for production of wine. Sounds pretty crazy, right? We thought so too until we actually 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.

We visited King Estate Winery and were majorly impressed, and we aren’t even huge winos! King Estate Winery is literally like being in Tuscany, Italy! The landscaping, the vineyards, the huge manor house all come together to transport you to Italy when you are really in Oregon! There are 499 other wineries in the Willamette Valley to discover too! If you are into wine, you can spend a good portion of your Oregon road trip sipping wine and eating cheese and crackers.

Recommended Time To Spend: If you just 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 wino, you could easily spend 1-2 full days in the Willamette Valley wine region because there is so much to see and do!

Where To Stay In The Willamette Valley:

LANZAROTTA Bed and Breakfast. Check Rates On Booking.com | Hotels.com 

Relax And Sip Some Wine In The Willamette Valley during your Oregon road trip itinerary

Stop 6: Drive Through Covered Bridges On Your Oregon Road Trip In Cottage Grove

Cottage Grove is a hidden gem along your Oregon road trip itinerary and we highly recommend paying the little town a visit. Cottage Grove is located less than 45 minutes away from Eugene, so if you want to pop over for a day trip, it is easily accessible. Now you may think that covered bridges are boring, like we initially did, but we promise you 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 bridges trail and you can choose to either drive your car as part of your Oregon road trip, or take a bike along the road and visit them all. We 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. Check out our post on 5 Things To Know Before Visiting Covered Bridges In Oregon for a little more information before you go! You can also check out this handy covered bridges map so you can easily find them during your Oregon road trip.

While you are in the Cottage Grove area, you may want to get off the beaten path, even more, to visit some lesser-known waterfalls once you are done hunting covered bridges. The waterfalls are Pinard Falls, Spirit Falls, and Moon Falls and they 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 Here!

Recommended Time To Spend: We suggest spending at least 1-day exploring Cottage Grove during your Oregon road trip itinerary. If hidden waterfalls and covered bridges don’t sound interesting to you and you wish to skip Cottage Grove, that is just fine! 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:

Local And Affordable: The Village Green. Check Rates On Hotels.com

Classic: Best Western Cottage Grove. Check Rates On Booking.com | Hotels.com 

Drive Through Covered Bridges On Your Oregon Road Trip In Cottage Grove

Stop 7: Visit Oregon Caves National Monument & Preserve

Did you know that there are caves in Oregon? The Oregon Caves are the most detailed cave system west of the Mississippi and something that you shouldn’t miss. The Oregon Caves are on our list of top photography locations in Oregon and for a good reason. The Oregon 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. This is a great Oregon road trip stop if you are traveling with kids as the kids love the Caves and there are lots of programs just for them including Junior Ranger programs and Ranger-led walks. If you don’t have warm clothes, the Ranger Center has free jackets that you can wear when exploring the caves. 

Recommended Time To Spend: We suggest spending between 1-3 hours exploring the Oregon Caves during your Oregon road trip itinerary. 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]:

The Lodge At Riverside. Check Rates On Booking.com | Hotels.com

Redwood Hyperion Suites. Check Rates On Booking.com | Hotels.com

Oregon caves are a wonderful oregon road trip stop

Stop 8: Explore Samuel H. Boardman State Scenic Corridor 

The Samuel H. Boardman State Scenic Corridor is our absolute favorite part of this Oregon road trip itinerary. We love this little slice of the Oregon Coast and it is essentially a mini-road trip within this larger road trip. There are over eleven awesome stops in Samuel H. Boardman State Scenic Corridor and each one of them has something unique to offer. Our favorite part of Samuel H. Boardman State Scenic Corridor is Natural Bridges and Secret Beach. We have been back to each of these places multiple times and each time we are stunned at the beauty and scale of each of these stops. 

If you are looking for exactly how to find the best viewpoints at Natural Bridges and how specifically to find Secret Beach make sure to click here and find the name. We include a detailed breakdown on exactly how to find the best spots! 

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 Samuel H. Boardman State Scenic Corridor in a single day. We personally think that this is way too fast BUT if you are pressed for time and you only have one day it is still 100% worth the stop. If you are looking for a more detailed experience we always recommend between 2-3 days here because there are so many hikes and stops along the Corridor. We have even spent as long as 4-5 days here so you know that it is just a really fantastic stop along this Oregon road trip itinerary. 

Hotels Near Samuel H. Boardman:

Brookings Inn Resort. Check Rates On Booking.com | Hotels.com

Gold Beach Manor. Check Rates On Booking.com 

Explore Samuel H. Boardman State Scenic Corridor

Stop 9: Wander The Beaches In Bandon And Florence To Relax During Your Oregon Road Trip

After you leave Samuel H. Boardman State Scenic Corridor located on the southern Oregon coast, you are going to be visiting some wonderful stops on the mid-southern coast. This is a stunning part of the Oregon road trip itinerary and Bandon is our second favorite stop along the Oregon Coast. Bandon is such an underrated stop and the beach is everything you would hope for 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 and you are in for a real treat. 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 wouldn’t want to be stuck in rising water during your Oregon road trip. 

Where To Stay In Bandon:

La Kris Inn. Check Rates On Booking.com | Hotels.com

Wander The Beaches In Bandon And Florence To Relax During Your Oregon Road Trip

Once you are done in Bandon, head to Florence which marks the middle point of the Oregon Coast. Florence is such a quaint town and really evokes a vintage flair which is the best part of the town. Another unique location? The Oregon Sand Dunes located right to the south of Florence! We told you that this Oregon road trip itinerary would cover almost every type of landscape imaginable and the Oregon Sand Dunes are so much fun to explore and see. We recommend spending the night in Florence before you head on to the next part of this Oregon itinerary. 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: We 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. Seeing the sunset on the beach in Bandon is a must-do on your Oregon road trip itinerary and we highly recommend it! Even if you just drive through these areas if you are doing a modified version of this trip, make sure you at least make a quick stop! 

Where To Stay In Florence:

Driftwood Shores Resort. Check Rates On Booking.com | Hotels.com

Thor's Well is a wonderful Oregon coast stop

Stop 10: View Giant Rocks At 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 you can walk along the sand dunes so you can explore and hike. When you visit Cape Kiwanda, we recommend taking your shoes off and walking around in bare feet. If you hike in shoes up the sand dunes, they will fill up with sand and your feet will get bogged down making it uncomfortable and hard to walk. Ask us how we know….because we did it and we don’t want you to make this mistake during your Oregon road trip itinerary. 

Where To Stay In Cape Kiwanda:

Inn At Cape Kiwanda. Check Rates On Booking.com | Hotels.com

View Giant Rocks At Cape Kiwanda And Cannon Beach

Cannon Beach is 1.5 hours north of Cape Kiwanda and is the furthest north you will visit on your 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 at Cannon Beach is much closer to the beach so you can really feel the presence of the towering rock. We highly recommend putting both of these stops on your Oregon road trip itinerary because at Cape Kiwanda the rocks are further out in the water and there are more hikes. At Cannon Beach, the rocks are right near the beach and the coast isn’t rocky but is much flatter and more of a regular beach to walk along. 

Recommended Time To Spend: We suggest spending a few hours in Cape Kiwanda and then spending the night in Cannon Beach. If you are looking to do some serious hiking at Cape Kiwanda, then you are going to want to build in a bit more time to your day. If you start early, you should easily have enough time to hit both Cape Kiwanda and Cannon Beach all in one day on your Oregon road trip itinerary. 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 On Booking.com | Hotels.com

Affordable: Ocean Front Motel. Check Rates On Booking.com | Hotels.com 

View Giant Rocks At Cape Kiwanda And Cannon Beach

End Your Oregon Road Trip Itinerary By Flying Out Of Portland 

Once you are finished exploring Cannon Beach, you have less than a two-hour drive to get back to Portland. This drive is very easy and quite scenic. We 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 to yourself. 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, you should have enough time to make it to the airport in time for your flight. 

The Ultimate Oregon Road Trip itinerary


Packing Tips For Your Trip To Oregon:

Here are some of our favorite items that you should consider packing for your trip to Oregon! These are essential travel items that we use and love and you should make sure to consider for your travels. 

concealed travel pouch may be one of the most important items you bring with you! This unisex RFID blocking concealed travel pouch is lightweight and comes in several colors. It has lots of organization to give you peace of mind. You can keep your most valuable documents safe and secure next to your body.

If you have a pouch already you may not want to or need to invest in a new one. If it does not come with the RFID protection, these RFID sleeves would be handy to prevent identity theft. This configuration comes with enough passport and credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your current pouch or wallet. These are the kind our family uses not only when traveling but at home as well.

If you have a camera on your packing list, you need to add additional memory cards on your list as well. Unless you are packing a computer for your trip, you will not be able to upload photos and clear your existing memory card. Purchasing additional memory cards cost under $20 and take up no space in your luggage. Having a backup can have the potential to save you a lot of heartaches if something goes awry! There is nothing worse than coming across that perfect moment and then finding out you don’t have enough space to capture it on your camera!

Similarly, If you are planning to capture your trip on a smartphone, we beg you to bring some way to back up your memories. The best way to do this is with a portable smartphone flash drive. A flash drive is a small storage device that you can connect up to your smartphone and then safely and easily download the photos onto this device. 

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an external charging battery. This Anker high-speed phone charging battery is the exact one we carry with us on all of my trips. It can be used on a variety of phones, not just an iPhone like we have. And wow is it fast! We like that it holds its charging capabilities for several uses so we do not have to worry about it while out and about. And if we forget to recharge it at night, it will still be good to go the next day.

My mom was never a fan of packing cubes until she tried them out! Now she is soldThese Bagail packing cubes are the exact ones she uses whenever she travels and she travels a lot. She cannot believe how much more organized she is now! And she will never leave without them anymore.

We never leave home on a trip without our Bobble filtration bottle. The 18.5-ounce size is perfect for travel and it will fit nicely in the pocket of a backpack or your purse. Also when filled with water, it is not too heavy to carry. And the Bobble carbon filter ensures fresh clean water whenever and wherever you fill the Bobble. You can find filter replacements here. 

Perhaps you are traveling a long distance and packing space is a premium. Then this set of collapsible silicone foldable water bottles would work well for you. Would not take up much space in your suitcase at all. And you will be receiving a set of two.

You will want to bring a backpack or daypack with you to store snacks, your water bottle, phone, extra clothes, etc.. This foldable water-resistant backpack would be great. It is very affordable and is available in many color options for you to choose from. The fact that it folds down into a zippered pouch will make it easy to pack.

Perhaps you need a more substantial backpack for your international travel. This antitheft backpack has a charging port, is water-resistant and can comfortably carry up to a 15.6″ laptop. It comes in a range of colors to choose from and it is inexpensive as well. 

We all need to protect our eyes from the sun’s harmful UVA/UVB rays. These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of the aviator-style of sunglasses these polarized aviators may interest you. We like polarized sunglasses because they remove the glare off the water and help you to see things more clearly. 

Don’t forget to bring along a universal power adapter if you are traveling abroad. This worldwide power plug is a great example and will charge your phone at the end of your busy days. And this world traveler adapter kit can charge several devices at the same time. This is what you will need when there are several people traveling in your group, or if you bring several electronic devices on your trip that require charging at the same time.

Oregon Road Trip Map

To save you some time, we created this Oregon road trip map just for you. Simply click the link below and plug the map into your GPS. This way you can see how you can modify this itinerary if necessary. Sometimes having a more visual idea of where you are going and what you are about to be doing is very helpful when planning your Oregon road trip! 

Click Here For Oregon Road Trip Map

Oregon road trip map of the itinerary



Oregon is our favorite state and we really hope you enjoy this Oregon road trip itinerary as much as we enjoyed our many visits to this beautiful state! No matter if you are looking for coastal waters or waterfalls or hot springs, Oregon has something for everyone and will surprise you around every turn! 

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27 thoughts on “The Ultimate Oregon Road Trip Itinerary You Should Steal

    1. Follow Me Away Post author

      We stayed in a variety of Aribnbs and also hotels. If you have a place you are looking at [a city for example] we can try and remember where we stayed! We should update this post with all that information! Sorry we haven’t!

      1. melissa

        planning a july trip. DO you know if we could route this to include Crater lake but keep around the same time frame if we were to skip Eugene, Willamette and Cottage Grove?

  1. NancyB

    Cannon beach is gorgeous. Stop at Tillamook for some ice cream. Drift Creek Falls is a nice hike to a suspension bridge. Heceta Head Lighthouse, Hobbit trail to the beach. Sisters, Oregon is a cute little town. Trillion Lake. We did so much more in a week. I planned it all thru Pinterest but due to wildfires, Gorge was closed. Can be reached for more info and pics

      1. Jaswant

        This is an awesome itinerary.
        Planning to go July mid. Is it a good time to do Oregon?
        Can I know how many days trip is this? from the day you guys land to when you flew back?
        What places did you guys spend the nights? We will plan the similar way.


        1. Follow Me Away Post author

          You can do it as long or short as you want. We flew in and out of Portland and took two weeks to do it. Another time we flew into Eugene and did the bottom half of this itinerary and just looped back around in 2 weeks too but we like to spend a long time at each destination. You can do it shorter if you don’t want to spend multiple days seeing each thing!

    1. D C

      Planning a week in June/July, want to see as much as possible, probably skip the eastern Oregon things, can you share itinerary you did? Where should we make sure and see?

  2. Kim McNelis

    Great reviews and tips! So many of these places are on my list!

    I’m heading to Oregon/CA for 2 weeks this summer with my husband and son and am planning the following… Columbia River Gorge 2 nights, Mt Hood 1 night, Bend 2 nights, Crater Lake 2 nights, Redwoods/Klamath 4 nights, Yachats 2 nights. Then we have a final day to head back to Portland for the flight out… so, question for all… would it be better to continue up the coast from Yachats toward Seaside and spend the last night in the state on the beach or head inland and spend our final day touring wineries in the valley?

    1. Lizzie

      Definitely go inland and explore the Willamette Valley! It’s beautiful during the summer and McMinnville has beautiful wineries and tasting rooms. Go to Durant Farms, the view is stunning!!!

  3. BreAnne

    This was the perfect itinerary for my trip to oregon – barely did any planning other than reading up on here and a little more for each place! We did a 6 day trip, cutting out a few things but loved every minute of this trip! Thanks for sharing!!

    1. Follow Me Away Post author

      That is SO AWESOME to hear! And exactly why we designed it this way! Cut out what you want or don’t have time for and do the rest!

  4. Crimson Presley

    You COMPLETELY missed Eastern Oregon!!! And, in my opinion, you missed some of the best gems of the state! i.e. The Steens Mountains! Owyhee Canyon Country! Joseph, Oregon and the Imnaha’s. To bad! More for the rest of us! 🙂

  5. Lizzie

    You should also come and visit McMinnville, Oregon if you’re into wine tastings they have some beautiful vineyards and amazing views if you know where to look! (I don’t live there I just think it’s beautiful.)

  6. Renee McAneny

    We are heading to Eugene in July and will have 5 days do day trips. Eugene will be our hub each night. What do you suggest as must see locations? Thanks. We have seen Florence and Cottage Crove on a prievous trip. I love wine!

    1. Follow Me Away Post author

      Oh gosh so many! Def Proxy Falls, Terwilliger Hot springs, Koosah and Salahie. If you can, make it up to Salem and silver falls state park. You can also go to Smith Rock its far but amazing!

  7. Mary

    Man, if you ever edit or add to this Ashland has to be on that list. Best small town in Oregon, the food, the hikes, the Shakespeare festival!


    Planning a week in December, want to see the beautiful scenes, probably skip the west part of Oregon . What should be the best place to stay there ?

    1. Follow Me Away Post author

      Hello! We recommend hotels for each and every stop on this list! Please let us know if there is a specific area you don’t see! If it isn’t on this list it is probably something we aren’t super familiar with! Thanks1

  9. Patti

    Great information! Planning an anniversary trip in September and want to see the Coast, Columbia River Gorge, and Willamette Valley and whatever else we can fit in to our schedule. Arriving early to Portland on a Thursday morning. Do you suggest we head to the coast right away and head south to avoid crowds there and work our way back to Portland from Bandon to fly home on Tuesday evening? Not sure how to plan our itinerary to dodge weekend traveler crowds. Of course, I am sure we will need to plan another trip to see more of this beautiful state.

  10. Jenny

    Can anyone help? We are visiting Portland for only 3 full days. Any ideas for a condensed road trip? We are flying in on a Thursday afternoon. We have Fri-Sun for full travel days and then need to be in Portland to fly out very early in the AM on Monday. This is taking place next week so October. We have already been to Astoria, Cannon Beach and the surrounding areas a few years ago. So we don’t need to hit up those areas. Oregon is so beautiful that we want to go back. And I’m the type of person that usually wants something new and don’t visit a place twice. Love this state!

    1. Follow Me Away Post author

      I recommend the Columbia River Groge and Mount Hood. OR Head down to Salem and the amazing waterfalls in that area like Silver Falls State Park! Have fun!

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