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Portland pretty much has it all: great food and drink, culture and history, and access to the great outdoors without a ton of driving. That’s been great lately since we’ve all been sticking close to home… but if you’re feeling antsy to get away, you might be craving a road trip from Portland – or two.

After living in the Pacific Northwest for four years, I’ve done my fair share of exploring – though I’ll be the first to admit that I still have a ton to see and do in Oregon! Some of the road trips here are ones I’ve done; others are still on my definitely-someday list.

While the Oregon state motto is Alis volat propriis (“She Flies With Her Own Wings”), you can just as easily explore with your own wheels. I’ve put together nine epic road trip itineraries from Portland, giving you the chance to experience the best the Beaver State has to offer – from the coast to the caves, rock formations, and Cascades of Central Oregon. If you’re craving an escape and want to travel safely, consider planning one of these road trips from Portland!


My Definition of a “Road Trip”

Sunset Road Trip

While I write my posts based on experience, I also do a lot of research to back up my suggestions and make sure they’re accurate. I read other articles on the topic to learn what fellow travelers are recommending. But to be honest, as I researched “road trips from Portland,” I found a lot of day trips and destinations. That’s not a road trip!

But here’s the thing: day trips are not the same as road trips and traveling to a destination is not the same as a road trip just because you need a car to get there. There are fabulous day trips and weekend getaways from Portland – but they’re not road trips.

So let’s start with my definition of a road trip: a road trip is a car/vehicle journey that takes you to a series of Points of Interest (POIs) or destinations over at least one night.

The focus of a road trip is as much on the journey (by car) as the destinations themselves. Road trip routes can be one-way, a loop, or an out-and-back (kind of like hiking). While I have recommended one-way road trips in the past (such as my PCH or Southwest road trip itineraries), they include expensive one-way car rentals, so I didn’t include any on this list. Instead, I looked at loop and out-and-back road trips that start in Portland (and end there too).

In this post, you won’t find a list of destinations or day/weekend trip spots you can drive to. Here you’ll only find nine awesome road trip routes from Portland.

What Inspired these Road Trips from Portland

Unlike my other posts like this (which help you plan road trips from Seattle and San Francisco), I’ve actually never lived in Portland. Therefore in addition to my own research, I sought out expert help to come up with these road trip itineraries: Moon Travel Guides’ The Open Road: 50 Best Road Trips in the USA.

This book is seriously so inspiring and helpful if you’re craving a road trip right now – even if you’re not in the Pacific Northwest. There are (as the name suggests) 50 different incredible road trip itineraries to learn about, from the Washington & Oregon Pacific Coast Highways to Monument Valley in Arizona, Door County in Wisconsin (where I visited in August 2020), and a “Best of New England” route that visits some of my favorite places on the East Coast (Newport, Acadia National Park, and Vermont, among others!).

In addition to helping me make sure the recommendations I made for these Portland road trips are spot-on, I’m also inspired to write a post about the best road trips on the West Coast – that one’s coming soon!

Get inspired yourself and pre-order a copy of The Open Road: 50 Best Road Trips in the USA. I’m sure it will be my go-to guide for 2021 which is shaping up to be a big road trip year!

How I Make Road Trip Maps

Like in many of my other road trip posts, I’m using Roadtrippers to make the maps you see in this post. This post isn’t sponsored by Roadtrippers or anything, but gimme a sec to explain why you should use their maps instead of other map tools:

  1. Their name is Roadtrippers. They are obvs experts.
  2. Their map interface is way easier to use when adding POIs and reorganizing them.
  3. They provide the distance and time estimate data between each stop by default.
  4. Every trip has a total estimated time, distance, and gas cost. That last one is freaking gold.

Anyway, you’ll see a map for each Portland road trip below; you can click the name of the trip on the map itself to jump to a bigger view with a lot more detail.

(If you dig these maps and want to make your own, I used Roadtrippers Plus to create this route; you can get $5 off Plus by clicking this link and using code BTR5QTP.)

The 9 Best Road Trips from Portland

1. Mt Hood Circuit

Mt. Hood Circuit on Roadtrippers
  • Suggested Days: 2-3
  • Suggested Overnights: Hood River, Timberline Lodge

If you need a quick road trip getaway, this is the perfect one: it’s close to Portland but far enough to make you feel like you’ve had an escape.

On the first day, you’ll meander up the Columbia River Gorge – stop at leisure to enjoy sights like Vista House and Multnomah Falls before your first night in Hood River. On day 2, make your way around the east side of Mt. Hood and end the day at the iconic Timberline Lodge. You can either stay the night here and explore the volcanic slopes in the morning or drive back to Portland tonight.

2. The Oregon Coast

Portland Trip on Roadtrippers
  • Suggested Days: 4
  • Suggested Overnights: Astoria, Newport, Crescent City

You already know I love the Pacific Coast Highway from top to bottom; I’ve written about it from Seattle to San Diego. While most people primarily focus on California when planning a PCH road trip, I strongly advocate for also driving the Washington and Oregon coasts if you have the time.

The Oregon Coast makes for its own great road trip from Portland too, if you’re based in the Rose City and don’t want to drive the entire Pacific Coast Highway. Set out from Portland to Astoria and work your way southbound (just like I advise for the entire PCH).

In terms of stops, I always recommend Seaside and Haystack Rock, Newport and Devils Punchbowl State Park, and Oregon Dunes National Recreation Area along the coast. As your road trip comes to an end, you’ll actually drop into California briefly for one final overnight in Crescent City before driving back to Portland.

3. Chasing Waterfalls

Chasing Waterfalls on Roadtrippers
  • Suggested Days: 5-6
  • Suggested Overnights: Hood River, Sisters, Chemult, Salem

While there are certainly beautiful waterfalls in the Washington and California Cascades (and Sierras), Oregon seems to take the cake in sheer number of waterfalls and beauty. (Actually, California has about a dozen more waterfalls than Oregon – but think about the two states’ relative size! Oregon is the waterfall capital of the West!)

Okay, now that we agree Oregon is the place to go chasing waterfalls, here’s the perfect road trip to do it. Start by heading east along the Columbia River Valley, where you can stop at a number of falls: Multnomah (obviously!), Latourelle, and Wachella. After an overnight in Hood River, turn south and stop at Ramona Falls before continuing southward toward Bend.

Near Sisters, you can do a loop into the Cascades to see Sahalie Falls and Koosah Falls and Proxy Falls. South of Bend you can take two detours to Tumalo Falls and Dillon Falls, before another overnight in the tiny town of Chemult. From there, head back across the Cascades to Watson Falls and Toketee Falls; Mill Creek Falls is also a worthy detour if you want to spend the time. After a long drive and final overnight in Salem, you can stop at two final falls – Silver Falls and Abiqua – before returning to Portland.

The craziest part? There are hundreds of other falls to see too – if you have the time or extra days, feel free to let your waterfall-chasing explore any trails you find.

4. Central Cascade Volcanoes

Central Cascade Volcanoes on Roadtrippers
  • Suggested Days: 6-7
  • Suggested Overnights: Detroit, Sparks Lake, Paulina Lake, Crater Lake, Lake of the Woods

In my other road trip guides like this one (for Seattle and San Francisco), I had fun putting together road trip routes that explore the volcanoes in the Cascade range that runs through the region. In fact, there’s a dormant/extinct volcano right in Portland (Mt. Tabor)!

In Oregon, my route takes you from Mt. Hood south; you’ll criss-cross the Cascades to visit stops like Mt. Jefferson, The Sisters (three volcanoes!) and nearby Mt. Bachelor, the Newberry Caldera (and cool Devil’s Garden Volcanic Field), and – of courseCrater Lake and neighboring Mt. McLoughlin.

If you, like me, watched Dante’s Peak and Volcano a few too many times as a kid, this is the route for you!

5. Central Oregon’s Caves

Portland Trip on Roadtrippers
  • Suggested Days: 5
  • Suggested Overnights: Sisters, Bend, Fort Rock, Grants Pass

Have you figured out yet that Oregon’s geology is really freaking cool? Okay, let me try and convince you with two more routes (this one and the next).

If waterfalls and volcanoes aren’t your style, how about caves? I also love caves (in addition to waterfalls and volcanoes) and am especially drawn to volcanic cave systems (like Pluto Cave near Mt. Shasta, which I’ve explored a couple of times!). This road trip strings together a bunch of caves formed in different ways: volcanic lava tubes (like Skylight Cave, Lava River Cave, Redmon Caves, and Derrick Cave) and solution/karst caves (Oregon Caves National Monument and Preserve).

As if that’s not enough, you could add a few extra days and head out to see sea caves (Sea Lion Caves), too! (Use the map to turn on that stop if you plan to add it to your trip.)

6. Otherworldly Oregon

Rock Formations of Central Oregon on Roadtrippers
  • Suggested Days: 5-6
  • Suggested Overnights: John Day Fossil Beds, Painted Hills, Smith Rock

While the Cascade Region is certainly stunning in terms of natural beauty, that’s not all Oregon has to offer. If you have less than a week and want a different road trip, consider heading into Central Oregon to explore some of the otherworldly landscapes there. This is a road trip that works best if you’re up for car camping.

The first stop is John Day Fossil Beds National Monument; there are three parts of this park and you can visit two of them: the Sheep Rock Unit and the Painted Hills Unit. Spend your first night in the Painted Hills Unit – and the following day exploring. The following day, head to the rest of the Painted Hills the next day. This area is worth a half-day after spending the night there.

It’s a shorter drive from the Painted Hills to Smith Rock State Park, the final stop on this trip. Here I think you need an extra day too, which is what takes this trip up to the 5-6 day range. You can certainly do it faster (in as short as four days), but I think you’ll feel rushed and like you didn’t see the sights you drove all that way for.

7. Cheese & Wine Route

Oregon Wine & Cheese on Roadtrippers
  • Suggested Days: 2-3
  • Suggested Overnights: McMinnville, Tillamook

This Portland road trip is for the foodies out there – who have somehow never done a multi-day trip to the Willamette Valley! Some of the road trips on this list are well-known and named – others are ones I’ve put together and named myself. This is one of the latter, and I couldn’t help but name it honestly: it’s a road trip to sample Oregon’s best wine and cheese.

The first stop is McMinnville, home to many of Oregon’s best wineries. You can spend the evening of the first day tasting wine – or stretch it to a full day afterward. Then head west to the coast to Tillamook where the cheese of the town’s namesake is made. (If you want to level-up, bring wine from McMinnville to Tillamook and host your own cheese and wine pairing that night!)

This is a delicious and quick road trip from Portland, and probably one you’ve never considered.

8. Oregon’s 7 Wonders

The Seven Wonders of Oregon on Roadtrippers
  • Suggested Days: 9+
  • Suggested Overnights: Astoria, Newport, Crescent City, Crater Lake, Smith Rock, Painted Hills, The Wallowas, Hood River

Did you know that Oregon has its own Seven Wonders? Once you see the list, you’ll agree why it makes sense:

  1. The Oregon Coast
  2. Crater Lake
  3. Smith Rock State Park
  4. The Painted Hills
  5. The Wallowas
  6. Mt. Hood
  7. The Columbia River Gorge

While the road trips from Portland that I’ve shared so far have taken you to each of these places – this itinerary strings it all together. I think you need at least nine days to do it, but you can certainly extend it to have more time in places like Crater Lake, Smith Rock, and the Wallowas…

This is the longest road trip on the list, but if you have the time, it’s an unforgettable tour of the best Oregon has to offer.

9. The Oregon Trail

The Oregon Trail on Roadtrippers
  • Suggested Days: 6+
  • Suggested Overnights: Nyssa, John Day, Madras, Hood River, Cannon Beach

Last – but certainly not least – this is the road trip for us 80s kids! The Oregon Trail is so named because of the route it follows to the Pacific Coast, and you can drive this route for yourself… though not in a covered wagon, and hopefully less dysentery.

Start by making this road trip from Portland to Nyssa, the first Oregon town along the Oregon Trail route. Follow the route – which has signs the whole way – to the town of John Day. On day three, it’s on to Madras; never mind this stretch alone would have taken 2-3 days by wagon! Next it’s north to the Columbia River and the town of Hood River… it must have been reassuring to reach a river that was so near its terminus at the Pacific Ocean. On the final day, follow the Columbia River Gorge to Portland, and then back across land to Cannon Beach where the trail officially ends (you’ll need to return to Portland the following day).

In just six days, you’ve traversed a route that would have taken settlers at least twenty days in the early 19th Century – and with fewer broken axels!

Which of these Portland road trips will you be planning first? Let me know in the comments – and any other questions you have too!


This post was sponsored in part by Moon Travel Guides (Hachette Book Group). I received an advance copy of The Open Road to highlight as part of my road trip planning process.

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