How to Plan an Incredible Oregon Road Trip (14 Days)

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How Many Days Do You Need for this Road Trip?

First of all, Oregon is a lot bigger than you probably think. It’s the 9th largest state in the country by square mileage, which is a fact that blew my mind. Driving between places can take several hours, if not more. 

Why do we bring this up? Because it has one major implication for your trip.

Unless you want to spend full days of your trip driving without stopping to see the scenery, you’re not going to be able to see the entire state. 

Fear not – we have a strong perspective on where you should focus your time if it’s your first trip to Oregon.

We really, really think that to do a full road trip around Oregon that includes both the northern coast and Bend, you need a full two weeks (14 days). Otherwise, you’ll spend way too much time driving, and not enough time out exploring. 

Which is exactly how we’ve written the road trip below. As you’ll notice when you get there, the two week road trip we’re about to dive into features roughly a week on the east side of the Cascades, and roughly a week on the west side of the Cascades. 

The Cascades are the mountain range that run down the middle of the state, separating the temperate, western third of the state from the drier high desert in the eastern part of Oregon. 

If you have anything less than two weeks, we’d strongly recommend limiting your trip to either the mountains or the coast (perhaps with a day trip or two from Portland to explore them briefly). And we’d DEFINITELY cut the day trip to Crater Lake, because it’s a lot of driving to get there from Bend. 

If you have 7-10 days, we’d do a more focused road trip that follows a figure-8 with Portland at the center. Head east to the Columbia River Gorge, Hood River, and Mount Hood, then come back through Portland and head out to the Oregon Coast for a few nights, focusing on the stretch from Astoria to Tillamook. Here’s a map.

Alternatively, you could spend a week either on the Portland / Hood River / Bend portion of the loop, or spend a week on the Oregon Coast portion of the loop. 

If you do have less time, we have example itineraries for 7 and 10 day road trips below the main itinerary to help you organize your time. 

The Best Time to Do this Road Trip

This is a very, very important section in this guide, which is why it’s one of the first things we’re talking about. 

If you are interested in hiking in the Cascades – specifically near Mount Hood or Bend – your trip will need to be sometime between July and mid-October. 

Otherwise, high elevation hiking trails will be covered in snow, and some roads and trails will be closed. 

The exact timing depends on the year, precipitation, and spring temperatures (among other factors), but you will be most safe with a trip in August or September. That’s when roads are open, trails are largely snow-free, and you’ll be able to see everything you want to see.

During the summer and early fall, mountain passes and hiking trails are clear of snow, days are warm and sunny, the sun rises before 6:00 am and sets after 9:30 pm, and it’s an all around spectacular time to be in Oregon. 

The downside is that, in recent years, Oregon has been ravaged by forest fires during the summer, bringing a thick smoke that makes it really unhealthy and unpleasant to be outside. It’s hard to predict, but it’s something to be aware of if you’re planning a trip in the summer. 

Early fall is another great time to visit Oregon. The weather is, for the most part, still great (though it’s a little more unpredictable than summer). Unfortunately, there is still a chance of encountering wildfires in the fall.

In the spring, hiking trails at elevation – like around Mount Hood and Bend – are still going to be closed. If you’re into hiking, we’d definitely recommend waiting until later in the summer.  

If you’re visiting in the winter, we’d stick to the areas west of the mountains and do the Columbia River Gorge, Hood River, Silver Falls State Park, and the Oregon Coast. For what it’s worth, we’ve done the Oregon Coast multiple times in the winter, and it’s very moody (and wet). 

Here’s a map of what a winter road trip in Oregon might look like. 

Where to Start and End Your Road Trip

This one is easy – Portland! 

Portland is not really central in terms of the state – it’s up in the northwest corner – but it is central to some of Oregon’s best sights (the coast, Mount Hood, the Columbia River Gorge, etc etc) AND it has the best airport in the state (dare we say country?). 

Unless you live somewhere in Oregon or you’re driving from a neighboring state, the answer is Portland. 

The best option, with the most flights coming in and going out, is going to be our home airport – Portland International Airport (PDX). 

The exception is if you have 10 days in Oregon and follow our road trip itinerary below. In that scenario, we’d recommend flying into Portland, and out of Bend (Redmond Municipal Airport, RDM) to save time on driving back to Portland just to catch a flight. 

Flights out of Bend will be more expensive and involve connecting through Portland or Seattle, but it’ll save you four (ish) hours of driving. 

One thing we were interested in prior to acquiring a van of our own is renting an Escape Campervan.

If you’re looking to experience the whole camping thing, but don’t want to sleep in a tent (to be clear, we’re all for tent camping), then a campervan might be for you!

Escape’s vans are all hand-painted, have full kitchens, and would be a lovely way to experience Oregon.

Escape has an office in Portland, which is where you’d pick up and drop off your van. 

Which is basically everything we love about Oregon, packed into two weeks (minus some of the further out spots that don’t make sense here). 

Like we said, you can’t fit it all into one road trip. But we’ve done our best to include the highlights in hopes that you’ll fall in love with Oregon and come back a second (and third) time to explore more. 

Of course, that’s just the base itinerary that we’d recommend. The exact route you take is going to depend on your particular interests, what time of year you’re visiting, and more factors than we can possibly take into account here. 

We have ideas for shorter and longer itineraries below the main itinerary if you have more or less time. 

We’ll do our best to give you all the information you need to plan YOUR road trip in Oregon, but if we miss something or you have more questions, leave us a comment below and we’ll do our best to either answer your question, or point you to someone who can.

One last note: We have Portland at the tail end of the itinerary, because it’s a great place to end your epic road trip by kicking your feet up and eating and drinking your way through what we think is one of the best food cities in the country. You could just as easily put it at the beginning, it’s up to you!

Living in Portland, the Columbia River Gorge is essentially our backyard. It takes 30-40 minutes for us to get out there, and when we’re looking for an easily accessible hike for a random Thursday morning, this is generally where we’re heading. 

It’s also on our itinerary for every single first-time visitor who comes to Portland to visit us. 

There is a nice mix of different hikes in the Columbia River Gorge, from easy waterfall hikes to hikes that climb to the rim of the Gorge, where you’ll find dramatic vistas out over the Columbia River and the Gorge beyond. 

Hood River is a town in the Columbia River Gorge, and it is perched at a crossroads of sorts. It sits at the point where the wet, temperate climate of western Oregon transitions to the dry, more extreme climate of the high desert in eastern Oregon. 

To the west, you’ll find some of the best waterfalls in Oregon. To the east, the high desert. And both north and south are the Cascade Range, and places like Mount Hood and Mount Adams. 

There are a bunch of great things to do in Hood River, and that list grows longer when you include the fertile Hood River Valley with its fruit trees as far as the eye can see and the wineries along the Columbia River. 

Hood River is a great home base to use to explore the Gorge and the fertile Hood River Valley, which is what you’ll be doing for this stretch of the itinerary. 

Note that we’ve split the “what to do” sections below into Hood River and the Columbia River Gorge to make it easier for you to plan and group things together. In this case, you’ll hit the Gorge coming from Portland first, then tackle the things around Hood River once you’re already through the Gorge. 

What to Do in the Columbia River Gorge

Here are our favorite stops in the Columbia River Gorge.

Wahclella Falls: This is the best bang-for-your-buck waterfall adventure in the Columbia River Gorge, we think. Multnomah Falls is great, yes, but it’s an absolute zoo at all hours. The short and easy hike out through a canyon with steep rocky walls here weeds out most of the visitors, and you end up at a beautiful waterfall that tumbles off of a ledge into a pool 65 feet below. 

Drive The Historic Columbia River Highway: The Historic Columbia River Highway runs from the town of Dodson, just west of Bonneville (and the dam of the same name), all the way to the town of Troutdale, which is just east of Portland. It’s a windy two lane road that parallels I-84, and is the original road that was used to traverse the Gorge on the Oregon side. Our recommendation would be to drive it from Multnomah Falls to its western terminus, because there are routinely huge traffic jams along the road at the base of Multnomah, and it’s better to park in the big lot along I-84. 

Multnomah Falls: Multnomah Falls is the queen of the waterfalls in Oregon. It’s by far the most impressive waterfall in the state, we think, and it’s actually the biggest tourist attraction in Oregon thanks to its location about 40 minutes away from downtown Portland. It’s a two-tiered waterfall that, all-in, falls 620 feet down from the top of the rocky ledge high above the viewing platform. The only issue we have with Multnomah Falls is the fact that, at any given moment, you’re likely to be sharing the experience with around 1,000 of your closest friends. It’s worth seeing, but there are so many other waterfalls in the Gorge to get to with a fraction of the visitors (especially if you’re willing to hike a little bit). Definitely park at the bigger parking lot along the freeway (here on Google Maps) – the smaller lots at the base of the falls are an absolute nightmare, and we’ve seen massive backups along the Historic Columbia River Highway of people just waiting to get a spot. The bigger lot has more parking, and you just have to walk a few hundred feet to get to the falls. 

Latourell Falls: Lower Latourell Falls is one of the most scenic waterfalls in the Gorge after Multnomah, particularly in the winter when the water level is high AND there’s a bright greenish-yellow moss covering the rocks on either side of the falls. The lower falls is the more impressive, we think, as it falls 225 feet off of a ledge in one single drop. There’s a nice wooden bridge at the base of the falls, which is a short hike from the trailhead, that is a must-do and is a good spot for pictures. There’s a nice, relatively easy two mile loop hike that takes you up to the Upper Falls and down around to the base of the lower falls that is a worthy excursion if you have the time and energy. 

The Vista House & Portland Women’s Forum Scenic Viewpoint: These are two excellent viewpoints at the western end of the Historic Columbia River Highway to cap off a day full of great views. Pictures are worth 1,000 words here, we think, so here’s a few we’ve gotten from up here. 

What to Do Around Hood River

Here are a few of our favorite things to do in and around Hood River.

Tamanawas Falls: This excellent waterfall hike is on the eastern slopes of Mount Hood, and would be a great stop between Government Camp and Hood River. It’s right on Highway 26, and it’s a nice, easy hike up to a spectacular waterfall. Parking is limited, so you’ll want to get there early, or be prepared to wait for a spot in the tiny lot – parking along the highway is illegal, and we’ve seen many people get tickets here. You can find more information about this hike – which is one of our favorites – over in our Tamanawas Falls trail guide.

Drive the Fruit Loop: The Hood River Fruit Loop is a perfect half-day activity near Hood River that takes you through the fertile Hood River Valley, with apple and pear trees as far as the eye can see (with backdrops of Mount Adams, Mount St. Helens, and Mount Hood). There are a bunch of worthwhile stops here, but our favorite is Draper Girls Country Farm, which does u-pick cherries for a short window in the summer, and has all around excellent produce more or less from spring to fall. They have a lovely back patio area with great views of Hood, and a lush collection of various fruit trees. Plus, a wide selection of locally made jams, honeys, and other stuff inside the shop. 

Wine Tasting near Hood River: The area around Hood River, both on the Oregon side of the Gorge, and on the Washington side, is a great place to grow grapes and make wine. There are a bunch of wineries in Hood River itself (Hood River Common House is a good spot), but the real way to do it is to hop in the car and drive out to one of the wineries dotting the landscape around Hood River. We like the Gorge White House (not the best wine and cider, but the setting is amazing) and Loop de Loop (the friendliest wine makers and the best dog, plus an amazing view), and have also heard good things about AniChe Cellars, Le Doubblé Troubblé, and Analemma Wines (this one came highly recommended from the folks at the Ruby June Inn, where we stayed on our recent trip). 

First you hit the eastern foothills, which are notably more dry than the western foothills, and as you continue to Bend and beyond, you’ll be right in the heart of the high desert that stretches across Central Oregon. 

Bend is perched in the eastern foothills of the Cascades, and it is situated between the lush evergreen forests that cover the western part of the state, and the high desert that covers most of central and eastern Oregon. 

Remember at the beginning of this guide, when we said that Oregon is the ninth biggest state in the country? Bend is about 25% of the way from the western border (the coast) to the eastern border with Idaho. Which means the high desert stretches for a LONG time from Bend to the east. 

Bend is perfectly placed between the mountains and the high desert. Within 45 minutes or so, you can be in the heart of the alpine paradise in the Cascades, or hiking through the desert dodging rattlesnakes in Smith Rock State Park (more on that in a second). 

What to Do in Bend

Here are some things to do in Bend, including some of the things to do just outside of town along the Cascade Lakes Scenic Byway. 

Hikes Around Bend: Within the Bend city limits, there are a few good hikes (we’re not counting the hikes in the mountains or at Smith Rock, which we have separate sections for below). Pilot Butte is right in the middle of town, and after a quick ascent you have a panoramic view of the surrounding landscape that serves as a nice introduction to Central Oregon’s geography. To the west, you’ll be able to see the snow capped peaks of the Cascades (there’s a topographic map to help you identify which peak is which). To the east, it’s a lot of flat land. We also have hiked sections of the Deschutes River Trail, which heads south out of town along the river. You could follow the trail for miles and miles, but there’s a nice 2.7 mile loop that focuses on the part of the trail near the Old Mill District that would be a lovely way to spend a morning. It would look something like this. If you want something a little longer, continue south from Farewell Bend Park, which is where the trail gets a little less developed. For more information, read our guide to hiking in Bend.

Explore Downtown Bend: Downtown Bend is centered around Drake Park along the Deschutes River (there are several areas that could be confused as “downtown” so we wanted to clarify). There’s also the Old Mill District, which is a little bit south (and has more chain retailers and Red Robin vibes, if you know what we mean), and the Box Factory, which is between them. In downtown Bend, go to Lone Pine for coffee, The Lemon Tree for brunch (it’s popular so go early), and Bonta for gelato. Then, poke your head into the many shops and boutiques along NW Wall and NW Bond. 

Cider in Bend: If you’re more into cider (we are!), the small town of Tumalo just north of Bend has a couple of our favorite cideries in Oregon, and they’re just around the corner from each other. The first is Tumalo Cider, which has a nice taproom and great, dry ciders. The second is Bend Cider Company, which has a new-ish taproom a couple of blocks away. They do fun flavor combinations featuring fruits and botanicals (but not too sweet!) – we liked the Blackberry Ancho we tried recently. There’s a food cart pod across the street from Tumalo Cider which would make a good stop for lunch between cider tastings.

Tumalo Falls: Honestly, the hike to Tumalo Falls kind of sucks. But the waterfall is cool, so there’s that! It’s a 97 foot high plunge into Tumalo Creek, and if you do the six mile hike, you’ll reach the viewing platform and realize that it’s a five minute walk from the upper parking lot. We’d drive to the parking lot and check out the falls, saving your energy for a more interesting hike (there are many!) later. 

Sparks Lake: We love Sparks Lake. The photo below was taken there on an early summer morning just after sunrise. Head to the day use area, park, and walk along the southeastern shore of the lake, where you’ll be treated to an absurdly good view of the South Sister and Broken Top, with a reflection in the still water of the lake if you’re lucky. 

Smith Rock State Park: With its winding river snaking its way between orange-hued rock formations, Smith Rock looks like it belongs somewhere in Utah or Arizona, not in Oregon. There’s really only one hike in Smith Rock State Park – though you can do it two ways – and that’s the Misery Ridge Trail. It’s accurately named, because the initial ascent up to Misery Ridge is brutal, especially on a hot summer day with full exposure to the sun. The views from the top of the ascent, though, are worth the price of admission. You’ll have a panoramic view of central Oregon, with the snowy peaks of the Cascades to the west, and the high desert stretching out as far as the eye can see to the east. On the descent, you’ll pass Monkey Face, a very popular destination with rock climbers. It is also accurately named, because from a certain angle, this rock formation looks exactly like the face of a monkey. The trail descends back down to the river, where you can either head left to return on the River Trail (shorter and flatter) or right to continue on the Summit Trail (longer with better views and more climbing) to finish the loop. It’s about 30 minutes north of Bend, and you can do it on the way from Hood River to Bend because you’ll drive right by it. 

To add Crater Lake to this particular itinerary, you’re going to want to do it as a day trip from Bend. It’s about 90 minutes from Bend to the north rim of Crater Lake, which doesn’t seem so bad, right?

However, there is one major caveat here, and that’s the fact that the rim road that circles around to the north end of the rim is closed during the winter and early spring due to snow. 

It will start to open in early spring, but when exactly that happens totally depends on the year. 

That’s an issue to keep in mind because Bend is north of Crater Lake. The only way to access the small slice of the park that’s open between November and April (roughly), which is on the south rim, is to enter the park through the south entrance. Which is about three hours from Bend. 

We would only really recommend adding Crater Lake during the summer and early fall (call it June through October) when roads will be mostly open, and hiking trails will be mostly snow-free.

It’s a gorgeous drive, littered with waterfalls, tight switchbacks, alpine lakes, and lava flows. 

There are a few things you need to know about this stretch. First, it’s closed outside of summer and early fall (usually open between July and October).

Second, it’s a narrow two lane road with lots of switchbacks, so it might not be best for RVs or trailers. 

Also, if you follow this itinerary as we’ve written it, you’ll be approaching from the east (coming from the Bend area). We’ve organized the stops from east to west for that reason. 

What to Do Along the McKenzie River Scenic Byway

Here are some stops to make along this scenic drive. 

Sisters: Sisters represents the end of the McKenzie River Scenic Byway, and the beginning of central Oregon and the high desert, which stretches for hundreds of miles to the east until you get into the Wallowas in eastern Oregon. Sisters itself is a cute little town that’s a great base for adventures into the nearby Three Sisters Wilderness. It’s a vaguely western-themed town, with some great spots to eat and drink (Sisters Coffee and Sisters Meat and Smokehouse are good stops) and a cute little downtown area where you can do some window shopping. 

Scott Lake: This pristine lake is one of the spots we’re hoping to return to this summer. It’s a gorgeous lake with a perfect reflection of the Three Sisters (really two of the three sisters), one of the most distinctive natural features of central Oregon, and a bunch of first come, first served campsites along the lakeshore. However, the tradeoff here is the mosquitoes, which are intense in the early summer. For your purposes, we’d park along the lake and walk out to the western shore to get that reflection picture. It’s best in the afternoon, when the sun is behind you. 

The Dee Wright Observatory: As you ascend the tight switchbacks along the road passing Scott Lake, you’ll notice an abrupt change in the landscape. In what seems like a few minutes, you’ll go from dense evergreen forests to an open, rocky landscape. That shift is a result of a massive eruption of the Belknap Crater two millennia ago, and that dark rock stretching out as far as the eye can see is the resulting lava flow. The Dee Wright Observatory is an excellent stop not only to admire the lava flows, but because it gives you a great overview of the numerous rocky peaks surrounding you. This, my friends, is the heart of the Cascades in Oregon, and you’ll see the Sisters, Broken Top, Mount Washington, and Mount Jefferson, along with a handy key atop the Observatory to help you identify which is which. 

Proxy Falls: Over the course of this trip, you’re going to see a bunch of incredible waterfalls, especially as you get into the Columbia River Gorge later in the itinerary. Proxy Falls will likely be in your top three. It’s a short hike – roughly 1.5 miles – that takes you to a massive waterfall that cascades down the mossy rocks into Proxy Creek. You can do a loop that takes you to both Lower Proxy Falls and Upper Proxy Falls. The lower falls is the more impressive of the two, and the view from the base is incredible. 

Newport is the biggest city on the central Oregon Coast, and has the best selection of places to stay, restaurants, and other amenities like grocery stores before you get into the more rural southern Oregon Coast. 

The structure for today is essentially using Newport as a home base to continue your road trip south along the coast past Newport (which is one of our favorite stretches of the Oregon Coast) and then returning to Newport for the night to set yourself up for a long drive the next day. 

Just south of Newport, the coast starts its transformation from the very developed, very tourist-friendly northern Oregon Coast to the more rugged southern Oregon Coast, which is rockier, less-traveled, and offers a little more peace and quiet than places like Cannon Beach and Seaside. 

From Newport, you can hit one of the most scenic drives on the coast – the area around Cape Perpetua and Heceta Head – before returning to Newport for the night to eat some fresh seafood and check out one of the many beaches in town. 

What to Do Around Newport

Here are our favorite things to do in and around Newport. 

Devil’s Churn: A short stop where you’ll hike down to an overlook with a view of an inlet that is partially covered at the end. Which means at high tide, if you’re lucky, the waves coming in will meet the waves going out and create an explosion of water.  

Cape Perpetua: The view from the top of Cape Perpetua is one of our favorite views on the coast, and it reminds us a lot of Big Sur down on the California Coast (at least on a sunny day). You can hike from the lower road up to the top, which is a nice workout, but you can also just drive to the top (which we didn’t know until we got up there, sweaty and huffing and puffing). There really isn’t a reason to do the hike other than a workout – there aren’t any additional views you get by hiking. 

Heceta Head Lighthouse: This is one of the most beautiful lighthouses on the coast, and it’s easily accessible from the parking lot. It sits on a 1,000 foot headland that towers over the Pacific, and they have tours of the lighthouse, a charming B&B in the old light keeper’s home, and tidepools and trails to explore. You can hike out to Hobbit Beach from the lighthouse, which is a nice little trail that follows the coast to a sandy beach. 

Sea Lion Caves: We drove past this place on our first trip, saw a line out the door of a tiny little touristy-looking hut, and said “look at those suckers!” Then we learned what it actually was later on from some Oregonians, and were at least a little bit disappointed that we didn’t stop in. If you want to see sea lions, this is the place to do it. That hut sits over an elevator that takes you down hundreds of feet to the water level, where there’s a sea cave – America’s largest, in fact – filled to the brim with barking sea lions. They’re open 9:00 am – 4:00 pm 363 days a year, and it costs $16 for adults, $10 for kids (under 4 are free!), making it a little bit pricey. 

Exploring Newport: Newport is probably best known for its world-class aquarium – the Oregon Coast Aquarium – which we stopped at and immediately turned around when we saw the flood of small children (it would be a good family activity, though!). There are two lighthouses in town, and the Yaquina Head Lighthouse is at the northern end of town, and is well worth a stop (the Yaquina Bay Lighthouse is less impressive). Definitely head down to the charming Historic Bayfront for dinner and the shops there (here on Google Maps) and head out to Agate Beach (here on Google Maps) for a good view of the lighthouse. 

The drive from Newport to Tillamook is nice, and features a couple of our favorite hikes on the Oregon Coast – Cascade Head and God’s Thumb – which are both worth a stop along the way. 

What to Do Around Tillamook

Here are three things not to miss when you’re in Tillamook. 

Hiking in Lincoln City: Technically this isn’t Tillamook – it’s 30-45 minutes south – but we’re including it here because two of our favorite hikes on the Oregon Coast are in and around the sleepy coastal community of Lincoln City. The first is Cascade Head, which is maintained by the Nature Conservancy (no dogs allowed). It’s a great hike that climbs through the forest and emerges onto a (very windy) bluff over the ocean, which you can climb up for some excellent coastal views. It’s windy as you get out onto the coast, so be prepared. The second is God’s Thumb, which is a short hike from the north end of Lincoln City that takes you out to a point, which looks out over the Oregon Coast both north and south. Along the loop, you’ll pass the Knoll, where you’ll have a view of the never ending sandy beach that stretches out to the south. 

Tillamook Cheese Factory: The Tillamook Cheese Factory is legendary. Not only is there a cool educational experience where you can see how they make the cheese, but there are some truly great food options, including a huge ice cream scoop shop. If you’ve never had their ice cream before, it’s incredibly creamy. That’s their whole thing. The chocolate peanut butter swirl is Alysha’s favorite, with thick, salty swirls of peanut butter tucked into their chocolate ice cream.They also have a retail store here, where you can buy all of their cheeses, including some of their hard-to-find reserve varieties, along with a selection of other local products. If they have them, do not miss their cheese curds, which are only available at the factory and are incredible (we’d never had them before we bought them a few years ago and fried them up post-hike over our camp stove – incredible). 

More Cheese: There’s actually a second cheese destination down the road – Blue Heron French Cheese Co – though we weren’t nearly as impressed with the presentation. The cheese – which leans towards French style – is really good, though. 

We recently went out to Cannon Beach – our first beach foray with our dog, Lupine – midweek in January, and we were basically the only people on the hiking trail in Ecola State Park. It was wet and muddy, yes, but it was so peaceful. 

The highlights in Cannon Beach are actually the state parks that border the town on the north and south end, Ecola State Park and Oswald West State Park.

Sure, Cannon Beach – the town AND the beach – is nice, and you should definitely do a sunset walk on the beach. But definitely don’t miss the nearby state parks.  

What to Do in Cannon Beach

Here are some Cannon Beach highlights that you really shouldn’t miss. 

Hiking in Oswald West State Park: This is the other Oregon state park we referenced above, and it’s equally worthwhile. There are three hikes here to focus your time on. First is the hike to the top of Neahkahnie Mountain, which is an aggressive ascent up switchbacks to a viewpoint where you can see miles and miles of coastline to the south. Second is the hike out to Cape Falcon, which navigates out to the cape on the north side of Short Sand Beach, where you’ll have excellent views back towards the beach. Be aware that this hike is almost always extremely muddy. Seriously, do not underestimate the mud, even in the early summer. Third is the hike – though it’s more of a leisurely walk – out to Short Sand Beach, which is a wide sandy beach (at low tide, anyway) that is very popular with surfers. 

Haystack Rock: It’s cliche, but Haystack Rock really is an impressive sight, especially if you’re not used to the towering sea stacks that you find up and down the Oregon and Washington coast. In fact, we’d argue that Haystack Rock is up near the top of the list of tourist attractions in Oregon, somewhere below Multnomah Falls and above Powell’s Books in Portland. It’s a huge sea stack, rising 235 feet out of the surf to tower over the beach and surrounding community. It’s particularly spectacular at low tide, when you get some cool reflections in the wet sand. On our first trip to Cannon Beach, we witnessed a pair of Bald Eagles raiding the resident puffin colony for their eggs! It was quite the drama, and there are rangers on the beach in the summer who talk about the puffins and the attempts to keep them alive. 

Now, you might be thinking that Lewis and Clark, who had completed their ultimate goal after a significant chunk of time spent struggling west from St. Louis, might have been celebrating with their feet up. 

But their arrival and stay happened to be smack dab in the middle of winter – from December through February – so rather than celebrating with the long, warm days of an Oregon summer, they were treated to constant drizzle and less than eight hours of sunlight. FUN. 

Anyway, Astoria is meaningful in many ways, from the early 19th Century and Lewis and Clark’s antics, to the time when John Jacob Astor tried to make Astoria the New York City of the west (he almost had it!). 

Today, it sits at the northwestern corner of Oregon, and is home to what has to be the highest number of breweries per capita in the country (there’s four or five, and Astoria is tiny), and filming locations for some of the iconic films of the 90’s (the Goonies and Kindergarten Cop, among others). 

What to Do in Astoria

Here are some of our favorite things to do in Astoria. 

Lewis and Clark National Historical Park: Like we mentioned, Lewis and Clark National Historical Park is near the site of Fort Clatsop, which is where they set up camp for three miserable months before heading home to report back to Jefferson. There’s a model of Fort Clatsop here, a bunch of fun information on what life was like on that expedition (and some very charismatic rangers eager to share anecdotes like the one above), and a hike that connects the fort with the coast, a route that they covered many times. However, the hike isn’t really worth too much of your time – it’s 6.5 miles one way out to the coast – we’d do the first mile or so, enjoying the ferny forests of sitka spruce trees before heading back. 

The Astoria Column: The Astoria Column is perched up on the hill above town with a commanding view out over the Columbia River and the famous Astoria-Megler Bridge – that’s the green bridge crossing the river to the Washington side. The Column is an interesting piece of art, because it is wrapped in the story of Astoria. It’s hard to see the artwork when you’re standing at the base looking up at it, but there’s a digital re-creation with labels that is helpful to understand exactly what you’re viewing. You can climb to the top of the column for an even more impressive view of the river. It costs $5 to park in the lot at the Column, or you can park at the base of the hill in town (roughly here) and hike the Cathedral Tree Trail up for free. 

Fort Stevens State Park: This is the northwest corner of Oregon, and also – fun fact – the site of the only attack on a military base in the contiguous United States since the War of 1812 (the Japanese shelled it a few times in 1942). It’s an Oregon State Park, though it was a military base through the early 20th Century. Today, the bunkers are one of the main draws here, and are particularly interesting when there are rangers and volunteers out there to tell you stories about the local history (which is usually on weekends in the summer). It’s worth driving out to the coast and hitting the wreck of the Peter Iredale, a shipwreck on a wide sandy beach, and Clatsop Spit at Lot C (here on Google Maps) where you can walk out along the rocks on the Pacific. 

The Breweries: Two of Oregon’s best breweries are up in Astoria – Buoy Beer Co and Fort George Brewing – and are basically a must-stop for any beer aficionados who find themselves in the state’s northwest corner. They each have a taproom within walking distance of the main drag, and both have food menus and extensive taplists, with many beers you’re not going to find outside of the taproom. In addition, there are a few smaller breweries (like Fortune and Glory Cider Company – technically not a brewery, I guess). Across the street from them is Bridge & Tunnel Bottleshop & Taproom, the best beer bar in Astoria (and a good place to try multiple beers from different breweries). 

The funny part about Portland is that there aren’t really any big name tourist attractions. Seattle has the Space Needle, San Francisco has the Golden Gate Bridge, and Portland has… a donut shop and an independent bookstore?

But, honestly, that’s kind of why we love it. It’s not that there isn’t a lot to do – there’s plenty of amazing things to do in Portland. 

The food scene? The best on the west coast (except for maybe L.A.). There’s a culture of innovation – which we think is at least partially driven by the food cart scene that allows for low-cost experimentation (versus opening a brick and mortar location). 

The access to the outdoors? Between the excellent parks in Portland and the access to the mountains, Gorge, and coast, it’s hard to beat.

We’re in love with our home, and think you’ll like it too. 

Unfortunately for you, your time here is limited, and we’ve intentionally chosen to weight this road trip towards Oregon’s natural beauty, which means you’re left with about a day, maybe a day and a half to explore the biggest city in the state.

If you have an extra day or two, it’s absolutely worth adding time here.  

What to Do in Portland

Now, there are way too many things to list here, so we’re going to focus on our top five here.

Powell’s City of Books: The fact that we’re starting with an independent bookstore – the largest in the world, no less – tells you just about everything you need to know about Portland. It’s right in the heart of downtown Portland, and is an astounding collection of books from all genres. This place is amazing, and even since we’ve lived here I can’t walk out of here without at least one book. I bought a light blue Powell’s Books t-shirt on clearance almost a decade ago that I wear often, and every time I wear it outside of Portland (usually in Seattle) at least one person stops me to chat about how much they love Powell’s. They have an extensive collection of books, including big sections dedicated to fantasy/sci-fi, Pacific Northwest history, and graphic novels. We especially like the staff picks section in the entryway, which is a nice way to see what the staff are reading and recommending at the moment. 

The International Rose Test Garden: Washington Park – which is the park where this rose garden is located – is the best park in Portland, and is home to a bunch of different attractions including the Oregon Zoo and the Portland Japanese Garden. But the Rose Garden, which is both free and spectacular, is the best of the bunch, we think. There are 10,000 roses here, and when they’re in full bloom between roughly May and September (sometimes longer), it’s quite a sight to behold. 

Breakfast / Brunch in Portland: Portland is an excellent food city in general, especially when you consider prices are going to be about 25% lower than other cities on the west coast. However, it really shines in the morning, when you’ll find some world-class breakfast and brunch options. 

Now, you might expect to see Voodoo Donuts on this list. The novelty donuts are fun, yes, but it’s far from undiscovered, and there are honestly much better doughnuts to be had in Portland.

Like, a lot of them.

Go to Blue Star, Doe Donuts, Coco Donuts, or Petunia’s Pies and Pastries (for gluten free and vegan donuts) if you’re in and around Downtown Portland. 

What to Add with More Time in Oregon

Like we’ve said time and time again, two weeks is not really enough time to see everything there is to see in Oregon. Here are a few more things to consider adding if you happen to have more time. 

Mount Hood (+1-3 Days)

Where to Stay at Mount Hood: There aren’t that many places to stay here, but you do want to be in or around Government Camp on the south slopes of the mountain. There’s a Best Western, a campground at Trillium Lake that we like, and a bunch of nice cabins in the woods to choose from. 

Mount Hood is our favorite hiking destination within a couple of hours of Portland. We fell in love with it on that first road trip that eventually led us to move here, and we go back there as often as we can. 

Matt is from Seattle, where the towering peak of Mount Rainier is a near constant reminder of the natural beauty that sits just outside of the sprawling city (and also a constant barometer of the weather – “is the mountain out?” is a common question to evaluate whether it’s a nice day in Seattle). 

Mount Hood plays the same role for Portland, and we often have a similar conversation around Portland around whether Hood is out. 

During the winter, Mount Hood is home to some of Oregon’s best skiing. Then, when the snow melts in the late summer, it turns into a veritable alpine wonderland, with wildflowers blooming, roaring waterfalls, and stunning vistas of Mount Hood around every bend in the trail. 

The part you’re going to want to focus on here is the area in and around Government Camp, on Mount Hood’s southern side. 

That’s where all the action is, though that’s not to say there aren’t worthwhile places to visit on other sides of the mountain. 

By focusing there, you’re also nicely positioned for the next stop on your itinerary, Hood River, where you’ll just hop back on Highway 26 and continue north to Oregon’s northern border. 

For more, read our guide to the best hikes at Mount Hood (because it’s really all about the hiking here, at least in the summer). 

Day Trip from Portland to Silver Falls State Park (+1 Day)

Silver Falls State Park is a hair over an hour south of Portland, and it’s home to one of our favorite hikes in the state – the incredible Trail of Ten Falls. Which, as you might imagine, features 10 waterfalls over the course of a relatively easy eight mile trail. 

If you want waterfalls – and especially if you’re here in the spring and early summer when the water is high – this is as close to a must-do as it gets. 

After your hike, you can meander through the eastern end of the Willamette Valley on your way back to Portland, stopping at Bauman’s and E.Z. Orchards for farms and cider (and apple cider donuts!). 

The tiny town of Silverton is a nice place to stop for lunch after the hike (or just wait until you get back to Portland and check off some other places there!).

If you do want to stay overnight, the campground at Silver Falls is really nice.

However, other than that, there’s really not a whole lot of places to stay nearby, and you’re probably better off making it a day trip and staying in Portland for another night. 

What to Do with Less Time in Oregon

With less time – 7 or 10 days in Oregon – we’d make some adjustments and be more focused with your time. 

With 5 days in Oregon, we’d go ahead and spend the entire time in Portland, doing day trips out to the Gorge, the Coast, and Silver Falls to fill your time (you’d want to rent a car for that trip).

With 7 days, we think you have time for a nice little loop that encompasses Portland and the mountains OR the coast, but probably not both.

If you absolutely have to see both, you could add a day on to do a day trip out to the coast (Cannon Beach or Astoria) or the Columbia River Gorge (Hood River).

With 10 days, you have enough time to comfortably do a figure-8 that includes the mountains (Hood River and Mount Hood) and the coast (Cannon Beach and Astoria). 

Here’s a day-by-day breakdown of what those itineraries might look like. 

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