Oregon Road Trip Itinerary: One Week (or More!) in the Pacific Northwest’s Paradise

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Oregon kinda has it all—snow-capped mountains, craggy high deserts, and a wildly stunning coastline—so perhaps it’s no surprise that it’s one of the best states to have an epic road trip. But with SO MUCH cool stuff to see, it can feel like a daunting task to come up with the perfect Oregon road trip itinerary. So if you’re looking for help planning your Oregon road trip, you’ve come to the right spot!

Keep reading the post below for a one week road trip itinerary of the very best sites that Oregon has to offer, plus all kinds of insider tips to help you make your trip as epic as possible (including ideas for other things to see if you have more time in Oregon!). 

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There’s seriously SO much to do and see in Oregon, from watching sea lions lounge on oceanside docks to relaxing in hot springs tucked away in rain forests and a ski resort with the longest ski season in North America. So why should you trust me to know how you should curate your Oregon road trip?

My husband, Justin, and I live just a few hours from Oregon in Washington state and, as avid RVers, travelers, and hikers, we’ve taken more road trips than I can count to this magical state. In fact, we often joke that we’ve seen and done more stuff in Oregon than we have in our home state (Oregon is seriously so cool, guys!). 

Oregon coastline near the Heceta Head Lighthouse

So, during our years in the Pacific Northwest, we’ve traveled all over the state and have sniffed out the very best stops if you have a limited amount of time here. 

What that, let’s get into it!

One Week Oregon Road Trip Itinerary

Day 1: Leave Portland, explore the Columbia River Gorge, head to Hood River

Day 2: Leave Hood River, with stops at Mount Hood and Smith Rock State Park, head to Bend

Day 3: Explore Bend and head to Crater Lake National Park

Day 4: Explore Crater Lake National Park, hit Umpqua Hot Springs, and head to Eugene

Day 5: Head to Silver Falls State Park and end in Pacific City

Day 6: Explore Pacific City and head to Cannon Beach

Day 7: Leave Cannon Beach and head back to Portland

Woman sitting on the edge of Umpqua Hot Springs in Oregon

I’m going to dive deep into this road trip itinerary and will provide some additional suggestions later in the article if you’re lucky enough to have two weeks of adventuring around this incredible state.

First, though, let’s talk about some of the nuts and bolts of planning a road trip here.

Where should I fly into and out of for an Oregon road trip?

While there’s a number of smaller airports sprinkled throughout Oregon, all of them are teeny tiny, but for Portland International Airport, located in the biggest (and most hipstery) city in the state. You’ll have the best luck finding affordable airfare there (I use Skyscanner to find the lowest fares!), plus it’s a clean, well-organized airport and you’ll have decent car rental options. 

Portland also is a fun and vibrant city (soooo much good beer and donuts!) and is conveniently located near some of the most unmissable stops in Oregon, like the coastline, the Columbia River Gorge, and Mount Hood. Accordingly, I’d recommend starting and stopping your road trip here.

Woman walking in front of the Portland, Oregon sign

If Portland doesn’t work out for you for some reason, there’s a few other options in Oregon you might consider looking into, like the Bend Municipal Airport or the Eugene Airport. Honesetly, though, it may instead make more sense to fly into Seattle, which is only about two and a half hours north of Portland—and, on a road trip, what’s a few more hours in the car!

Do I need a car for an Oregon road trip?

Well, it’s a road trip, so yes, you’re going to want to rent a car.

If you can’t swing a rental car for whatever reason, there are definitely some cool trips you can do solely using public transit from Portland, such as to the adorable town of Hood River or to the Northern Oregon Coast. But if you want to maximize the amount of state you can see in a week’s span, renting a car will definitely be key.

Couple sitting on top of a black SUV in the Painted Hills of Oregon

If you’re reallllly looking to lean into those Pacific Northwest vibes, you could even consider doing a vanlife road trip here (after RVing all around the state, I can confirm that it is a dream!). Escape Campervans is an awesome campervan rental company with a pickup location in Portland, whose customized vans come with comfy beds and full kitchen setups.

When is the best time to go on an Oregon road trip?

The best time to go on an Oregon road trip is summer through mid-fall, when the temperatures are pleasant, the skies are clear, and all of the state’s high elevation hiking trails are free of snow and ice. That being said, this is far and away the most popular time to visit, so be sure to book your airfare, car rental, and accommodations far in advance to get the best prices. 

Couple walking in front of Ramona Falls in Oregon

While the weather along the Oregon Coast stays pretty moderate throughout the year, it can get quite wet and foggy in the wintertime. And as you move farther east along the coastline, the temperatures will plummet around the state in the colder months, with snow and ice making many of the beautiful mountains inaccessible and the roads straight-up sketchy. If you do visit during this time period, I’d suggest concentrating your trip along the Oregon Coast to minimize the impacts of the wintertime grossness as much as possible. 

Spring in Oregon is often usually pretty soggy and gray. The benefit of all that rain, though, is that its waterfalls will be flowing at their maximum volume and by late spring, the wildflowers will be in bloom. However, given the gnarly weather and the fact that high elevation hikes will still be inaccessible, this definitely wouldn’t be my first choice of when to visit!

South Falls in Silver Falls State Park in Oregon

How long do I need for an Oregon road trip?

One of the most important things to understand when you’re planning this kind of trip is that Oregon is HUGE, clocking in as the ninth largest state and encompassing almost 100,000 square miles (which is larger than the entire United Kingdom). So it’s going to be kind of  impossible to explore the entirety of the state during your allotted PTO this year. 

That being said, I’d make the argument that the northwestern quarter of the state has the highest concentration of jaw-droppingly awesome things to do here, so if you concentrate your road trip in this section, you’ll be able to hit a lot of the highlights within a week’s span.

Woman standing in front of Mount Hood in Hood River, Oregon

Get ready, though–your days will DEFINITELY be jam-packed; you’ll be doing a LOT of driving (although if you follow the Oregon road trip itinerary below, you’ll never drive more than four hours in any given day!); and you won’t be able to spend a ton of time at any one spot.

If you have a bit more time, like between 10-14 days, your schedule won’t be quite as crazy packed and you’ll even be able to squeeze in a few extra stops along the way (which I recommend below!).

Stops for a One-Week Oregon Road Trip Itinerary

Okay, now let’s chat about all the fun stuff you’re going to see as you explore this incredible state. Buckle up!

Day 1: Leave Portland, explore the Columbia River Gorge, head to Hood River

Total drive time: One hour (62 miles)

  • Portland has SO much good coffee and donuts, so before you leave on your epic road trip, be sure to fuel up with some! My favorite coffee shops in Portland are Never Coffee, Heart Coffee, or Oracle Coffee Company. It’s also basically legally required to get artisanal donuts whilst in Portland, so pick a few at Doe Donuts before you hit the road!
Woman holding box of Doe Donuts in Portland, Oregon
  • Once you’re good, caffeinated, and carbed up, you’ll start driving along the stunning Historic Columbia River Highway. Snaking along the Columbia River Gorge, this stunning 80-plus mile long canyon (with walls stretching up to 4,000 feet!) offers lush temperate rainforests and so many waterfalls (over 90 on the Oregon side alone!) in its expansive footprint.

    Pick and choose which stops you want to see along the way but some of my favorites include (heading from Portland east to Hood River): 

    Latourell Falls: You can see this 224-foot waterfall, cascading down a cliffside of columnar basalt, by simply walking just a few steps from the parking lot. Alternatively, if you’re feeling like getting a bit of a hike in, you can see this stunning waterfall if you follow along this 2-mile loop trail.

    Bridal Veil Falls: Just 5 minutes down the road from Latourell, Bridal Veil is a 120-foot two-tiered waterfall, cascading over an impossibly lush canyon.

    There’s an easy 0.4-mile upper interpretive trail that leaves from the parking lot that provides gorge-ous views over the Columbia River (get it?!), but if you’re interested in seeing the falls themselves, you can hike to the base of the waterfall along the 0.5-mile lower trail instead.

    Multnomah Falls: Regardless of which other waterfalls you choose to explore today, Multnomah Falls almost has to be included on your Oregon road trip itinerary. In fact, it holds the impressive title of the tallest waterfall in the state, at a whopping 620 feet tall!

    If you’re feeling like getting your hike on here, there’s a couple different options for you, ranging from a 0.2-mile trail to the bridge overlooking the falls to the incredible 5.1-mile Wahkeena Falls Loop Trail, which passes an eye-popping eight named waterfalls!

    Psst… you’ll need a timed permit to visit Multnomah falls from May through September, which you can pick up here.

    Wahclella Falls: This 115-foot two-tiered waterfall, dropping dramatically into a lush gorge, is an absolute stunner and accessible via an easy 1.9-mile trail.

    Punch Bowl Falls: If you’re looking for a slightly longer trail (and less crowds), Punch Bowl Falls is an excellent option. Along this 4.8-mile hike, you’ll pass dramatic basalt cliffs, trees dripping with neon green moss, and the eponymous waterfall, pouring into a bowl-shaped pool. Punch Bowl is frequently included in postcards for Oregon and it’s easy to see why.
Tip: Word of warning- several of these falls, especially Bridal Veil and Wahclella, are known for frequent car break-ins. Be sure to bring anything of value with you on your hike.
  • If you want to stop for lunch along the way, consider checking out some of the local eateries in the small town of Cascade Locks along the Columbia River Gorge, like the Thunder Island Brewing Co. for elevated bar food, or the Cascade Locks Ale House for a mean slice of pizza.

    If you’re visiting from August through November, swing by the Bonneville Dam to see chinook and coho salmon impressively fighting their way up the fish ladder to spawn.

    Once you’re done gawking at the salmon, consider grabbing some ice cream from the adorable Sugarpine Drive-In. Okay, okay- so you’d totally have to drive out of the way for this one, but their ice cream is ON POINT and they have a bunch of fun toppings, like cardamom graham crunch or pistachio meringue.
Ice cream sundae at Sugarpine Drive-In in Oregon
  • Finally, wrap up your day by heading to the charming town of Hood River.

    There’s tons of things to do in Hood River, from perusing the charming shops in its downtown to watching the windsurfers along the Columbia River (Hood River is considered to be the windsurfing capital of the world!) and checking out the many local breweries.

    My favorite spot for dinner is pFriem Family Brewers, which has a stellar outdoor space with river views. You can expect stick-to-your-ribs bar food, with a global twist, and REALLY good beer. 
Woman looking across the river at Mount Hood in Oregon

Stay at:

  • Best Western Plus Hood River Inn: Okay, this has to be the nicest Best Western, with a hot tub overlooking the Columbia River Gorge and a seriously good breakfast spread.
  • Columbia Gorge Hotel & Spa: If you like something with a bit more character than the Best Westerns of the world, Columbia Gorge Hotel feels like someplace that Hemingway would hide away in to write a novel. This 102-year old hotel perfectly melds modern amenities with historic quaintness and charm and its property is straight up gorgeous, with seven acres of gardens and its very own 208-foot waterfall.

Day 2: Leave Hood River, with stops at Mount Hood and Smith Rock State Park, to Bend

Total drive time: 3 hours (152 miles)

  • Grab some breakfast in Hood River (Kickstand Coffee and Kitchen makes a killer latte), and hit the road. 
  • First stop on the second day of your Oregon road trip- exploring Mount Hood!

    You’ll drive a little under an hour from Hood River to Tom, Dick, and Harry, a challenging 9-mile trail to an exposed ridge, offering in-your-face views of Oregon’s tallest and most famous mountain. It’s sooo stunning (especially at sunrise, if you don’t mind waking up, like, reaaaaally early!) and easily one of my very favorite Mount Hood hikes.

    If you don’t want to dedicate such a large chunk of your day to this hike (or just don’t feel like hiking 9 miles), I totally get it. Instead, you can do the more moderate 4.2-mile hike to Mirror Lake (which follows along most of the same trail as Tom, Dick, and Harry), where you’ll trek to an alpine lake that perfectly reflects the 11,249-feet tall Mount Hood on still mornings.

    For an even easier option, the 1.9 mile Trillium Lake is another excellent option right nearby, which you can literally just drive up to or explore a short and flat wooden boardwalk along its shoreline.
Couple sitting and overlooking Mount Hood at sunrise in Oregon
  • Stop in Government Camp for lunch—Mt. Hood Brewing Co. makes a mean burger and fries (I promise not to only recommend eating at breweries throughout this guide, but, c’mon- we are in Oregon, y’all!).
  • Continue to head approximately two hours southwest to Smith Rock State Park. It’s WILD to me how different Smith Rock looks, with its desert canyons and rugged basalt rock formations, than the alpine wonderland you just explored this morning in Mount Hood. 

    Smith Rock is actually a rock climbing mecca AND the birthplace of sport climbing in the United States. So if you happen to be a rock climber, now is your chance to take on one of the most famous climbing spots in the country!

    Not into scaling walls of rock hundreds of feet in the air? Yeah, me neither.

    Instead, you can simply watch the climbers from the ground as you walk along one of the best Smith Rock hikes, like the flat 1.3-mile Canyon Trail along the Crooked River or the 1.0-mile Rim Rock Trail, which, true to its name, follows along the rim of the canyon.

    If you’re up for more of a challenge, you can get the park’s most iconic view at the top of the aptly-named Misery Ridge Trail. While the trail is only a little over two miles roundtrip, you’ll climb over 1,000 feet in the first half. Thankfully, though, the reward is worth it, with stunning vistas of the Crooked River below and beyond, Smith Rock’s rugged rock formations.
Basalt rock formations at Smith Rock State PArk in Oregon
  • Finally, head to the fun town of Bend for the evening. Justin and I always joke that Bend is an outdoorsy hipster’s dream, with an adorable downtown, full of record shops and yoga studios, and with easy access to pretty much any outdoor sport you can think of. 

    For dinner, Bend is the birthplace of the Deschutes Brewery (try the pizza!). Spork is also a popular choice, with delicious Asian fusion dishes (see, I promised not to just recommend breweries!). Cap off your night with a scoop of gelato from Bonta and call it a day!

Stay at:

  • The Oxford Hotel: This is one of the best boutique hotels in Bend, with a stylish interior and thoughtful details throughout, like an in-room French press and hot tub to soothe those aching muscles from all that hiking!
  • Juniper Preserve: If you’re looking for a bit of luxury, this upscale resort undoubtedly has it, with an onsite spa, TWO outdoor pools, and sweeping views of the surrounding high desert landscape.

Day 3: Explore Bend and head to Crater Lake National Park

Total drive time: 2 hours and 45 minutes (102 miles)

  • Kick off your morning at A Broken Angel, a vegan food cart in Bend dishing out seriously tasty Southern and Mexican-inspired breakfast items.
  • If you didn’t get a chance to mosey around Bend’s charming downtown the night before, take an hour or two to browse the cute stores and boutiques around its main drag.

    Alternatively, if it’s hot, consider renting an inner tube from any of the rental shops in town and floating down the Deschutes River. When Justin and I visited Bend, we had an absolute BLAST floating down the Deschutes, especially through the Bend Whitewater Park section. This area of the river has different intensities of waves and rapids that you can bump your way down. In fact, there’s such large waves, you can watch literal surfers here throughout the year!
Woman kayaking down the Deschutes River in Bend, Oregon
Pssst…. we used our inflatable Intex K2 Explorer kayak on the Deschutes. We love this little guy because it’s super easy to store in the trunk of our SUV and whip it out when we get stumble across a lake or river we want to explore. If you’ve wondered whether inflatable kayaks are worth it, check out our Intex K2 Explorer kayak review.
  • Before you leave the Bend area, drive out to the gorgeous Tumalo Falls, a 97-foot waterfall tucked away in the Deschutes National Forest.

    There’s a variety of ways to enjoy the falls, including from a viewpoint just a few steps from the parking lot to a 0.6-mile roundtrip hike to a viewpoint directly overlooking the falls. There’s also a really lovely picnic area with a stunning view of the falls, so consider packing your lunch.
Tumalo Falls outside of Bend, Oregon
  • Make your way two and a half hours south to Crater Lake National Park, which holds the title of the deepest lake in the United States and is considered one of the 7 Wonders of Oregon.

    It will likely be late afternoon by the time you get there—if you’ve got the energy, climb up the 0.8 miles to Watchman Peak, widely regarded as the best spot in the park to watch sunset over the epically blue lake. Just don’t forget a headlamp for the hike down!

    If you’re not quite up for that, head to the Cloudcap Overlook on the east side of the lake, to watch the sun sink beneath the crater walls. This lookout is the highest overlook you can reach in the park by car, sitting at 7,685 feet above sea level, and provides one of the most expansive views over the lake.
East rim of Crater Lake National Park in Oregon at sunset
Pssst… Crater Lake is one of the snowiest places in the U.S., receiving up to 43 feet of snow annually. Because of this, most of the trails and facilities will be closed from November through June each year.
  • To be honest, Crater Lake is pretty remote and dinner options (especially those that are open post-sunset) are pretty slim. Check out the park’s Annie Creek Restaurant for a menu of standard soups and sandwiches and you may (or may not) be pleasantly surprised!

Stay at:

  • Crater Lake Lodge: You can actually stay right on the rim of the 7,700 year old lake in this cozy lodge. The Crater Lake Lodge is a bit on the rustic side, but it more than makes up for it with its proximity to the lake (uh, it’s literally on TOP of it!) and spectacular views.
  • Aspen Lodge: A comfy inn, run by a sweet couple, who are SO committed to you having a good time while you’re at Crater Lake. They have everything their guests could possibly need for outdoor adventures- snowshoes, kayaks, you name it!

Day 4: Explore Crater Lake National Park, hit Umpqua Hot Springs, and end in Eugene

Total drive time: 3 hours and 25 minutes (173 miles)

  • Spend the morning exploring some more of Crater Lake National Park

    Some nice, easy trails with spectacular views include the Sun Notch Trail, a 0.8 loop to a viewpoint overlooking Phantom Ship Island (which, true to its name, is a rock formation that looks a ship emerging out of the lake, that should be captained by ghost pirates) or the Discovery Point Trail, an easy trail that follows along the rim of the crater and offers beautiful views of Wizard Island in the center of the lake.

    If it’s summertime, one of the coolest things you can do (maybe quite literally!) is hike down the Cleetwood Cove trail and jump into the water of the deepest lake in the United States. Be prepared, though- the surface of the water is usually no more than a frosty 57 degrees or so, even in the summertime! While jumping in the water may cool you down real quick, the 700 foot climb back up to the rim will definitely get you warmed up again in no time!
Pine trees along the slopes of Crater Lake in Oregon
  • Grab a quick sandwich at the Rim Village Cafe and make the hour-long drive northwest to the lush Umpqua National Forest

    Here, you’ll make the 0.8-mile (roundtrip) hike to Umpqua Hot Springs, one of the most stunning series of hot springs in Oregon, tucked into a dense pine tree forest and carved into a cliffside overlooking the Umpqua River. You’ll find the warmed hot spring at the top of the cliff, with the pools becoming increasingly cooler as you get closer to the river.

    Word of warning- it’s pretty common for folks to soak in the nude here, so don’t be taken aback if you happen to see any surprise genitalia!
Couple sitting in Umpqua Hot Springs with pine trees in the background in Oregon
  • As you leave Umpqua Hot Springs, you’ll pass Toketee Falls on your way back to the Umpqua Highway, which is worth a stop if you’re still doing good on time. This is an easy 0.9-mile (roundtrip) trail to overlook one of the most stunning waterfalls in Oregon, surrounded by lush greenery and careening 120-feet down a columnar basalt cliff.
Tokotee Falls in Oregon
  • Drive two and a half hours northwest to your home for the evening, Eugene. This city is often overlooked for cities, like Bend or Portland, but it’s nevertheless quite charming, in my opinion, with old-school hippie vibes. 

    It also happens to sit at the southern end of the Willamette Valley, which Time recently dubbed “the next Napa.” Accordingly, you’ll find an INCREDIBLE food and wine scene here. If you happen to get to Eugene with some time to spare, consider checking out some of the best wineries in the Willamette Valley.

    For dinner, if you’re feeling a bougier option, Marche is an upscale restaurant with French influences and a seriously good wine list. If you’re not about that life, there’s also Tacovore, which, well, has tasty tacos!

Stay at:

  • Inn at the 5th: One of the best boutique hotels in Eugene, with stylish design, impeccable staff, and super comfy beds.
  • The Gordon Hotel: This art-filled hotel is conveniently located near some of the city’s best bars and restaurants. Plus it offers one super important perk- freeeee snacks in the lobby!

Day 5: Head to Silver Falls State Park and end in Pacific City

Total drive time: 3 hours and 10 minutes (159 miles)

  • Grab a quick breakfast and coffee at the Hideaway Bakery and make the hour and 20 minute drive to Silver Falls State Park, east of the capital city of Salem.
  • Silver Falls State Park is breathtakingly gorgeous, with huge primeval ferns and towering trees, dripping with moss. It looks exactly what you’d picture if you’d imagine the Pacific Northwest—in fact, it was the lush setting of the Twilight movies!

    Here, you’ll find the Trail of Ten Falls, which is one of the coolest hikes in Oregon. Beyond being nestled in a verdantly green temperate rainforest, with dramatic basalt cliffs, the hike, true to its name, takes you past ten waterfalls—four of which you can actually walk behind! I kept freaking out during this hike out of sheer happiness–it literally feels like something you’d experience in Iceland or something!

    To see all of the ten falls, you’ll hike along a moderately challenging 7.4-mile loop trail.

    But one of the amazing things about this trail is that it’s kind of a choose-your-own-adventure. You can easily hike as little as 0.4 miles to the South Falls (and still get to hike behind an enormous waterfall!) or hike along smaller portions of the loop (like hiking from the South Falls parking lot to the South Falls and Lower South Falls and looping back along the Maple Ridge Trail). Or hike the full loop—Oregon is your oyster! 

    If you wanna learn more about the different options on this hike, I’m kind of a little obsessed with it and wrote a whole article all about the Trail of Ten Falls.
Woman standing behind a waterfall along the Trail of Ten Falls in Silver Falls State Park in Oregon
  • Hop back in the car and loop down southwest to Pacific City, along Oregon’s famed coastline. You made it, baby!

    Spend the rest of the afternoon and evening enjoying this tiny, yet charming beach town. The best thing to do here is to enjoy the iconic Pacific City Beach, with its 327-foot sea stack, Haystack Rock, towering off in the distance.

    In fact, one of my favorite things to do on the entire Oregon Coast is to have a campfire directly on the sands of Pacific City Beach while watching the sunset (straight up MAGIC, y’all!). Just be sure to check that there’s no fire restrictions in place before lighting up.
Couple having a campfire on Pacific City Beach in Oregon at sunset, with Haystack Rock in the background
  • For dinner, grab food and a beer at Pelican Brewing, which is quite literally directly on the sands of Pacific City Beach. End the night by enjoying the salty ocean breeze on your face and the cold beer (or homemade root beer!) in your hand.

Stay at:

  • Surf & Sand Inn: I try not to play favorites with hotels, but if I had to, the Surf & Sand Inn would have my heart. This little motel has been providing lodging for visitors since the 1940s and retained all of its retro beach-y charm, just with updated clean and modern amenities. Plus it’s just a few blocks from the beach!
  • Headlands Coastal Lodge & Spa: For something a bit more upscale, Headlands is as close to Pacific City Beach as you can possibly be, without being, like, on top of Haystack Rock. The hotel offers a hot tub directly overlooking the iconic sea stack and you’ll have access to a variety of luxurious perks, like a welcome glass of curated wine.

Day 6: Explore Pacific City and head to Cannon Beach

Total drive time: One hour and 53 minutes

  • Start your day with breakfast at Stimulus Coffee + Bakery, which offers cool beachy vibes and a variety of food offerings for everyone, including our vegan and gluten-free friends. 
  • Explore a bit more of Pacific City, by hiking up the massive sand dunes of Cape Kiwanda to gape at its sandstone bluffs and the views of Haystack Rock. While the hike up the sand can be BRUTAL, there’s literally nothing more fun than sprinting down the dunes as fast you can on the way back down! 

    If you want another unique Oregon Coast experience, you can even drive on the beach that’s directly to the north of Cape Kiwanda, McPhillips Beach. You should definitely not do this if you’re using a rental car or if you do not have a four wheel-drive. Also, be sure that you check the tide tables to make sure you’re not driving on the beach at high tide—that would be quite the lasting memory of your Oregon coast road trip to get swept out to sea in your car!
Couple sitting on top of an SUV at McPhillips beach along the Oregon coast
  • Head north about 26 miles to Cape Meares State Scenic Viewpoint, which has a LOT going for it in its tiny footprint. There’s a lighthouse, built in 1890, just steps from the parking lot, which you can actually explore inside during the summer months; an “octopus” tree, with unusually arched branches, due to its usage in Native American burial rituals; and the largest spruce tree in the state, measuring 144 feet tall and a whopping 48 feet in circumference!
Man standing next to Cape Meares lighthouse along the Oregon coast
  • Continue your way north to Oswald West State Park, which stretches along four miles of the rugged coastline. You can stop at the park’s Short Sands Beach, to watch the surfers that flock here, due to having one of the best surf breaks in the state, or explore any of the hiking trails that snake through its temperate rainforest, like the Elk Flats or the Cape Falcon Trail.  
Man standing on Short Sands Beach along the Oregon coast
  • Continue north to one of my favorite Oregon Coast towns, Cannon Beach. This beach town offers a charming downtown, with cute coastal cottages, and one of the state’s most iconic beaches. You’ve almost surely seen it on Instagram, with its picturesque Haystack Rock (yes, another one), a 235-foot basalt sea stack that juts out of the Pacific waters below.
    There’s tons of things to do in Cannon Beach, from checking out its breweries (my forever favorite is Best Coast Brewing) to exploring its tidepools during low tide or having a campfire directly on the sands of the beach at sunset.

    For dinner here, check out Seasons Cafe, with classic staples, like soups and sandwiches, and where every single table has a jaw-dropping view of Haystack Rock.
Couple having a campfire on Cannon Beach in front of Haystack Rock in Oregon

Stay at:

  • Hallmark Resort and Spa: This family-owned hotel is basically as close as you can be to Haystack Rock and the staff are INCREDIBLE. You can enjoy an indoor hot tub, the luxurious spa, and best of all, freshly baked cookies at check-in.
  • Inn at Cannon Beach: Tucked away in a beautiful forested property and just the perfect distance from the bustle of the downtown area, this lodge kind of feels like a grown-up summer camp, complete with fire pits and smores. There’s definitely a few differences between the Inn and summer camp, though— the Inn’s building feels like the bougiest version of a cabin and the beds are as soft as a cloud.

Day 7: Leave Cannon Beach back to Portland

Total drive time: One hour and 45 minutes (82 miles)

  • Grab coffee and a freshly baked pastry from Insomnia Coffee Company and drive 10 minutes north to Ecola State Park.

    You’ll find miles and miles of some of the best hikes near Cannon Beach here, like the Indian Beach Trail, which leads you to a craggy beach that, like Silver Falls State Park, also was a filming location for the Twilight movies, or the Crescent Beach trail, where you’ll take a path winding through a coastal forest to a secluded beach.
Man standing on a stairs overlooking Crescent Beach in Ecola State Park in Oregon
  • Drive one hour and 35 minutes back to Portland, the very last leg of your trip. 
    If you have time to explore the city some, I’d suggest checking out the Portland Japanese Garden, which includes an authentic Japanese tea house and unparalleled views of Mount Hood. Alternatively, for a free botanical experience, the International Rose Test Garden, the oldest continuously operating rose test garden in the country!

If You have More Time on Your Oregon Road Trip

If you have some extra time to explore this incredible state, here are a few of my other favorite stops that you can add into your itinerary.

  • Painted Hills: True to their name, the Painted Hills of Oregon are rolling hills, with vibrant stripes of reds, oranges, greens, and blacks. There’s several easy and short trails here, where you can gaze at the surrounding hills’ vibrant hues, caused by climate change that happened in this area about 30 million years ago.
Green and red striated hills at the Painted Hills of Oregon
  • McCredie Hot Springs: Tucked away in the pine tree forests of Willamette National Park, you’ll find this beautiful series of pools, where you can relax in geothermally heated water and soak in the surrounding natural beauty. It’s a little confusing to get here, though, so, before you head here, be sure to read our post all about how to get to McCredie Hot Springs.
  • Tamolitch Blue Pool: This hike, also in the Willamette National Forest, takes you to a cliff overlooking the most stunningly colored blue pool I’ve ever laid eyes on. No, seriously–the water is the color of antifreeze. It gets its unusually blue color from extremely frigid groundwater that bubbles up through the volcanic rock here, which acts as a natural filter.
View of the Tamolitch Blue Pool in Williamette National Forest in Oregon
  • Depoe Bay: Known as the “Whale Watching Capital of Oregon”, Depoe Bay, found along the coastline, is one of the best places on the planet to see gray whales. There’s a number of Depoe Bay whale watching companies, including Whale Research EcoExcursions, which will take you to get up close and personal with these school bus-sized creatures, usually from mid-March through the beginning of October.

    Plus, you can check two items off your bucket list at once- these tours depart from the Depoe Bay Harbor, which is actually the smallest natural navigable harbor on the planet!
  • Astoria: This town, which has a unique mix of industrial and artsy vibes, sits along both the Pacific Ocean and the Columbia River. It’s where the 1980s classic, The Goonies, is set (let’s all do the Truffle Shuffle in Chunk’s honor)- and you can actually visit The Goonies house or the jail cell where the bad guys escape out of at the beginning of the movie in the Oregon Film Museum.

    If you have no idea what the Truffle Shuffle is, Astoria also happens to be home to Fort Stevens State Park, which has the skeletons of the Peter Iredale, a boat from the early 1900s, that wrecked on the park’s sandy shores.
  • Samuel H. Boardman Scenic Corridor: If you like dramatic coastline and rugged cliffs, you’re going to LOVE this park, which, dare I say it, offers the most stunning section of the Oregon coastline. In this little slice of heaven, you’ll find the Instagram-famous Natural Bridges, a sea arch that you can actually walk over (it’s preeeetty sketchy, though, so be careful!) and several other gorgeous spots, like Secret Beach or Whaleshead Beach. 
Sea stacks at Samuel H. Boardman Scenic Corridor in Brookings, Oregon

Two-Week Oregon Road Trip Itinerary

Want an idea of how to spend two weeks on the road in this magical state? I gotchu.

  • Day 1: Arrive in Portland, explore the Columbia River Gorge, and stay in Hood River
  • Day 2: Explore Mount Hood and head to Smith Rock State Park, stay in Bend
  • Day 3: Explore Bend and make a side trip to the Painted Hills, stay in Bend
  • Day 4: Head to Crater Lake National Park
  • Day 5: Head to Umpqua Hot Springs, Terwilliger Hot Springs, and stay overnight in Silver Falls State Park
  • Day 6: Explore Silver Falls State Park and head to Florence
  • Day 7: Explore Florence, head to Cape Perpetua and Heceta Head Lighthouse, stay in Newport
  • Day 8: Explore Newport, drive to Lincoln City
  • Day 9: Explore Lincoln City, drive to Pacific City
  • Day 10: Explore Pacific City and Cape Meares, stay in Cannon Beach
  • Day 11: Cannon Beach, head to Astoria
  • Day 12: Explore Astoria, head to Portland
  • Day 13: Portland
  • Day 14: Portland, fly home in the afternoon/evening
Haceta Head Lighthouse, perced on a cliff, along the Oregon coast

Well, my friend, you now have the tools to have the most epic Oregon road trip possible. Do you have any questions about the suggested stops above or the itinerary? Let me know in the comments below!

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2 thoughts on “Oregon Road Trip Itinerary: One Week (or More!) in the Pacific Northwest’s Paradise”

  1. I wanted to thank you for this blog post. My friend and I are from FL and CA, respectively, and we followed a lot of your journey recs. Went counterclockwise and had a wonderful time this early September week.

    I offer you two additional recs.

    River Rafting White Salmon River outside Hood River with River Drifters, and Tamanawas Falls hike between Hood River and Mt Hood. Both are good for intermediate-level folks.

    Oregon over-delivered, and your blog helped us navigate!


    • Aw, this makes me so happy! Oregon is one of my absolute favorite states, so I’m glad you guys had a blast.

      We’ve done Tamanawas Falls and I totally agree it’s an awesome option near Hood River, but we’ll definitely have to add rafting the White Salmon River to our bucket list. That sounds AWESOME!

      Thanks for reading (and for the sweet compliment- it made my day!) and happy travels.



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