Best of Oregon Road Trip Itinerary: An Unforgettable Adventure!

By Kay S
Last Updated

Welcome to our Oregon Road Trip Planner!

The Oregon Coast Road Trip along Highway 101 is one of our favorite road trips in the world.

This trip along the Pacific Coast has everything from panoramic beaches, fog-shrouded hiking trails, secret coves, quaint beachside towns, artist communities, and even redwood trees!

Yes, those giants are not limited to North California but also thrive in southern Oregon. 

The best place to see them? Along the Oregon Redwood Trail, of course! 

In this itinerary, we have also included attractions further inland which means along with sandy beaches and buffs….

….you also get to see beautiful waterfalls, stunning blue lakes, volcanic domes, hot springs, and desert landscapes..

After all, this is Oregon – Things look different here

Related: Best Places to Visit in Oregon

Oh, and if you love craft beer you are going to love Oregon.

Throughout the state, you can find brewpubs, microbreweries, craft beers served in restaurants, and beer aficionados!

Use this itinerary to plan a stunningly spectacular Oregon Road Trip now! 

What is the best time to visit Oregon?

Oregon is just stunning to visit throughout the year, even in winter and spring.

In winter, you may not see the cornflower blue Crater Lake and will definitely need a car with snow chains but it still looks beautiful.

However, if you want a relaxed trip with no chance of getting stuck in a blizzard, then the summer is your best bet for visiting eastern Oregon. 

In summer, you will find excellent weather throughout the state and wildflowers in the mountains.

Summer is perfect for hiking with the sunset as late as 9 pm in the northern part of the state.

The water is also good for swimming, though in our opinion the Pacific is always too cold to swim! 

Winter and spring are usually rainy/windy for the coast.

If you are visiting in these seasons, we recommend bringing raincoat or rain jackets and an umbrella.

Further inland, you will encounter snow and even blizzards.

Bring along warm jackets and thermals, and get snow chains on your tires.

Also, remember: snow chains may void rental car agreements so skip visiting Crater Lake or any nearby areas in winter if renting a car or read your rental agreement carefully. 

Fall is another good time to visit, especially in early fall.

The Columbia River Gorge region looks spectacular with fall colors and the Willamette Valley wineries have harvest events.

How many days do you need to see Oregon?

Oregon is quite vast – you don’t realize how vast unless you look at the state map!

The I-5 and Highway 101 are quite far from the eastern side.

Thankfully, most major attractions are located along these two roads, making it feasible to see the Best of Oregon in a week or so. 

If you like slow travel, then keep aside 10 days to 2 weeks for this road trip.

On the other hand, if you are short on time then you can easily split your trip and do the coastal attractions in 4 or 5 days, keeping aside the interior for another visit. 

Ultimate Oregon Road Trip Itinerary

This ultimate Oregon Road Trip Itinerary will take you through the best attractions in the state.

We have written this itinerary down along the coast starting in Portland and then up again towards this vibrant city. 

Whether it’s along Highway 1 in California or along Highway 101 in Oregon, we love driving along the Pacific Coast from the north to the south.

That way, the best views are on your right side and it is easy to stop at pullouts. 

Also, Portland makes a great city to fly in and out of, as well as to rent a car.

If you want to drive in the clockwise direction or fly into Eugene or someplace else, you can still use our itinerary – it is really easy to customize as per your interests. 

With that said, let’s dig down into what makes Oregon so special and how to plan a road trip along it all! 

Portland and the vicinity – 3 Days

Portland is a very convenient city to begin your Oregon Road Trip Itinerary.

But before you take the car and hit the Oregon coast, we would recommend spending a few days in Portland to experience its unique culture and vibe.

You should also check out the natural attractions just outside of Portland. 


Portland is pretty unique and known for its hipster culture.

The city goes by the slogan, ‘Keep Portland Weird‘. That should give you some idea of what to expect in this unique, vibrant city.

Bacon doughnuts, eateries serving ethically sourced foods, food trucks, board game cafes, karaoke bars, bike shares, indie coffees, murals – that sorta things! 

The Pacific Northwest’s incessant rains and humid climate provide a great growing environment for the city’s plants, trees, and bushes.

As a result – you will find many beautiful gardens in this city. 

Our favorite is the famous Japanese Garden.

Located within Washington Park, this beautifully landscaped garden is so tranquil that it transports you into a different world. 

Other things to do in Washington Park, Portland’s famous urban park, include the International Rose Test Garden, the Oregon Zoo, Children’s Museum, and more.

Keep aside at least half a day to see this area.

Another essential stop: Powell’s City of Books!

This used bookstore located in the Pearl District is a Portland landmark, akin to NYC’s Strand or Denver’s Tattered Cover Book Store.

Here you will find a million books, book readings and signings, and even writing workshops.

Book lovers can spend hours browsing through the books – if you have one, be prepared to literally drag them out to see the rest of Portland!

Other things to do in Portland include visiting the famous Pittock Mansion, Portland Art Museum, Oregon Museum of Science and Industry, the chic Pearl district, the Lan Su Chinese Garden, and the Hoyt Arboretum.

If you want to focus more on experiencing the city rather than checking out attractions, then we’d suggest exploring more of the Pearl District.

This cool area was formerly a railyard and has the perfect mix of art galleries, cafes, boutiques, craft breweries, and pubs. 

Portland’s food scene is pretty amazing.

The city’s Voodoo doughnuts are popular with tourists but locals recommend Blue Star doughnuts.

Blue Star has plenty of unique flavors; Blueberry Bourbon Basil doughnut anyone?

If you do happen to visit Voodoo, don’t forget to take a photo with the ‘Keep Portland Weird’ sign which is located near the doughnut shop.

Another local chain worth trying is Salt & Straw ice cream.

They have unique flavors and a must for Portland visitors.

Other famous ice cream shops are Fifty Licks and Ruby Jewel.

For exotic cocktails, a visit to the famed Hale Pele Tiki Bar is essential.

Bring along friends and try their famous Volcano Bowl.

For real food (enough with ice creams, doughnuts, and cocktails), try Pok Pok’s fish sauce chicken wings

The city is also famous for its dumplings.

Portland also has many farmer’s markets where you can shop for organic produce and artisan products.

And don’t forget the horde of food trucks pampering every taste bud.

Where most cities have a truck or two lining up the sidewalks, Portland has food truck pods – areas where dozens of carts and trucks are parked next to each other, waiting for your patronage!

Wondering how much time to spend in Portland?

You ideally need at least 2 to 3 days to see most of Portland but you can cover the highlights including the Pearl District and Washington Park in a day if you have less time.

To make the most of your Portland trip, read our post on 29 Epic Things to do in Portland, Oregon.

Fun fact: Feeling lazy? Well, at least you don’t need to get out of the car to fill up on gas!

That’s right, Oregon is the second place where we encountered gas station attendants. The other being New Jersey!

Columbia River Gorge National Scenic Area

The Columbia River Gorge is one of the most beautiful places to visit in Oregon.

While the area is vast, you can easily see it on a day trip from Portland on the Historic Columbia River highway.

Located just half an hour away, the national scenic area is full of trails, waterfalls, scenic drives, and lookout points.

We recommend driving along the 20 mile long Historic Columbia River Scenic Byway to explore the area.

Some of our favorite spots along the highway are Multnomah Falls, Bridal Veil Falls, Latourell Falls, and Vista House.

The parking lots along the byway, especially at Multnomah Falls, get full on weekends, so we recommend arriving early in the day. 

The #1 tourist attraction in the Columbia River Gorge area is the Multnomah Falls.

At 620 feet, the waterfall is the tallest of the many waterfalls in the gorge.

This beautiful waterfall has two drops, creating the upper falls and lower falls.

The picturesque Benson Bridge creates a perfect place to view the falls.

While you can see the falls from below after a 5 mins walk from the parking lot, you need to scramble up to Benson Bridge and another mile to reach the viewpoint at the top.

Another must visit is the Multnomah Falls Lodge which has a visitor center and is a designated historic place. 

Other things to do in the gorge region include hiking, boat cruises, visiting dams, winery tasting, waterfall hiking, etc.

We would recommend seeing Portland and the Columbia River Gorge area before beginning your Oregon road trip in either clockwise or counterclockwise direction as per your interest. 

The rugged Oregon Coast Road Trip – 3 Days

Oregon Coast is a different beast compared to most of the Californian Coast.

It is windy, rugged, wet, foggy, and cold. It is also beautiful and dramatic. 

Along the coast, you will find gorgeous geological formations including Haystack Rock, Thor’s Well, sand dunes, etc.

You will also find rainforests, artsy communities and beachy towns – plus, lots of seafood! 

The route you’ll be following – Highway 101 – completely parallels the coast and is a pleasure to drive. 


We recommend starting your coastal road trip in Astoria in the north.

This pretty coastal town has many things to offer.

Start your visit by climbing to the top of the famed Astoria Column, a historic tower with stunning 360 degree views of Astoria and the coast. 

Other things to do in Astoria include:

the Columbia River Maritime Museum which narrates the seafaring history of the area,

the Lewis and Clark National Historical Park which is home to the historic Fort Clatsop,

and the Fort Stevens State Park where you can see a historic shipwreck. 


Next stop at the resort town of Seaside.

It’s main attraction is the Seaside Promenade, a 1.5 mile long boardwalk, which is perfect for a stroll.

Other things to do include spotting harbor seals at the Seaside Aquarium, exploring the art galleries in town, sampling some of the famous Sea Star Gelato. 

While you are in Seaside, stop by the Bell Buoy, a locally owned seafood market where you can also order specialties like fish and chips, clam chowder, crab melt, and oyster shooters.

This is also a great place to pick up something for a picnic lunch. 

Cannon Beach

After leaving Seaside, head for the Cannon Beach area. Walk on the beach and marvel at the sea stacks.

To take the most photographed view of Haystack Rock with Cannon Beach in the background, visit Ecola State Park

From here, you can also spot the Tillamook Rock Lighthouse.

The state park is also good for wildlife watching including bald eagles, brown pelicans, tufted puffins, elk, seals, sea lions, and migrating gray whales.

The park also has tidepools where you can spot a variety of low tide creatures. 

Rockaway Beach

Rockaway Beach is a charming Oregon coastal town and has been a popular West Coast beach getaway for families since many years.

A highlight is the Twin Rock formation off the coast.

In the town, you will find charming buildings, shopping, and seafood restaurants.  

Tillamook Coast

For a change of pace, ride the Oregon Scenic Coast Railroad between Rockaway Beach and Garibaldi.

This historic train will take you along the coast and has many special excursions in the Tillamook Bay area. 

Then stop at the famous Tillamook Creamery.

The Creamery / Cheese factory is an essential stop on the Oregon coast road trip.

At the factory, you can go on a self- guided tour of the cheese making and packaging process.

You can sample a few cheeses as well as buy some for the road – plus, they have ice cream!

This stop is a favorite with families and kids. 

Post Tillamook, you can either follow Highway 101 inland or take a detour towards the Three Capes Scenic Drive.

Along this scenic road, you will have amazing views of Cape Meares, Cape Lookout, and Cape Kiwanda.

This road is a hidden gem and was a highlight of our road trip. 

Cape Perpetua

Next visit Devil’s Punchbowl and the Yaquina Head Lighthouse, before driving to Cape Perpetua Scenic Area.

See the view from Cape Perpetua Lookout point, visit Thor’s Well, see the spouting horn which shoots water into the air, and see the Devil’s Churn.

Next stop at the famous Heceta Head Lighthouse.

The lighthouse position is extremely scenic and makes for iconic photographs.

You can also tour the lighthouse, see timings on the official website. 

Other stops as you make your way south include the Oregon Dunes, Coos Bay, the state parks near Bandon beach, and the Samuel H. Boardman Scenic Corridor.

The views along the corridor are especially scenic and we fell in love with this scenic road trip. 

The total distance from Astoria in the north to Brooking in the south is about 8 hours (~340 miles).

We recommend breaking it into ideally 3 to 4 days so you can hike, take scenic drives, enjoy time at the beach, visit local restaurants and factories, explore museums and antique stores, and generally, have a grand time. 

If you have only two days to see the coast, we would recommend visiting our favorite attractions of Cannon Beach, Three Capes Scenic Drive, Cape Perpetua Scenic Area, and the Samuel H. Boardman Scenic Byway. 

If you can hike only one trail, hike to Thor’s Well. If you can visit only one lighthouse, visit the Heceta Head Lighthouse.

Don’t forget to visit Tillamook Creamery and eat the seafood at Bell Buoy.

Stay the night at either Newport or Florence near the Heceta Head Lighthouse and observe the stunning sunsets on the Pacific. 

If you have more time, then plan a leisurely drive down to Southern Oregon coast.

There is so much more to see and do on the Oregon coast beyond the attractions mentioned in this itinerary. 

You can see unique sites like the Goonies filming location in Astoria, Indian beach, Cape Meares Lighthouse, check out breweries along the coast, stroll along the Garibaldi Pier, go whale watching, visit the Oregon Aquarium at Newport, explore the Old Town of Florence, etc. 

To find out our 25 favorite stops along the Oregon Coast and plan your road trip along Highway 101, read our separate post on Ultimate Oregon Coast Road Trip Itinerary

Through the Cascades – 2 Days

In central Oregon, you will find the beautifully breathtaking Cascade Mountain ranges – a must stop on any Oregon Itinerary.

This region of Oregon is stunning with snow capped mountain ranges, amazing hikes, a variety of outdoor adventures, and charming mountain towns. 

That’s why, we recommend adding Central Oregon to your Oregon state road trip.

Those who come to see only Portland and Coastal Oregon are missing out on the diversity that the Beaver State offers to its visitors. 

Here you will find majestic mountain peaks, dense evergreen forests, beautiful mountain lakes, skiing in winter, and lots of wildlife encounters. 

Where you start your Cascades part of the trip depends on how far south you go along the Coast.

If you go down to Brookings, you will need to enter California before you can reach Central Oregon. 

Irrespective of that, your first stop should be Crater Lake National Monument. 

Crater Lake National Park

No road trip in Oregon is complete without visiting Crater Lake National Park.

This is a majestic place to visit year round though in the winter, you will be treated to closed roads and snow on the rim.

The lake itself always looks a mysterious and shimmering blue. 

There are many ways in which you can enjoy the astounding scenery of this beautiful place.

Drive the scenic rim drive or go hiking into the surrounding forest.

Stop at the pullouts and take stunning photographs of Crater Lake.

In the summer, you can also swim in the lake at Cleetwood Cove. 

This deepest lake in the country was formed when the Mount Mazama volcano erupted more than seven thousand years ago and water filled up it’s collapsed caldera.

You can read more about the fascinating history of this geological wonder at the visitor center. 

Optional: Umpqua National Forest

The Umpqua National Forest is a gorgeous region to add to your road trip through Oregon.

While the recent wildfires in Oregon have affected the outdoor recreation area, it still remains quite beautiful.

You can go on scenic drives through the mountains or enjoy hiking trails.

There are also many waterfalls and swimming holes in the forest where you can go hiking, fishing, and swimming. 


Located on the banks of the Deschutes River on the eastern slopes of the Cascade mountains, Bend is a delightful and charming city.

In the city, you will find boutique shopping, craft breweries, coffee shops, and trendy eateries.

Talking of breweries, Bend is famous for its beer scene and even has an ale trail – it is a must for beer lovers! 

Bend is also famous for its plenty of outdoor recreation opportunities.

In summer you can enjoy watersports and go on hiking trails while in the winter, you can go skiing, snowshoeing, and snowboarding.

This is really a fantastic city to visit while in Oregon. 

Cascade Lakes National Scenic Byway

Cascade Lakes National Scenic Byway begins in Bend and is an amazing drive to enjoy the stunning summer scenery in the Cascades ranges.

The drive is 66 miles long and takes about half a day to complete considering the stops.

The route goes through the Deschutes National Forest, Three Sisters Wilderness Area, and beautiful mountain lakes. 

Optional: Deschutes River

If you have time and are looking for a relaxing and cooling day in the summer, then consider a floating trip down the Deschutes River.

This river in central Oregon is perfect for river tubing.

You can rent floats, kayaks, or canoes in Bend and can launch your trip from the Riverbend Park.

You can also try whitewater rafting along the river or go fishing.

The river is a must on your Oregon road trip itinerary for water lovers. 

After visiting Deschutes River, you can drive northwest towards Oregon.

However, if you have the time we would suggest exploring the beautiful bare, rugged landscape of eastern Oregon. 

Optional: Via the desert landscapes of Eastern Oregon – 2 Days

While Eastern Oregon has many unique desert landscapes including:

the Painted Hills, Owyhee Canyonlands, Hart Mountains, and Alvord Desert,

We recommend visiting just the Painted Hills and other units of John Day if you have less time. 

John Day Fossil Beds National Monument

John Day Fossil Beds National Monument in Oregon is located close to Deschutes River.

The monument comprises 3 units: Painted Hills, Sheep Rock, and Clarno. 

Painted Hills is the most visited unit of the National Monument. 

The monument is most renowned for the excellently preserved fossils of plants and animals that lived in Eastern Oregon millions of years ago.

The fossils span over 50 million years and this is one of the most complete fossil records in the world. 

The monument and it’s units are located in rural Oregon.

Here you will find tiny villages, open ranches where cattle wander onto the roads, and very basic amenities.

We suggest filling up on gas whenever you encounter a gas station, you definitely don’t want to be stuck in these parts! 

Painted Hills

Painted Hills is a beautiful, magical landscape that looks even more stunning at dusk or dawn.

It looks even more vibrant after a rainfall when the colors on the hills are vivid and alive.

The site is considered among the Seven Wonders of Oregon and is a must visit while in the state. 

There are many things to do in the Painted Hills unit of John Day and several ways to take in the beauty of the area.

Hike to the iconic Painted Hills Overlook to get a panoramic view of the colorful hills.

Hike the short Painted Cove Trail to get up close to the hills or hike the 1.6 mile round trip Carroll Rim Trail to see the sweeping vistas. 

Optional: Owyhee Canyonlands

Southeastern Oregon’s Owyhee Canyonlands seems to belong more to the American Southwest than to the Pacific Northwest.

Here you will find a red rock landscape reminiscent of Sedona and spectacular, eroded canyons. 

Not many visitors come here, keeping this one of the best kept secrets of Oregon.

This volcanic landscape has been carved by flowing rivers and glaciers and contains several badlands, clifftops, canyons, and desert landscapes. 

One of the best ways to explore this remote attraction is by hiking.

Take to the trails and discover beautiful spots such as Leslie Gulch, Jordan Craters, and Painted Canyon Loop.

Remember to bring maps, plenty of water, and other hiking essentials as there are no amenities near the Canyonlands.

Also, you will need a 4WD vehicle to make the drive out here as it is on unpaved roads.

Optional: Alvord Desert

Alvord Desert is located in southeastern Oregon near the Steens mountains.

This was once a lake that was several hundred feet deep.

Today, you will find just a dry lake bed and a beautiful desert landscape.

The minerals from the lake are deposited over hexagonal cracks in the ground.

In some ways, Alvord Desert is similar to Death Valley.

It is also eerily silent and one of the most underrated destinations in Oregon. 

The area is famous for its geothermal activity and it is said that at night, you can hear booming noises from the seismic activity.

Visitors often camp here in this desolate landscape because of its unprecedented beauty plus the camping here is free and doesn’t need any permits.

That’s right, you could just walk up here, set up your tent, and enjoy the sunset before you turn in for the night. 

On the western edge of the Alvord Desert, you will find the Alvord Hot Springs.

These are a result of the high seismic activity in the area.

They are privately owned and can be accessed for a small entry fee.

Here you will find two simple concrete pools with wooden edges to sit.

If you camp here, you can soak in the hot springs even at night.

This is a truly one of a kind outdoor experience in Oregon. 

While you are there you can also drive the Steens Mountains Loop drive which is 60 miles long and takes about 2 hours.

The views along the drive are beautiful and there are lookout points at regular intervals.

Other useful posts to plan your Pacific Coast Highway Road Trip

Pacific Coast Highway Road Trip Planner
Pacific Coast Highway 4 day Itinerary
Pacific Coast Highway 5 day itinerary
Pacific Coast Highway 7 day itinerary
Pacific Coast Highway 10 Day itinerary
All PCH Itineraries
Best Places to Stay along the Pacific Coast Highway
Best Pacific Coast Highway Stops

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