How to Plan an Amazing Oregon Road Trip: A Complete Guide

The rugged coastline of the wild Pacific Ocean; thundering waterfalls surrounded by dense, green forests; soaring, high-desert volcanic basalt towers. Couple these diverse geographical regions with vibrant city stops and you’ve got yourself one amazing Oregon road trip.

Few states let you experience this many different ecosystems so close together. With a home base in Portland and a couple weeks to hit the road, you’re sure to fall in love with Oregon.

And who better than a lifelong Oregonian to lead you on this adventure! I’ve been all over this beautiful state and my favorite way to travel is by car or my own two feet. I’ll give you the lay of the land then give you a few options for your Oregon road trip itinerary.

Disclaimer: Some of the links in this post, like hotel and vacation rental links, are affiliate links, meaning at no additional cost to you we make a little bit of money if you click through and book. That being said, we would absolutely never recommend something to you that we don’t stand behind 100%.

Where to Start and End Your Oregon Road Trip 

Well, that depends on where home is. Portland is ideal if you’re local, coming down from Washington, or are flying in.

It’s a great home base to leave from and return to, and if you need to rent a car for your drive you’ll have the best choices here. Fly into Portland International Airport (PDX), which is just outside the city center. Check flight prices for your dates here, and rental car options here

If home is California, you may choose to start at a city in Southern Oregon (like Ashland off the 5), so you have a shorter drive back home. 

We’ll lay out the major sections of the state so you can customize your Oregon itinerary to best meet your needs.

How Many Days Do You Need? 

This is a tough one because ideally you can dedicate a whole month to exploring the state (but we realize few people have this kind of luxury). 

With that, we’d recommend at least 10-14 days to hit many of the standout locations and not feel too rushed to move on to your next destination. The day-by-day Oregon road trip itinerary below is for 14 days, but we have not one, but TWO options for 10 days too. 

If you have less than two weeks, you can do most of the coast and central loop, which are our favorite parts of Oregon. 

That said, it also depends on what you’re looking for out of your trip. If you want to explore cities and wineries and prefer plusher accommodations (ie. not camping), you could make an awesome 10 day trip making your way from Portland down to Ashland.

The Route 

We think the best way to do this road trip is essentially a huge loop, starting and ending in Portland, completing the coastal and central routes. To do the whole loop, you probably need 14 full days. But, before we jump into your day-by-day itinerary, let’s review some basics about Oregon geography and how best to get around. 

Here’s a helpful map for the road trip itinerary you’re going to find below. 

It’s helpful to think of Oregon in terms of three main thoroughfares: The coastal route, the I-5 route, and the Central Oregon route.

Each offers something unique and while you can (and should) explore them all, you probably don’t want to keep jumping back and forth between them. To streamline your itinerary, get all your coast stops done in one go, then your I-5 stops, then central Oregon. 

Coastal Route: Astoria to Brookings

The Oregon Coast is unique in that the public enjoys access to all 363 miles of it—regardless of private ownership—thanks to the 1967 Beach Bill. This means you can explore every tidepool, beach, and dune as far as you can see. I’ll lay out this route from north to south as if you’ll be driving the whole thing (which would make an awesome road trip in itself).

Highlights of the Oregon Coast 

  • Astoria (95 miles from Portland, 1 hr 45 min) – This northernmost coastal town in Oregon is the oldest settlement west of the Rockies and boasts a thriving fishing and commercial shipping industry, breweries and restaurants, sprawling parks and historical attractions like the Peter Iredale shipwreck

  • Cannon Beach (26 miles from Astoria, 40 min) – One of the most popular beach towns in Oregon that offers numerous shopping, dining, and lodging options with the imposing Haystack Rock holding it all in place.

  • Tillamook and Cape Kiwanda (40 miles from Cannon Beach, 56 min) – Home of the famous Tillamook Creamery and the spectacular Cape Kiwanda natural area for tidepools, sand dunes, and the rugged Oregon coastline.

  • The Oregon Dunes (140 miles from Tillamook, 3 hours) – Stretching over 40 miles, the Oregon Dunes provide phenomenal outdoor recreation (think dune buggies and ATV’s), camping, and sightseeing.

  • The Samuel H. Boardman Scenic Corridor (120 miles from the Oregon Dunes, 2 hr 20 min) – A 12 mile long state park with some of the most breathtaking coastal scenery on the west coast—Archrock, Indian Sands, and Cape Ferrelo are just a few of the wonders in this jam-packed corner of the world that will blow you away. Unfortunately, it’s a little out of the way, so if you also want to see places like Bend and Crater Lake, you’re going to have to skip this on the itinerary below (check out the 10 day itinerary to see how you could incorporate it). 

The I-5 Corridor

True, driving the I-5 corridor isn’t the most exciting in terms of sightseeing, but it does give you quick and easy access to the state’s biggest cities and serves as the main artery for most transit. You can drive the whole freeway in about five hours, but there are some noteworthy stops that will take you a little ways from the 5.

I should say upfront that if you have less than two weeks for your trip, it’s likely you won’t see much of this route as the other two are a better bang-for-your-buck.

Highlights of the I-5 Corridor

  • Portland – You can spend a lifetime in Portland (I have!) and never get bored—the food/coffee/hiking/beer/hipster mecca never fails to deliver.

  • Willamette Valley (37 miles from Portland, 45 min)- Portland and Eugene sit in the Willamette Valley, but usually when people talk of it, it’s in reference to its world-renowned wineries. Come for the pinot noirs, long rambling roads, and quaint small towns like McMinnville. 

  • Eugene (92 miles from McMinnville, 1 hr 30 min) – “Track Town, USA” is home to the University of Oregon, a thriving arts and outdoor scene, and an abundance of hippies. 

  • McKenzie River (54 miles from Eugene, 1 hr)- Lava flows, old growth forests, hot springs, crystal clear swimming holes—need I say more?

  • Ashland (230 miles from McKenzie River, 3 hr, 40 min) – Ashland is home to the Oregon Shakespeare Festival and people seriously come from all over to see shows there. It’s also an awesome town to visit in its own right with arts and culture, beautiful parks, and surrounding mountains.

Central Oregon 

The Central Oregon route takes you past some of the best scenery in the state as you start in the north from the breathtaking Columbia River Gorge, down past Mt. Hood, then skirt along the Cascade Mountain Range finally making it to Crater Lake. If you’re doing the trip in the winter, be prepared for snow as some of the passes will be obstructed. 

Highlights of Central Oregon

  • Hood River (62 miles from Portland, 1 hr) – A cute, hip town known for its wind surfing and beer—what’s not to love! It’s also a great jumping off point for Gorge adventures.

  • Mt. Hood (43 miles from Hood River, 54 min) – Skiing, snowboarding, hiking, camping – Mt. Hood has it all no matter what time of year you visit. 

  • Bend & Smith Rock (106 miles from Mt. Hood, 2 hr) – Bend is the second fastest-growing city in the whole country, and is the hub of Central Oregon and people who love beer, food, and the outdoors (and you can’t leave without experiencing Smith Rock—more on that later!)

  • Crater Lake National Park (144 miles from Bend, 2 hr 45 min – Time and mileage depend on road closures) – Crater Lake is the only national park in Oregon and it attracts visitors from all over the country. As you might guess, it’s a giant lake (the deepest in the US) known for its crystal clear blue waters.

When to Do This Road Trip

This road trip can be accessible any time of the year if you’re flexible, and each season will offer something different. Since the geography is so diverse, we’ll break it down by route.

Coastal: Summer is definitely the best time to do the coast route for the most sunny(ish), dry(ish), and warm(ish) days, but you will be fighting crowds. Spring and fall can also be winners, but if you have bad luck you could spend all your time in the rain.

I-5 Corridor: With the exception of the Mackenzie River, most of the stops on the I-5 corridor are cities so you can really go anytime of year. Portland, Eugene, and Ashland are all incredible places to visit during the rainy, cold seasons with their abundant arts, dining, drinking, and entertainment options.

Central Oregon: If you’re a ski bum you’ll love traveling the central route in winter or early spring, though if there’s a lot of snow they’ll sometimes close the road up to Crater Lake. If you’re looking for more hiking and camping options, then summer or early fall will give you the best weather (Pro tip: September and even October can be the BEST for camping in Oregon because most of the mosquitoes are gone!).

The main route we’ll lay out for you below has you starting your road trip from Portland, heading down the coast and then up through central Oregon – and for this, summer will be your best friend. Most times between June and early October should fit the bill. 

Let’s Talk About Crater Lake 

Crater Lake is well worth a visit. If you have two weeks, definitely spend a night at Crater Lake, which puts you in prime position for exploring the park before and after the day trippers leave. 

But it is a bit out of the way if you only have 7 days.  With 10, you can do it as a day trip or as an overnight if you’re in the area (like in our 10 day itinerary at the end of this post). 

The Complete Guide to Planning a 14 Day Oregon Road Trip Itinerary 

When you’re on the road for 14 days we know that not everyone can afford to stay in a hotel every night, so I’ve done my best to give you camping, vacation rentals, and hotel choices so you can mix and match based on the weather, your mood, and your budget constraints. 

I’ve also thrown in a number of eating and drinking spots knowing full well that when you’re in road trip mode, there will be a significant number of PB&J’s eaten from the trunk of your car. You do you.

Day 1: Portland to Cannon Beach

Drive time: 80 miles, 1 hr 25 min

You’ll start off with an easy hour and a half drive to Cannon Beach. Leave as early as you can to enjoy the day at the beach and catch the sunset at Haystack Rock. For an extensive look at all Cannon Beach has to offer, check out my post here.

Road Trip Stops

The view of the Saddle Mountain summit

We’re including these places as stops that you should make over the course of the day of driving. 

Saddle Mountain One of my favorite hikes, like ever. 

Dairy Queen – Ok, so obviously you don’t have to stop at the DQ, but it was always a special treat to do so when I was a kid and we’d all get a chocolate dipped cone. If you’re road tripping with kids, maybe they’ll appreciate it as much as I did. Or you can just enjoy it as an adult, cuz you’re on vacation! (Note from Matt: GET AN OREO BLIZZARD THEY’RE THE BEST)

Things to Do in Cannon Beach

  • Haystack Rock – You can’t not see Haystack Rock when you visit Cannon Beach – it’s the 235 foot monolith just hanging out in the ocean right off the beach. Best viewed at sunset.

  • Ecola State Park – Try this 4.7 mile out and back to see the old-growth Sitka Spruce and explore the secluded Indian Beach.

  • Oswald West State Park – Oswald West has tons of trail and beach options, but Short Sands beach is one of my favorites. Great for a chill afternoon picnic or watching surfers.

  • Coffee at Insomnia, lunch at Seasons Cafe, and Bruce’s Candy Kitchen for well, candy!
Ecola State Park is well worth your time when you’re near Cannon Beach

Places to Stay in Cannon Beach

Wright’s for Camping – Located on the other side of the 101, but just on the other side and is actually really nice and it’s only a ten minute walk into town.

Surfsand Resort – Definitely pricier, but unbeatable location and nice rooms. 

Schooner’s Cove Inn – On the north end of town so it’s just far enough removed and it’s right next to Insomnia Coffeehouse.

Day 2: Cannon Beach to Newport

Drive time: 108 miles, 2 hr 30 min

You’ll be spending two nights in Newport, so take your time leaving Cannon Beach. If you opted for a hotel, sleep in and call the front desk for an extra hour before you have to check out, then head south.

Road Trip Stops

  • Hike to the top of Neahkahnie Mountain – I might go so far as to say if you’re only going to do one coast hike, it should be this one. There are a few different approaches ranging from three to right miles, but some close down periodically due to blowdown from storms. I’ve included the newest route here that clocks in at seven miles. The views are unbeatable if you can time it for a clear day.

  • Tillamook Cheese Factory – Ice cream! Squeaky Cheese! Cows! And a surprisingly decent lunch spot for such a popular tourist attraction. 

  • Stretch your legs and take in some great views at Cape Kiwanda.

  • Look down upon Devil’s Punchbowl as it churns up the sea, and explore the tidepools below, but ONLY AT LOW TIDE. Seriously, folks. 
Coastal views from Neahkahnie Mountain

Places to Stay near Newport

Agate Beach Motel – Aaaaahhhhhhhmazing views, nice rooms, and walking distance to Yaquina Head Lighthouse.

Inn at Nye Beach – An upscale hotel right on Nye Beach. It even has a fancy spa!

Rent this adorable beachfront cottage that sits about 10 minutes south of town, but since you’ll be in Newport for two nights you might like the solitude of a quieter beach right outside your back door!

Or try this romantic beachfront apartment that is close to everything. Did I mention the SOAKING POOL WITH OCEAN VIEW or the PRIVATE SAUNA?!?!

South Beach State Park – Incredible location for camping or yurt rentals.

Day 3: Newport

Exploring around the iconic Yaquina Bay Bridge in Newport

You’ve got a full day to get out and explore the central Oregon coast, so rise and shine and get going! You’ve got a lot to do today.

Things to Do in Newport

  • Oregon Coast Aquarium – Y’all this place opened when I was 11 and it was a BIG DEAL and I still can remember vividly being mesmerized by the hypnotic jellyfish tank. It’s a very cool aquarium. A great option for a rainy day.

  • Yaquina Head Lighthouse – Built in 1871, it’s the oldest original wooden lighthouse left on the Oregon Coast. There’s also cool tide pools nearby. A must-stop for photographers.

  • Ripley’s Believe It or Not and Louis Tussand’s Waxworks – You’ll either love or hate this recommendation, but this is JUST the type of place I keep my eye out for on a road trip. Tacky, kitchy, creepy, fun, and great photo ops. 

  • Grab coffee at the Coffee House, and a Spruce Tip brown ale at Wolf Tree Brewery.

  • Breakfast at Cafe Stephanie, dinner at Local Ocean (yes, it’s a splurge, but you won’t regret it).

Spend another night in Newport before moving on in the morning. 

Day 4: Newport to the Oregon Dunes

Drive time: 71 miles, 1 hr 35 min

You’re off to the ethereal Oregon Dunes, and the real question you need to ask yourself is: to dune buggy, or to not dune buggy? 

This is the largest area of coastal sand dunes in the country, and even if you’re just camping and exploring, you’re sure to love it. 

Note that some areas will be off limits due to nesting Snowy Plovers from March 31 to September 31, but I was there during this time and it was nbd.

Road Trip Stops

Thor’s Well and the Cape Perpetua Lookout – The lookout stands at 800 feet which doesn’t sound that high, but when you’re up there it feels like you’re at the top of the world. After taking in your views, visit the “Drainpipe of the Pacific”. Thor’s Well is very cool and very dangerous. Best viewed right before high tide

Thor’s Well is a sight to behold
The incredible coastal views from the Cape Perpetua Lookout

Heceta Head Lighthouse – About 15 minutes south of Cape Perpetua is the Heceta Head Lighthouse, and miles of good hiking trails all around. It’s a half mile climb up to the lighthouse, and the views are stunning. They even have free tours available from 11am to 3pm every day in the summer!

Things to Do in Oregon Dunes

Places to Stay near Oregon Dunes

Tahkenitch Campground – Either pitch a tent here, or hike a couple miles to Threemile Lake which makes a good destination for backpackers who want to immerse themselves in the scenery.

If you’d rather stick with a hotel, you’ll have to stay a bit north in Florence, or a bit south in Reedsport. You won’t find anything super fancy, but we’d recommend the Park Motel and Cabins just south of Florence for affordable motel or cabin accommodations.

Try this private chalet on 10 acres with a jacuzzi, outdoor fire pit, and lake views.

Days 5: Oregon Dunes to Eugene

Drive time: 89 miles, 1 hr 35 min

Say goodbye to the coast and hello to the Willamette Valley. You’re off to Eugene along OR-38, which follows the beautiful Umpqua river. There’s not really any stops to take except to admire the beauty around you, so take your time leaving the coast and maybe hit the river for a morning kayak session.

Places to Stay near Eugene

The Graduate Eugene is an awesome hotel choice for pretty affordable, hip rooms in a great location. 

This two bedroom house in west Eugene is close to dining options, or just one block from a local organic grocer for enjoying a quiet homemade meal out in the garden.

This delightful studio cottage is close to everything and a SUPER nice lady named Carol will be your host. You’ll be bff in no time. The pictures are, admittedly, not great. But the reviews are.

Still watching your budget? Try the Armitage Park Campground right on the McKenzie River and a ten minute drive to Eugene.

Day 6: Eugene

Spend the day in Eugene, a lively college town that’s full of underrated things to do, see, eat, and drink. 

Things to Do in Eugene

The view from Spencer’s Butte… ha. ha.
  • Saturday Farmers Market – Obviously, if you’re not in Eugene on a Saturday you’ll miss this, but if you are, go see the local stands, grab some grub, and stock up on car snacks. 

  • Hike Spencer’s Butte – This two mile hike up to a lookout over Eugene and the Willamette Valley makes for the perfect morning/afternoon/evening or whenever time!

  • Take a self-guided mural tour of the city with more than 100 gorgeous murals to find. 

  • Splurge on a meal and a fancy cocktail (like the bourbon & ginger) at Izakaya Meiji Company. Their ramen is bomb, but if you feel like going all out order as many small plates as you can.

  • Coffee at Wandering Goat, and brunch at Lion & Owl.

Day 7: Eugene to Toketee Falls

Drive time: 124 miles, 2 hr 10 min

Head south on the 5 then hang a left on the 138 till you get to the magical Toketee Falls—a 110 foot, two-tier waterfall on the Umpqua River.

Things to Do at Toketee Falls

  • Relax!

  • Hike to the waterfall, duh. It’s a very short trail in, but it’s usually not as busy as you might expect since it’s a ways from any big city.

  • Take a side trip to the clothing-optional Umpqua Hot Springs (which is also super fun to go to in the snow if you can get there!). Naked hippies abound. You’ve been warned. 

Places to Stay near Toketee

Camp at Toketee Lake just a couple minutes from the falls (note this is a dry campground so you’ll either have to cart your water in or come with a filtration system).

Or try nearby Poole Lake Campground for super nice sites and swimming and fishing galore.

Still wanting some luxury? A mere ten miles from the falls is Umpqua’s Last Resort, a very cool park that offers cabin, yurt, tiny home, RV, and glamping options!

The Steamboat Inn is another good option, with romantic suites (with kitchenettes!). It’s backtracking a bit – it’s 20 miles west of Toktee – but might be worth it if you’re looking for a special stay. 

Day 8: Toketee Falls to Crater Lake

Drive time: 71 miles, 1 hr 30 min

Depending on the time of year (and how much snow we’ve had), you may have to adjust your route since they’ll often close the north entrance to Crater Lake National Park in the winter months and into spring/early summer (I’m writing this at the end of May and it’s currently closed). Fingers crossed the north road is open, because it will shave off a lot of time for you. If not, don’t worry because the drive is beautiful and you’re on a road trip after all!

My number one tip for enjoying Crater Lake is to time your activities for the early morning and late afternoon/evening. This will help you avoid the throngs of afternoon day-trippers.

Things to Do in Crater Lake 

  • Hike Mount Scott, the highest accessible point in the park – Mount Scott sits at 8,938 feet and gives you incredible views of the lake and surrounding area. Since it’s so high up, it often doesn’t open until July, and even then you’ll likely encounter ice. There’s also little tree cover so wear a hat and go early in the morning if you can.

  • Drive the rim, preferably before 9am (which is when all the people show up).

  • Hike down to Cleetwood Cove, the lowest accessible point in the park. Do not be deceived by the short length of this trail—it’s hard but soooooo worth it. This is the only spot you have legal access to the shores of Crater Lake and you can (and should) take a quick dip in the water even though it’ll be very cold. 

  • If you stick around for sunset, make sure to catch it from Garfield Peak, a short three and a half mile hike to picture perfect views. It’ll be hard to leave once the sun goes down.

Places to Stay near Crater Lake

Crater Lake Lodge – You’ll need to book this well in advance (true story, people make reservations a year ahead of time). If you don’t get a room, you should at least go inside and look around!

Crater Lake campgrounds – There are two main campgrounds, Mazama and Lost Creek. Lost Creek is much smaller, only accommodates tent campers, and is all first come, first serve. If you’ve struck out on reserving a spot at Mazama and you can get to Lost Creek in the morning, you may be able to snag a spot. There are also cabin options at Mazama Village.

Diamond Lake Resort – A well-established lake resort that has motel, cabin, and studio options – all pretty darn close to Diamond Lake if you can’t secure one of the other places at Crater Lake. Tent spots are available at the Diamond Lake Campground.

Day 9: Crater Lake to Bend

Drive time: 144 miles, 2 hr 40 min

Before you head out of Crater Lake, I implore you to wake up early and do the Mount Scott hike if you haven’t done it yet. I can think of no better way to start my day, and when you hit Bend you’ll be more than ready for your local microbrew. 

Road Trip Stops

If you failed to follow my morning hike instructions, you can always redeem yourself by hiking Paulina Peak on the Newberry Crater. Sitting about 50 miles south of Bend is an active shield volcano, and on a crystal clear day from the highest point of Paulina Peak (just shy of 8,000 feet) you can see all the way up to Mt. Adams in Washington and down to Mt. Shasta in California. 

Places to Stay in Bend 

LOGE Bend – Offering gear rental, outdoor events, and in-room hammocks! Great for the adventure-minded traveler.

The Oxford Hotel – A swankier option that puts you right in the heart of downtown Bend.

Tumalo State Park Campground – A ten minute drive north of town, this campground is well-set up, has a fun atmosphere, and the Deschutes River flows right by it for an easy dip.

This historic cottage is just a few minutes walk to downtown and even has complimentary bikes for exploring the city!

This modern one bedroom apartment is near all of downtown’s shopping and dining options, but it also has a great kitchen if you’re feeling burnt out on restaurant life.  

Day 10: Bend

Bend is the hub of central Oregon, and you could easily spend a week or more here and still have plenty to do. But, since your life is the road, you’ve only got two days here, so you’ve got to make them count. 

Things to Do in Bend 

  • Beer! First things first, right? – Bend (and lots of Oregon towns) are known for their local beer selection, and Bend is no different. There are too many to list, so I’ll leave you with a few of my personal faves: Boneyard Beer (Diablo Rojo), Ale Apothecary (Farmhouse), and Crux (Cast Out IPA).

  • Hiking – Unsurprisingly, Bend offers some excellent hiking not far from the city. Here are a few options:
    1. Tumalo Falls – This 6.5 mile loop option takes you to a wide 97 foot waterfall. You can also drive straight to a much closer trailhead and only walk a few minutes to see the falls if you’re strapped for time.
    2. Green Lakes Trail (or the South Sister, if you’re feeling adventurous) – This is a long one, but not too difficult. Plus you can swim and there are camping spots at the lake if you want to make it an overnighter.
    3. Pilot Butte – Much shorter and easier and walkable from the Bend city center. A great morning hike before brunch.

  • Float the River – An oh-so-relaxing way to spend a sunny day. Park at Riverbend park, rent a tube, float on, hop out at Drake Park and either walk or grab a shuttle back to your car.

  • Eating  & Drinking: Thump for coffee, Chow for brunch, Spork for lunch/dinner. 

Day 11: Bend to Mt. Hood

Drive time: 106 miles, 2 hr

The drive time will depend on where you’re staying on the mountain, but you should plan on around two hours from Bend to Mt. Hood. You should also plan on waking up bright and early for your most important pit stop: Smith Rock.

Road Trip Stops 

Smith Rock State Park – If you’re a climber, you may need to change up your itinerary to spend more than half a day here, but for the rest of us it will suffice to hike the Misery Ridge Trail, and the best time to do it is in the morning. It gets hot and there’s little to no tree cover.

Things to Do near Mt. Hood 

The view from the top of Tom, Dick, and Harry Mountain just before sunset
  • Hike! – Check out our complete Mt. Hood hiking guide for a plethora of options. If I had to pick just one (oh man!) I’d say to do Tom, Dick, and Harry for a great workout and views for days!

  • Trillium Lake at sunset (or sunrise) – You don’t have to camp here to take in the sun rise/set, but it sure makes it easier!

  • Hang out with the local ski bums in Government Camp. Grab a burger and pint at Mt. Hood Brewing Co., or a schnitzel sandwich at Glacier Public House.
Trillium Lake at dawn

Places to Stay near Mt. Hood 

Timberline Lodge – This historic lodge was used for the exterior shots of the Overlook Hotel in The Shining (sadly there’s no hedge maze where a psychopath chases you around with a chainsaw, but you can still manage a good time on your own). 

Trillium Lake Campground – A beautiful and popular day-use and overnight destination for travelers. They always hold back some sites for first come, first serve.

Just a downright adorable cabin in the woods – This one-bedroom cabin sits on four private acres just outside of Rhododendron, putting you close to all your Mt. Hood needs.

This place is incredible and can sleep eight so call your Portland friends and have them come out to the mountain and meet you for the night. 

Day 12: Mt. Hood to Hood River

Drive time: 43 miles, 54 min

I know I’ve given this kind of recommendation a lot here, but I’m gonna do it again! I really think you should do a nice morning hike before heading up to Hood River. It’s only an hour’s drive so you’ve got time. Might I recommend Tamanawas Falls? It’s on the way! 

Road Trip Stops

Tamanawas Falls – This is the perfect pit-stop hike. You literally have to drive right past the trailhead to get to Hood River, it’s only 3.5 miles, and you get a 110 foot waterfall! Just do it. 

Drive the Fruit Loop! This 35 mile loop around the Hood River Valley takes you past 29 different vendors ranging from orchards and vineyards to bakeries to antiques. Eat your way through this gorgeous valley and stock up on fresh fruit and cider.

Places to Stay in Hood River 

Hood River Hotel – This reportedly haunted 1912 hotel is right in the center of town. Beware of room 310!

The Society Hotel in Bingen – If you can swing it, I can’t think of a better place to round out my two week road trip than in the tranquil Society Hotel. Rest your tired muscles in the spa then sip an old fashioned in their lounge.

This spacious two bedroom home has a gorgeous back deck and a view straight at Mt. Adams, just across the Washington border.

This one-of-a-kind, modern, window-wrapped guesthouse must be seen to be believed. 

Day 13: Hood River

Hood River is your last destination on this epic road trip, and it will send you off with a bang. This hip city on the Columbia River is world-renowned for its windsurfing but also offers up incredible hikes and top notch food, beer, and wine.

Things to Do in Hood River 

Day 14: Hood River to Portland (and the Gorge)

Drive time: 65 miles, 1 hr

On your last day in Oregon, head back towards Portland, where your road trip ends. There’s one major highlight left along the way, and that is the Columbia River Gorge.

Road Trip Stops

The Columbia River Gorge – Depending on how much time you’ve got before you make your way back into the real world, take in as much of the Columbia River Gorge as you can. Ideally, you’ll go on at least one hike, and bonus points if you can squeeze in a view and a waterfall. I’ve done an extensive post on the Gorge you can find here, but for this shrunken time frame you’ve got to be efficient so here’s what I’d suggest: 

  • Multnomah Falls (because you have to) – Leave early and see what all the fuss is about. Take the actually-tough mile hike up to the top. It’s worth it.

  • Hop on the Historic Columbia River Hwy that runs parallel to the 84, but will take you at a more leisurely pace. Take a quick pit-stop to see Wahkeena Falls, then keep going about three more miles till you get to the Angel’s Rest Trailhead.

  • Angel’s Rest – This out and back 5-miler will give you a condensed taste of what the Gorge has to offer, with an incredible payoff at the end. Plan to bring a snack or lunch up to the top, because you’ll want to linger.

Now—sigh—you’ve got to head back to Portland along the 84 as the Gorge slips away. Be a little sad. It’s okay.

Fly home.

Come back soon. 

More Great Stops in Oregon

Obviously you can’t see everything in 14 (or even 30!) days. In case you need to swap things around or alter your route, here are few options:


Astoria is a great stop if you can fit it in, or a nice weekend trip idea to keep in your back pocket. I make it a point to spend some time up there every few years.

There are tons of cool restaurants, breweries, and shops – and it has the best state parks on the coast. If you’re even a minor history buff, make sure you go to the Lewis and Clark National Historic Park for excellent trails and people that dress in old timey clothes doing old timey things like tanning hides and cobbling shoes.

Also, do not miss out on climbing the Astoria Column!

Silver Falls State Park and Opal Creek

This 7.8 mile loop trail takes you past all 10 of Silver Falls’ waterfalls and is just as spectacular as you might imagine. It’s almost always crowded during the summer months, but the trail is long enough that the crowds tend to thin out. Plus, if you’re out this way anyway, you should really stop by (and camp for the night) at Opal Creek. This creek runs through an old growth forest and has some of the most crystal clear (and freezing cold) pools you’ve ever seen. See it all with this 7 mile hike.

McMinnville and Willamette Valley

We highlighted McMinnville in our mini 7-day trip section below, and it’s a shame it couldn’t fit in every itinerary. But, if you have some extra time (or even a free weekend in the future), it makes for a great destination, especially for the wine lovers. Downtown McMinnville is super charming and the main drag is dotted with shops, restaurants, and just fun stuff to pop your head in and see. Expand your trip by visiting some of the surrounding vineyards. 


I love Ashland, but it is far away for this Portland dweller. The highlight of any Ashland trip is the Oregon Shakespeare Festival that runs much of the year with a break from November to mid-February. There are always more than enough plays to see, both Shakespearean and modern and you can often snag half price tickets day-of. If plays aren’t your thing you’ll still love the quaint downtown area and surrounding parks and nature trails.

Southern Oregon Coast

Like Ashland, the southern Oregon coast is also far and also wonderful. If you can find the time to make your way down there, you must, must, must spend time at the Samuel H. Boardman Scenic Corridor. Y’all—it’s just so flipping stunning! Start with the Secret Beach trail to whet your appetite. 

Alternate Itineraries: 7 and 10 Days

Now, we know that not everyone has a full 14 days to spend exploring Oregon. Here are some different approaches to planning an amazing trip to Oregon. 

With 7 days 

Seven days isn’t much when we’re talking about road trips, but we know the reality for most folks is that a week may be all you have. Never fear! You can still have a blast! Read below for our recommendation for a killer week-long road trip in Oregon.

Here, you really have to stay relatively close to Portland so you don’t feel too rushed. For this timeframe, I’ll give you two options: the westbound (focusing on the coast and the I-5 corridor) and the eastbound route (focusing on Central Oregon).

Option 1: The Coast and Wine Country

The loop: Start in Portland and head to the coast (two to three nights), then pop over to I-5 and stop in Eugene (one night) and McMinnville (one to two nights) before ending in Portland (one to two nights).

The details: Even if you’re from the Portland area, it can be fun to spend one night in Portland either at the front or back end of your trip, and a great lodging option downtown is the Society Hotel. From Portland you’ll head straight to the coast where you’ll spend two to three nights. I’d recommend two nights in Cannon Beach (like at this home with major 60’s vibes and a hot tub) and one night camping at the otherworldly Oregon Dunes

From the Dunes, brush the sand off and head east to Eugene for another day and night (we recommend the Graduate Hotel) exploring the city and throwing in a quick hike up Spencer’s Butte for good measure. Next you’re off to wine country where you can spend a night or two in this cozy vineyard cabin as you make your way from winery to winery.

Head back to Portland from McMinnville and don’t forget to bring a case of wine with you.

Option 2: The Mountain Route

The loop: Start in Portland and head east to Hood River (two nights), then down to Mt. Hood (two nights) and finally Bend (two nights) before heading back to Portland. 

The details: From Portland take a short hour-long drive to Hood River where you’ll spend two nights (though you should actually stay across the river at the Society Hotel in Bingen) and two days eating, drinking, hiking, and hopefully getting out on the water. 

After you’ve had your fill of Gorge fun, head south for mountain adventures. If you’re feeling like some fresh air we recommend getting a campsite at Lost Lake, but if you’re longing for a real roof over your head you can splurge on the historic Timberline Lodge. Wherever you stay make sure you get at least one good Mt. Hood hike in. 

From Mt. Hood, you’ll keep driving south to spend two nights in Bend. For a fun stay, look into the Mcmenamins Old St. Francis School (yes, it really was a school) or this cozy cottage just a few blocks from the heart of town. Round out your trip by heading up to Portland, and on your way back hit up Smith Rock State Park and hike Misery Ridge.

With 10 days

This 10 day loop is coast heavy, but the Oregon Coast is so incredible you’ll wish you had 10 more days. 

Pssst! We have an entire guide devoted to planning an amazing Oregon Coast road trip. If you’re looking for more details and coast-specific ideas, definitely read that!

The loop: Starting from Portland again, head west to the coast (three nights), then go all the way down to the Southern Oregon Coast (one night – Samuel H. Boardman is our favorite!). After that, kick over to spend a night in Crater Lake (one night) to see the park at its best when all the crowds are gone, then head north to spend more time in Portland (two days).

The details: We’re adding two nights in Portland at the end of this loop so you won’t see much of the city as you head west for Cannon Beach. Enjoy one night camping at Wright’s For Camping (weird name, I know but the campsites are great and it’s only half a mile into town!). 

Hop on the 101 south and go all the way to Newport with an optional (mandatory) stop at the Tillamook Cheese Factory. Spend at least two nights at the incredible Sylvia Beach Hotel (a book-lover’s dream) in Newport to really explore the area. 

You’ll then pack up and drive all the way down to the bottom of the state and feast your eyes on the breathtaking Samuel H. Boardman scenic area. We’d recommend camping at Harris Beach State Park (and doing all the hikes), but if you want something fancier (read: walls and a door) you’ll have to stay in Brookings or Gold Beach.

Now you’re off to Crater Lake! The route there can feel kinda funky because you’ll actually scoop down into California a bit before cutting north, but the drive on the 199 is gorgeous (and windy) and you can stop for lunch at In ‘n’ Out in Grants Pass before making your final ascent to the lake. There’s lots of camping, cabins, or the fancy Crater Lake Lodge to choose from for accommodation, but you should reserve your spot well in advance. If you can’t swing it, try the Diamond Lake Resort which is fairly close to Crater Lake. 

Round out your trip by heading north back to Portland (and maybe spending a night in Eugene on the way) where you can get your coffee and beer fix. I’ve written a whole guide for a long weekend in Portland if you’re looking for ideas. 

That’s all folks! The perfect road trip through Oregon – an itinerary we hope you want to steal word-for-word!

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