The Perfect Itinerary for an Oregon Road Trip

The Perfect Itinerary for an Oregon Road Trip

When you start to think about your next American road trip destination, Oregon likely isn’t the first state to come to mind.

In fact, Oregon only comes in at the 28th spot in the ranking of US states’ tourism and visitors.

Don’t let this middle-of-the-road ranking fool you – Oregon is a hidden gem for road-trippers filled with nature, culture, and inspiration that easily rivals its neighbor California (who, by the way, is the #1 state for travel).

It may not be the largest or most popular state, but it’s home to some outstanding road trip adventures. From jaw-dropping scenic highways to one of the most unique and interesting cities in the country — Portland — there’s a diverse array of experiences awaiting every road-tripper who takes the plunge.

Today’s HearHere guide is all about planning a road trip through Oregon. We’re covering things from start to finish to help you plan your perfect itinerary, including tips for when to travel, where to start, which vehicle to use, must-see points of interest, and how best to line them all up.

We’re writing for experts and amateurs alike. If you want to get the most out of your next road trip and you’re considering Oregon as the place to do it, read on!

Why Travel Oregon: Is an Oregon Road Trip Worth It?

Some states are so well known, most travelers go into their planning phase with an idea of the major places they want to see. 

Unless you’re especially familiar with Oregon, native to the West Coast, or have heard anecdotes from other travelers, you might only know of Portland and Crater Lake. 

With such a small window into what Oregon can offer, it’s no wonder so many adventurers skip the state for a more popular road trip option such as California, Utah, Arizona, or Colorado.

After reading today’s guide, we’d wager Oregon will top your list of US road trips you need to take. Oregon has plenty of renowned sites — though newer travelers may be less familiar — but the hidden gems and unexpected stops truly make the state shine.

In other words, Oregon is all about being inspiring. 

Tips for Planning Your Oregon Road Trip Route

With spontaneous stops and detours being so common on Oregon road trips, it can be a little tricky to plan your trip.

The key here is balance: Balance some overall structure with plenty of flexibility and free time between long drives.

Oregon has plenty of sights to see, but it’s the vastness of each stop that sets them apart. You’re rarely going to want to spend less than two days at any given stop in our suggested itinerary below.

Let’s talk more about some guidelines as you figure out itinerary specifics based on your wants and needs.

What’s the Ideal Length for an Oregon Road Trip?

As you start planning your road trip, the essential early question is, “What amount of time is ideal for this area?”

When visiting Oregon, longer is definitely better because of the density of attractions we discussed earlier. Any worries of boredom will be alleviated once you realize how much Oregon has to offer – and if worries remain, they will be shattered once you get on the ground and start to discover new and interesting detours at every turn.

With that said, we recommend traveling for at least two weeks if you intend to get a full experience of Oregon as a state.

You can absolutely achieve an enjoyable experience in less time, but you’re going to have to narrow your focus to do so – otherwise, your trip is bound to feel rushed. 

If you only have a few days but are determined to see a state in its entirety, you may be better off looking to another state and coming back to Oregon when you have more time.

Where To Start and Finish Your Oregon Road Trip

Oregon is most easily traveled in a loop if you intend to see the whole state. The exact details of what should be in the loop vary depending on who you ask, as does the best point of origin for your road trip.

Portland is the most common place to start a road trip in Oregon. It’s the perfect location for anyone coming from beyond driving distance (i.e., not from a neighboring state), thanks to the Portland International Airport (PDX).

The airport is in an extremely convenient location within the city, and it also has abundant flights going in and out (often at affordable rates). Plus, it’s one of the highest-rated airports in the country in terms of efficiency and cleanliness.

Some travelers prefer to drive into Oregon, and it’s easy to see why. Oregon sits conveniently between California and Washington, which means an extended road trip (maybe over a few months) is perfectly suited to a stop here between the Redwoods and Seattle.

Those who drive through Oregon can begin their trip in Portland if they’re coming from the North. If approaching from the Southeast, Crater Lake is a natural starting point, while Oregon’s coastal highways set a trip coming from the Southwest off to a beautiful start.

Is There an Ideal Vehicle for an Oregon Road Trip?

The right vehicle can make or break any road trip. It's hard to go wrong when it comes to an Oregon trip. Still, certain factors may be more ideally suited to your preferences.

For one, there are plenty of opportunities to take advantage of an off-road capable vehicle. You can start your search with a crossover since these cars are the most likely to have AWD or 4WD.

Sleeper vans and campers are also popular options for Northwest road trips, as there are many places where you can sleep in your portable habitat instead of having to pay to book a hotel or Airbnb.

This can be huge in terms of helping your trip budget, although such rentals typically cost more than cars – it doesn’t always balance out if you go with a luxury camper.

Although your time on the road will be lower here than in some bigger road-tripping states like California, Texas, or Arizona, a vehicle with great fuel economy is always a good choice. With Oregon being an exceptionally environmentally conscious state, that’s a great way to fit in from the get-go.

What’s the Ideal Time of Year for an Oregon Road Trip?

Oregon is a state with fairly extreme opposites in winter and summer weather, so this decision is significant in terms of your Oregon experience.

July through August are the peak months to visit Oregon, but that doesn’t necessarily mean they’re the best. Greater popularity also equals more crowds. Reservations will be more difficult to secure, traffic may be worse at various legs of your journey, and lines at popular sites will slow down your trip.

In terms of ideal weather, May through October includes the driest and most moderate seasons. Of course, the weather gets cooler the farther we get from summer.

However, an Oregon road trip in the winter has a special charm and plenty of unique upsides. While conditions may be harsh and preparation for safety’s sake is a must, the benefits of winter sporting opportunities are huge. 

Oregon draws skiers and snowboarders from around the world every year, so if you’re a snow sports enthusiast, consider the challenge of a winter road trip!

Whatever time of year you opt for, be sure to diligently monitor any active or potential forest fires, as they can massively alter your plans. Still, with so many unique benefits in each season, there’s never a bad time to explore everything Oregon has to offer.

Oregon Road Trip Itinerary: Places To Go

Now, it’s time for the fun part! Choosing your major points of interest is the bare minimum when planning an Oregon road trip, but there are plenty of hidden treasures to explore. 

We encourage some spontaneity in this state if you’re feeling adventurous. If you’re worried about missing points of interest, add HearHere to your travel team to hear stories about the history of the areas you pass through and for recommendations about local hidden gems!

Starting Point: Portland

This may not be the origin point for everyone’s Oregon road trip, but we’re starting our guide here because it’s so common.

Portland is one of the most unique and inspiring cities in the US, and it doesn’t take long to see why. Immediately upon arriving, you’ll find art, architecture, and culture everywhere you look.

The natural scenery is certainly one of Oregon’s strong suits, but there’s lots to do in this fast-growing urban area.

Where To Stay in Portland?

As far as lodging, there are tons of quirky options within the city, but traditional hotels are also available for creatures of habit (or holders of rewards points). 

Choosing accommodations as close to the heart of downtown as possible makes getting around the city easy as pie. That said, Portland also has some of the best infrastructures in the nation for walking, biking, and public transportation.

Renting a car is the way to go for the rest of this trip, but you won’t need a vehicle while in Portland. It’s a great chance to save some money by being well informed and experience the city like a local.

We recommend spending at least a few days here, although you can spread them out between the beginning and end of your trip if you plan to do a loop around the state starting and ending here.

Part of Portland’s charm is the abundance of great food and drink — Voodoo Donuts, anyone? While you might be able to explore a dozen or so art exhibits around the city in a day, you can only (reasonably) eat and enjoy so many meals and drinks. More days = more meals in this gastronomical wonderland.

Small, local restaurants are everywhere, so there’s no need to resort to large chain restaurants during your visit, unless you are truly craving some Cheesecake Factory brown bread (we’ve all been there). The city also specializes in craft beer, coffee, tea, ciders, and wine from all over the state of Oregon.

Things To Do in Portland

Aside from eating and drinking, there’s an abundance of activites to discover in the gorgeous, funky city of Portland. 

The best part is, you won’t be stuck with the feeling that it’s a “tourist” city. Portland offers a deeply authentic experience reflecting the ways of local life for all who travel there.

This is a perfect place to be open-minded, spontaneous, and curious. Don’t be afraid to check out any hole-in-the-wall business you find. From glow-in-the-dark indoor mini-golf  courses in basements (here’s looking at you, Glowing Greens) to arcades with bars (see also: Ground Kontrol Arcade and Bar), there are interesting options galore. 

Some attractions are too big to miss. Powell’s Bookstore, for example, is a must-see. It’s the largest used and new bookstore in the world, taking up an entire city block.

Another record goes to Portland’s Saturday Market, the largest arts-and-crafts fair in the U.S. Check this one out if your time in Portland crosses over with the weekend.

No Portland trip is complete without seeing some art exhibits. The Portland Art Museum is a more traditional option, while The Freakybuttrue Peculiarium Museum is a bit more off the beaten path but captures the spirit of Portland perfectly.

If you’re into thrifting and vintage fashion, Portland is renowned for its thrift shops and boutiques. Just be careful not to buy more than you can comfortably pack with the rest of your cargo for the remainder of the trip!

Those seeking a bit of outdoors while in the city are in luck, too. The 5000+ acre Forest Park is full of activities such as hikes and trails, while more relaxing times await at the Portland Japanese Garden, Chinese Garden, and International Rose Test Garden (the oldest of its kind in the country).

Next Up: Columbia River Gorge

The Columbia River Gorge is another must-see area in the north of Oregon, running for around 80 miles laterally and accessible less than an hour from Portland. Here you’ll find the Deschutes river flanked by a gorgeous landscape that can scale thousands of feet high.

The gorge is a National Scenic Area, which means it’s well preserved and ready to be explored appropriately. Just the drive alone is worth the trip, but there’s much more to do along the way.

Driving Through the Columbia River Gorge

Hop off the interstate and take the Historic Columbia River Highway to get the best views, leading to the real attraction: the waterfalls. The Columbia River Gorge boasts the densest concentration of waterfalls in the country at a massive count of 90 waterfalls.

If you want to spend days seeing each and every waterfall the gorge has to offer, we commend you. For people with a little less time to spare, here are the must-see waterfalls to stop at on your way (some of which involve fun one- to two-mile hikes):

  • Multnomah Falls
  • Horsetail Falls
  • Wahkeena Falls
  • Latourell Falls
  • Bridal Veil Falls
  • Oneonta Falls

The Portland Women’s Forum vista point is a popular place to watch the sunrise if you make it early enough. Crown point is the perfect place for a sunset view, and Angel’s Crest is another hike worth taking in the area.

After or between seeing the falls, we recommend checking out some of the wonderful wineries in the area. If being flexible is your thing, you could stop by individually on your own, but guided tours offer an extra incentive for the curious lifelong learner.

Where To Stay and Extra Activities Around Columbia River Gorge

Hood River is a nearby town ideal for lodging before your next major attraction. (Spoiler Alert: It’s Mt. Hood.) 

Alternatively, you could use one of the many campgrounds around the gorge. 

Once you’ve secured lodging, linger and enjoy the many activities around the area if you have the time.

Water sports are a favorite here. Check out Naked Falls for a nice swimming hole, but the real adrenaline kicks in with Kiteboarding and Windsurfing. You can find rentals and lessons from several sources along the river.

On to Mount Hood

Depending on where you stay around the Columbia River Gorge, your next major stop (Mount Hood) should be about an hour away. 

The short drives might encourage you to move on quickly between each stop, but don’t forget to do some exploring and take your time if you can. It’s worth it!

Once you arrive, you’ll be greeted by a breathtaking sight: a potentially active stratovolcano. The Mt. Hood National Forest surrounds the mount for over one million acres.

Winter sports are the primary draw to Mount Hood. If you’re an enthusiast or willing to learn, stay at one of the three highly rated ski lodges around the mountain: Mt Hood Meadows, Mt Hood Skibowl, or Timberline Lodge & Ski Area.

You can also find standard lodging options in the surrounding area, including unique and charming AirBnBs and campsites. If you’re on a tighter budget or don’t intend to ski or snowboard, this may be preferable to the lodges. Still, anyone can enjoy a good aprés ski, whether or not you’ve hit the slopes.

You can also enjoy one of the many day hikes in the National Forest. The Mirror Lake loop is a favorite, as is the Tamanawas Falls Trail. Water sports are an option, too, if you want to try kayaking on Trillium Lake.

Numerous hot springs can also be found nearby for the curious adventurer. Even the most well-known, such as Bagby Hot Springs and the Austin Hot Springs, are a bit difficult to find and access, creating a fun challenge for those up to the task.

Explore the Desert Region of Oregon

When you think of Oregon, the first images to come to mind are likely forested coastal cliffs, lakes, miles of coniferous trees under blankets of northwestern rain, and maybe the state’s eccentric and famed capital city. 

Would it surprise you that a large portion of your Oregon road trip will pass through the desert?

The Oregon high desert region is an incredible and surprising leg of the ultimate Oregon road trip flanking Nevada and Idaho on the eastern border of Oregon. Here you’ll find hills, mountains, cliffs, dusty flats, and (most interestingly) volcanoes.

Thankfully, the driving on this leg of your journey is still extremely manageable. From Mt. Hood to Bend, Oregon (the town you’re most likely to stay at) is a mere 2.5-hour drive.

Before you get to Bend, you’ll want to line up Smith Rock State Park and the Painted Hills along your route.

Smith Rock State Park features plenty of views for the passerby. Those interesting in rock climbing are in for a real treat, with thousands of climbs throughout the park.

The Painted Hills are another spectacle for the eye, as is typical of the west coast landscapes we follow on our road trips. Not unlike the Painted Desert found further south in and around Arizona, the Painted Hills have a distinct visual quality: bands of color due to layered tiers of different sediment.

Staying in Bend Oregon

Brasada Ranch is the highest-quality place to stay (though not the cheapest). Luxurious lodgings are accompanied by infrastructure for nearly any kind of outdoor adventure activity you could want to get up to in the area, even including horseback riding.

Standard lodging is also available all around Bend, as are numerous camping options. The level of comfort you want is really up to your budget, but there’s something for everyone in this natural wonderland.

Downtown Bend is a charming area, but the wilderness around you is the real reason to visit. Check out views of the 3 Sisters volcano peaks from one of multiple viewpoints, including Summit Park and Dutchman Flat Sno Park.

Wherever you choose to lodge, you can find hiking, biking, horseback riding, water sports, and snow sports in the winter, as well as rock climbing, trail running, and more.

As with much of Oregon, it’s the active, outdoorsy person’s dream. If you need some R&R in-between adventures, spend a laid-back day at the Unofficial Logging Co. ax-throwing bar before swinging by the Tower Theater for some evening entertainment.

Main Attraction: Crater Lake National Park

A 2-hour drive from Bend brings you to the most popular attraction in Oregon and one of the most spectacular sights in this already impressive, eye-candy-laden state: Crater Lake.

Formed by ancient volcanoes, Crater Lake is the deepest lake in the United States, with an average depth of almost 2000 feet. For a quick comparison, the Empire State Building is 1250 feet tall.

The pristine condition of the deep blue water is also legendary, drawing droves of tourists here every year. Remember that activities here are more likely to sell out than some of the other parks on this itinerary — but the effort will be well worth it.

When To Visit Crater Lake: Seasons and Reservations

Planning ahead is key for this leg of the journey, so book any reservations a few months in advance if possible. There are numerous activities you might want to reserve.

Lodging, for one, could be reserved at the Crater Lake Lodge (with an excellent view), or one of the campgrounds around the park. Alternatively, you could stay in a nearby town like Chemult, Chiloquin, or Fort Klamath.

You may also want to reserve boat or trolley tours, although whether or not these tours will run in 2022 is still unknown, according to the national park’s website.

In the summer season, the park recommends arriving before 9 AM or after 4 PM to avoid crowds and long lines.

Note also that seasons greatly affect Crater Lake. During the winter months (November through April), multiple entrances of the park are closed, and certain services and accommodations are limited or unavailable. This is mostly due to extremely heavy snow in the area.

However, with winter closures also comes winter activities. By accessing Crater Lake through one of the two plowed drives, you can enjoy the gorgeous view under a layer of white snow, then get involved in some high-octane winter adventures: skiing, sledding, snowmobiling, nordic skiing, and more!

What To Do at Crater Lake

It’s no surprise that the sights of Crater Lake are the main attraction. You’re not going to want to rush away as you gaze upon the landscape before you.

There are 30 overlooks around the lake (some of which will be closed during the winter) that offer unique area views. Some of our favorites include the Phantom Ship Overlook, Cloudcap Overlook, and Pinnacles Overlook. Don’t miss the Sinnott Memorial Outlook by the visitor center too.

To see the overlooks, driving the 33-mile historic Rim Drive, which circles Crater Lake entirely, is the best option.

Crater Lake national park can also be more than a sight-seeing stop for those who want more. Swimming is available in designated areas, but the water is frigid. As mentioned previously, reserving boat or trolley tours has historically been available, although the service is in question for 2022.

You can even fish here with the right permissions! Talk to the park office to learn more.

While we’ve been pushing a longer stay at most stops through Oregon, and this is easily one of the most brilliant places to see, it’s not necessarily the most densely packed in terms of activities. 

One full or mostly full day at Crater Lake should be plenty, but taking more time here to camp, hike, and explore is never a bad idea.

Head To the Oregon Coast

The final leg of our journey is also the longest by far — with dozens of possible stops — but none that particularly stand out from the others in the same way as Crater Lake or Portland. Still, just because these stops aren’t hashtag iconic like some of the others on your itinerary doesn’t make them any less inspiring, transformative, or entertaining.

Heading to the Oregon Coast is the most flexible leg of an Oregon road trip journey and where your personal preference comes into play most.

Before we even get to the coast, you’ve got a three-hour drive ahead of you. However, 40 minutes in, we recommend taking a very small detour to see Tokeetee Falls. 

An 0.8-mile hike from the road gets you to this gorgeous view. If you haven’t had your fill of waterfalls even after seeing the Columbia River Gorge, here’s another to wow you once again.

Returning to the main route and finally reaching the coast, you’re in for an experience reminiscent of California’s coastal highways, with a unique Oregon spin.

Where To Stop on the Oregon Coast

There are so many options for places to stop on the Oregon coast, all of which are so excellent, it’s almost impossible to recommend one over the other. However, there are a few we feel are must-sees.

Before returning to Portland or driving wherever else the road takes you at the end of your journey, Ecola State Park on the northern edge of the coast is a beautiful site you won’t want to miss. 

Whether you hike or drive to the beach, you can experience the lush rainforest and a peaceful atmosphere next to the sound of the waves. It’s the perfect place to soak in the end of your journey.

The Three Capes Scenic route is a perfect way to see a variety of views, bringing you to three unique capes: Cape Meares, Cape Lookout, and Cape Kiwanda. A lighthouse, beach access, tidepools, the tallest of three Haystack Rocks in Oregon, and impressive cliffs await.

Lastly, don’t miss the Oregon Dunes National Recreation Area. Forty miles of coastal dunes make this the largest area of its kind on the continent. Use the Jessie M. Honeyman Memorial State Park for the easiest access.

Final Remarks

After venturing the Oregon coast, you can drive back to Portland to return your rental and fly home, or perhaps continue your drive north to see Seattle, Washington and beyond.

Wherever the road takes you, stay inspired with our HearHere audio companion app. 

With HearHere at your side, location-based storytelling from some of your favorite voices comes conveniently to your device while you're on the road or between stops.

Each story informs and entertains, covering the culture and history of the land you travel through, and noting potential points of interest and hidden gems along the way.

Stay curious, and keep coming back to the HearHere blog for all your travel needs!

Sources:

The Most Popular US States for Tourism - Travel | Business Insider

Climate Protection | Oregon Environmental Council

Bookselling Spotlight: Powell's Books | Publisher’s Weekly

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