An Oregon Road Trip Itinerary for Seven Incredible Days

Our road trip through Oregon will go down in history — I mean, my personal history — as one of my favorite road trips of all time.

We enjoyed it enough that if we weren’t already living in California at the time of that trip, we might have considered Oregon a contender for something more long-term.

We’ve returned numerous times since for deeper dives into the Beaver State’s rugged coasts, delicious wines, and outdoor pursuits. We’re still not done with Oregon and the Pacific Northwest.

Spend as much time as you’re able, but this is our own Oregon road trip itinerary to the best of the state in just one week.

Is Oregon worth visiting?

Oregon is worth visiting for its diverse landscapes, quirky charm, and delicious cities that offer a farm-fresh scene sure to delight the most discerning foodies.

I’m not that picky, by the way. Oregon is just next-level when it comes to its dining, especially if you visit the Willamette Valley.

Oregon is the ideal escape for outdoor adventurers, too. This is a year-round state for hiking, biking, and even skiing if you’re not afraid of the slopes as I am. There’s something here for any kind of traveler.

How Much Time You Need in Oregon

How many days you should dedicate to an Oregon trip depends on what you’d like to see. You could get away with a long weekend in Portland that includes a day trip out to the coast. A full week will give you the chance to see more of the state’s diversity.

How to Plan the Best Road Trip in Oregon

To plan a successful trip, always plan ahead. Oregon isn’t some unknown destination in the United States by any means. Book accommodations well ahead of your trip, and nab that rental car as soon as you have flights. Oregon road trips are popular for a reason.

As far as when you should go, seasonal weather won’t affect much of this itinerary. If you’re sold on seeing Crater Lake — and you should be! — you’ll have the most fun in July or August.

The trails won’t be snowy, all of the roads around the lake will be open, and you’ll have access to the boat tours at that time. The park doesn’t get too busy in the peak summer season, either, as it’s pretty difficult to get to.

Summer into early fall is your best chance at sunny skies for an Oregon coast trip, too. Things can get pretty blustery there regardless, so pack accordingly.

My Seven-Day Oregon Road Trip Itinerary

An efficient week on the road in Oregon looks like this:

• Day 1: Portland
• Day 2: The Oregon Coast
• Day 3: The Willamette Valley
• Day 4: The Columbia River Gorge and Mount Hood
• Day 5: Crater Lake National Park
• Day 6: Bend
• Day 7: Portland

This itinerary assumes your arrival in Portland, the state’s main transportation hub, on the first day.

Whether you’re arriving in the morning, well into the afternoon, or in the evening, make the best of your time in this quirky city.

Note: My Day 1 here is then technically your Day 2. It’s a full day’s worth of activities in Portland and where the itinerary will begin.

If you have a decent amount of time the previous day, try to get to what you consider to be must-sees for yourself in Portland, eating some good food along the way. At the very least, get a good night’s rest for the active week ahead.

Oregon Road Trip Day 1: Portland

I have a guide for you to the perfect day in Portland, but here are some highlights:

• Satiate your sweet tooth. Embrace your inner weird and head over to Voodoo Doughnut, where “the magic is in the hole.” That’s their slogan, not mine.
• Smell the roses at Washington Park. This is where you’ll find the International Rose Test Garden. One of Portland’s nicknames is “The City of Roses,” so you know this one’s got the goods.
• Browse the shelves at Powell’s Books. This is the largest independent new and used bookstore in the world and a landmark in Portland.
• Try the city’s food trucks. Nong’s Khao Man Gai is my favorite. If you want to try it out, head over to the Ankeny Square Food Trucks for the city’s must-eat chicken shop.
• Walk it all off at Tom McCall Waterfront Park. The 36 acres of this popular green space are perfect for strolling and relaxing. It’s all kinds of loveliness.

We stayed overnight at the Tiny House Hotel. While it has since become another pandemic casualty, I’d recommend you take advantage of the city’s quirkiness for accommodations that are a bit more unique.

Use the map below to browse your options in Portland:

Oregon Road Trip Day 2: The Oregon Coast

Start off the day with a coffee or return to Voodoo Doughnut if you’re feeling extra indulgent. Today you’re hitting the road and driving the Oregon coast.

If you only have one day to explore, I’ve put together some highlights below with easy access from Portland. Here are a few of my favorite coastal towns in Oregon:

• Astoria: This fishing town looks cute, but it’s also known for being the “Graveyard of the Pacific” thanks to the treacherous waters that surround it. See evidence of that at the nearby Fort Stevens State Park, home to the Peter Iredale Shipwreck.
• Cannon Beach: If you head to the Oregon coast and don’t see Haystack Rock, also affectionately known as “Goonies Rock,” did you even go to the coast? It’s basically a right of passage. Check out views from above, too, at Ecola State Park.
• Manzanita: This is ideal Oregon beach time without the crowds. Manzanita offers up access points to hike up Neahkahnie Mountain and the nearby Hug Point State Recreation Site. It’s the perfect place for a picnic if it’s time to pull over.
• Oceanside: This was my favorite stop on our Oregon coastal tour, perhaps because there was nothing there to do but listen to those waves crashing onto the shore. This is the state’s remoteness at its finest.
• Tillamook: Tillamook is a short drive inland from the coast and the magical Cape Kiwanda State Natural Area, but I have to include it here because of one thing: cheese. Visit the Tillamook Creamery and tell me I’m wrong.

READ MORE: There’s more where that came from. Check out my guide to the best Oregon coastal towns.

If you have more time, lucky you! Explore more of the southern Oregon coast near the Samuel H. Boardman State Scenic Corridor or ride the dunes at the Oregon Dunes National Recreation Area. You can also make your travel in Oregon a bit more leisurely.

We stayed overnight in Oceanside at Turtlejanes Bed & Breakfast, but you really can’t go wrong with coastal accommodations.

Use the map below to browse your options in and around Astoria, a popular stop along the coast:

Oregon Road Trip Day 3: The Willamette Valley

If you’re into some easy-drinking pinot noir then you’re in the right place.

The Willamette Valley is it for pinot enthusiasts. They have other wine varietals, of course, but pinot is what you’ll feel best sipping on as you enjoy the spectacular vineyard views and share some of your wine knowledge.

I have a guide to the best of Oregon wine country for you to peruse, but here are some wineries you shouldn’t miss:

• Argyle Winery: I will admit Argyle Winery in Dundee was on my list because of the ghost stories and their aptly named Spirithouse Pinot Noir. It turns out they also have an excellent sparkling wine selection.
• Domaine Drouhin: Domaine Drouhin boasts that they have “French soul, Oregon soil,” which was enough to sell me on a visit here. That, and the lengthy pedigree of the winemakers in this family is also impressive.
• Eyrie Vineyards: Eyrie Vineyards is consistently ranked as one of the best wineries in the Willamette Valley. They started with pinot gris rather than the ever-eponymous pinot noir back in 1965.

We chose to stay at the Comfort Inn in Troutdale for easy access to the Columbia River Gorge the following day. It was comfortable enough if you’re looking for a budget-friendly stay.

If you’d prefer to stay closer to wine country, return to my Oregon wine country guide for accommodation recommendations or browse the map below:

With more time, the valley is also a gateway to all kinds of adventure. The Willamette National Forest is an easy enough drive from the wineries featured here.

Oregon Road Trip Day 4: The Columbia River Gorge and Mount Hood

You’ll be continuing your drive inland today to see more of what makes this state so diverse when it comes to its landscapes.

Prepare to be awed by the Columbia River Gorge waterfalls and Mount Hood, which sneaks its way into the most epic Oregon vista photographs.

Stop 1: Vista House

Start out at the Vista House at Crown Point. There’s a museum here, the expected gift shop, and a small coffee stand. Its claim to fame is the views you’ll get here of the Columbia River Gorge, just a stone’s throw away.

This stop has been astounding visitors since 1917, and while it was essentially built for tourists, it’s well worth your time.

Stop 2: Multnomah Falls

Continue driving east and make any stops you’d like that strike your fancy. As I’m replicating our trip here, we drove until the pull-off for Multnomah Falls.

It’s a short walk from the parking area to a viewpoint of the falls, but if you want to stretch your legs, there’s a paved trail to get to Benson Bridge.

From there, you’ll have a view of the top and second tier of the falls. We continued on from here to a viewing area at the top, and the spur trail from there to the tippy top. It was all worth it.

The roundtrip to see all of that is 2.4 miles, which should work up a little bit of an appetite for lunch.

Stop 3: Lunch in Hood River

If you’re as hungry as we were before continuing along the Historic Columbia River Highway to our favorite Mount Hood viewpoints, fuel up at Full Sail Brewing Company.

The brewery in Hood River has beer recommendations for every item on their menu, which is always fun if a bit dangerous at times. I’m a sucker for beer cheese soup, and their version is delicious. Try it with their amber ale.

Hood River is big for windsurfers, so if you’re into that at all, you may want to plan to spend more time here. Otherwise, you can observe them doing their thing from the brewery. That’s as far as I go with traditional surfing back in California, too.

If you’re doing well on time, stop at the Rowena Crest viewpoint for one more look at the Columbia River. This spot is particularly pretty when the spring wildflowers are popping.

Stop 4: Timberline Lodge

You’re fueled up, and ideally, your car’s also fueled up for the drive down to Bend. We took the scenic route to get up close and personal with Mount Hood at a couple of different spots. It’s something I’d highly recommend if you have the time.

The Timberline Lodge and Ski Area was our first stop, about an hour’s drive from Hood River. We had ourselves a snowball fight, which was all kinds of fun, and something that you can do, too.

Fun fact: They have snow there even through the summer months. That’s when we were there, by the way, so I can confirm this is true.

Stop 5: Trillium Lake

The views from Trillium Lake, another half hour south of Timberline Lodge, were an entirely different experience. This is where you’re able to get those mirror image shots off of the lake.

It’s amazing, and, in my humble opinion, the best views of Mount Hood.

Stop 6: Bend

It’s another two hours to Bend from here. That’s where we spent the night. Keep that in mind as you sit in silence and awe at Trillium Lake.

We kept things casual with a stay at the Hampton Inn & Suites Bend, but if you’re looking for something fancier, the Pine Ridge Inn is on my wish list.

Use the map below for more options in Bend:

Oregon Road Trip Day 5: Crater Lake National Park

It’s a haul to get to Oregon’s only national park, Crater Lake, from many major cities in Oregon. That’s why it’s so well-suited for a road trip through the state.

The lake is about two hours away from Bend, which made it a no-brainer day trip for us. A day at Crater Lake is plenty of time for you to take a boat tour around the lake, hike a few trails, and conquer the Rim Drive.

You’ll even have time to take a dip if you’re brave.

READ MORE: Help me plan your day in Crater Lake with my detailed one-day itinerary to the park.

For those with more time, the Crater Lake Lodge or the Cabins at Mazama Village are the only options for accommodations in and around the park. Otherwise, return to your Bend accommodations for your overnight.

Oregon Road Trip Day 6: Bend

If you’ve been following along, you likely haven’t seen much of Bend proper. Its proximity to so many natural wonders is its downfall, but the city’s pretty great all on its own.

Spend a day exploring at your leisure and recuperating from all of the amazing places you’ve been on your Oregon road trip.

If you want to continue seeing all of the things, I have some highlights for you.

Stop 1: Breakfast

Fuel up before you head out with a delicious breakfast or brunch in Bend.

I don’t know what the difference is between the two. Is it timing? Like, if you sleep in, it’s brunch?

In any case, The Lemon Tree is hot on the downtown Bend scene, serving up fancy eggs Benedict and shakshuka. If you’re not sure what that is, we’re talking poached eggs in a tomato sauce that’s so much more complex than it sounds.

If you’re looking for something more homey, head over to the McKay Cottage Restaurant, which operates out of a 1916 craftsman. Indulge in some biscuits and gravy or some stuffed French toast. You deserve it.

Stop 2: Pilot Butte

Pilot Butte, an ancient cinder cone, lies within the city limits. Yes, Bend has a dormant volcano that rises 500 feet above the city.

You can drive all the way up to the Pilot Butte Scenic Viewpoint. I hear a sunset up here is pretty spectacular and gives the mountains quite a glow. There are several trails that start from here, or just enjoy the view.

Alternative Stop 2: Newberry National Volcanic Monument

If you want more hiking options, the Newberry National Volcanic Monument is less than a half-hour south of Pilot Butte.

Note: You could fill a full day here exploring the 54,000 acres of lakes and lava flows, but if you’re short on time, choose one of the three sections in the region: Lava Lands, Lava Cast, or the Newberry Caldera area.

A highlight in the Lava Lands area is Lava Butte, accessible via shuttle, your car when the shuttle isn’t running, or on foot if you want to climb the 500 feet up. From there, you’ll get beautiful panoramas of the Cascades.

Lava Cast features accessible hiking opportunities through lava flows that took over the forests in this area thousands of years ago. The Lava Cast Forest Trail takes you through an easy interpretive trail allowing you to learn some while you stroll.

Fun fact: The Newberry Caldera Area is the farthest area from civilization and is best explored if you have more than a few hours to hit the region.

Once you’re there, access trails at all skill levels that will take you to the beautiful lakes in this part of central Oregon.

Start with the Paulina Falls Trail, an easy stroll — it’s only half a mile roundtrip — to a lovely waterfall.

Stop 3: The Old Mill District and Lunch

Do some window shopping or actual shopping if you’re feeling spendy in this outdoor retail mall, named as such because the shops operate out of old mill buildings.

There are plenty of options here to kick back and have a snack or lunch, too. The Italian bistro Pastini is a great option for carb-loading and patio seating.

Stop 4: Drake Park

Walk off some of that lunch at Drake Park, 13 acres of loveliness along the Deschutes River.

This is where I turned to Brian and was all, “Well, I could certainly live here, especially in that giant riverfront house over there!”

The water feature you’ll pass is Mirror Pond, named as such because of that lovely reflective effect clean bodies of water offer up. You won’t get that at the Chicago River.

Stop 5: Bend Breweries

Bend is the big time when it comes to craft beer. From what I recall, we thoroughly enjoyed the brewery scene in Bend, a beer-lover’s paradise.

I’ll share the highlights, all of which include food if you’re in need of more sustenance at some point as the evening drags on.

One of our favorites was the Crux Fermentation Project, housed in a former transmission repair plant.

Pay attention to your maps app as you drive here, as you’ll have to ignore some “no outlet” signage on your way in. Once you’re there, enjoy their tap list of 20+ brews and a menu of bites and sandwiches.

If you’d like a beer with a view later in the day, their Sundowner Hour in the half hour before and after sunset daily. It’s not only a good deal in terms of their beer specials, but a great way to catch a sunset like no other.

10 Barrel Brewing Co. also serves some yummy grub and non-beer options. That means things like hard seltzer and hard cider. It’s all great.

If you’re feeling like supporting tradition, Deschutes Brewery, a standby in downtown Bend, is always worth a stop. This should be your pick if you’re looking for pizza, as they have a selection of unique pies on the menu.

Ideally, you’re staying in Bend for your overnight after your brewery crawl, and not heading back home until the next morning.

Oregon Road Trip Day 7: Return to Portland

We continued onward through eastern Oregon to start a road trip into Wyoming, Idaho, and Montana from here. We were on a trek to see some of the country’s best national parks on that trip, so our trip didn’t end in Oregon.

If you’re only here for the week, you’ll likely need to return to Portland at some point for your flight back home. Leave about three-and-a-half hours to do so from Bend.

For those with an evening flight, you can spend your morning at nearby Smith Rock State Park. The place is a haven for climbers, but you don’t need to do all that if you just want to hike.

The Rim Rock Trail is just 1.4 miles out and back as an easy introduction to the park and unobstructed views of Smith Rock.

If you want to travel through Salem on this leg instead of the way you came already, you’ll pass near Silver Falls State Park. This is the largest state park in Oregon and home to 177-foot South Falls and the incredible Trail of Ten Falls.

It all depends on what you have time for as you plan your route home.

With More Time in Oregon

If we had more time in Oregon, we would have ticked off any number of Oregon sites that remain on our to-do list. Here are a few:

• John Day Fossil Beds National Monument: See over 40 million years of plant and animal revolution at this Oregon monument in the form of geological formations and fossils.
• Oswald West State Park: This is a coastal destination we missed known for Short Sand Beach. Nicknamed “Shorty’s” by the locals, it’s a popular spot for surfing, but you can also come to lounge if you’re not in to that.
• Painted Hills: These are actually a unit of the John Day Fossil Beds, but they’re worth a shouthout of their own. The colors you’ll see here are the result of millions of years of geological history.
• Tamolitch Falls (Blue Pool): This lovely spot in the Willamette National Forest requires a four-mile roundtrip hike, but the result is a waterfall cascading into a torquoise pool of water. I’m in.
• Umpqua National Forest: Explore the Umpqua River Scenic Byway for a variety of outdoor activities that include hiking, fishing, and wildlife-spotting. It’s also a hub for hot springs if you want a more relaxed approach.

You’ll want to come back to Oregon.

No matter how much time you give this state, you’ll want to plan a return trip as soon as you’re back home. Heck, you may even be doing some plotting on your drive back to the airport.

We’ve been a number of times now and know we’ll be back for more epic road trips, especially to tick off some of the state’s longer hikes. Oregon is a stunner.

Planning more travel in the region? Check these out next:

• Death Valley National Park: Top Hikes and Sites
• A Hiking Guide to Zion National Park
• How Hard is the Narrows Hike? Read This
• Why You Need to See Reno, Nevada
• A Road Trip Along the Extraterrestrial Highway

Visiting California while you’re at it? Read these guides:

• Visit Ramona for Adorable Goat Yoga
• Love Beer? Check Out San Diego’s Best
• How to Plan the Best California Vacation
• Sonoma on the Cheap: Make it Happen!
• A Guide to Visiting Santa Barbara, California

Want to see more?