“She Flies With Her Own Wings”
(State Motto of Oregon)

Just like Oregon seems to have been made for road trips, the state motto is the perfect manifestation of the innovation and independence that drives people who are from Oregon, and the feeling you get when you visit.


Trillium Lake sunrise

There’s no better feeling than creating a playlist, connecting your phone to Bluetooth, rolling the windows down and hitting the open road on a new adventure. The road trip is a signature adventure everyone should experience at least once in their lives – and Oregon is a state almost created just for this purpose.

There has also been a lot of discussion recently about people choosing to fly for their trips, how much carbon is created from those flights (especially if they are not direct), and the responsibility to offset your flight. I’m never going to be the person to tell anyone not to fly, but if this is something you are genuinely concerned about my suggestion to you is to think about the ultimate summer past time for your upcoming adventures: the road trip.

The good thing about Portland is its location within the state. Give and take a few minutes (which is completely dependent on exactly where you are going) it only takes an hour to get to the mountain, and hour and a half to get to the beach, and hour or less to get to wine country, and hour or less to get to the gorge. 

Oregon itself has a wide variety of terrain and environments – and can feel like you are in 3 different states all within the same location. This was one of the things I came to appreciate during my time in Oregon, and why I tried as often as I could go on a road trip adventure (or by public transportation if available)!

Visiting the Columbia River Gorge from Portland

The Columbia River Gorge could arguably be called one of the most famous state lines in the US. Separating Oregon from Washington this canyon spanning over 80 miles offers a multitude of activities for those wanting to get active outside.

Crown Point pano

There are numerous hiking trails, which are starting to reopen following 2017’s Eagle Creek Fire. Arguably one of the most famous waterfalls in the state is also located in the gorge, Multnomah Falls (which also features a hiking trail), and there are over 90 waterfalls in total just along the gorge.

Multnomah Falls

As you make your way farther east you on highway 84 (the main road you will be taking) you come upon multiple viewpoints. Two of my favorites are Crown Point and Rowena Crest. Crown Point sits over 700 feet above the river and features the Vista House building which was built in 1916. Rowena Crest is one of those famous Instagrammable places, due to the winding road you take to get to the top of the viewpoint. Once at the top there are a handful of hiking trails you can take around the rim which give you specular views looking both east and west along the river and over to Washington state.

Rowena viewpoint Washington
Rowena Crest Viewpoint

Not much farther east down highway 84 is Hood River, the “adventure capital of Columbia River Gorge”. This city has a small town fell, great dining options, a super chic hotel, outdoor activities such as windsurfing (which this city is known for), and the popular ‘Fruit Loop’.

The Fruit Loop is a 35-mile scenic drive through the Hood River Valley featuring 36 stops that include farm stands, wineries, breweries, alpaca ranches, lavender farms, and more. Not everything is open year round but the best time of year to go is between May and October. This way you can pick what you want to see and experience, whether it’s apple picking and cider, corn mazes, wine tasting, or lavender fields.

One of the bonuses of visiting the Columbia River Gorge is it is a place you can go without a car! The Columbia Gorge express bus runs daily from the Portland metro area, making it the perfect day trip for people who visit Portland without a car.

Visiting The Oregon Coast from Portland

Depoe Bay pano

The Oregon Coast is a place that you will dream about long after you have visited. The coastline is long and is definitely not something you can do in one day but luckily there are a good handful of famous points that you can combine together into one easy day trip – many of which are located along the central coast, into the northern coast.

I could go on and one about all of the points you need to hit when visiting the coast, but the thing is, when you are short on time you can’t fit everything in, unfortunately. Let’s be real though, Haystack Rock is probably the main reason you had the coast on your radar, this Cannon Beach landmark draws visitors all year round, and when the tide is low you can even see tide pools at the base of the rock!

Cannon Beach Haystack Rock stairs

Tillamook is a must if you have never been to the Oregon Coast, simply because there is where you can visit the factory that makes that delicious (and very well-known) cheese and ice cream. Make sure you take a factory tour so you can sample the squeaky cheese curds!

oregon coast pano

Pacific City is another beach that has a haystack shaped rock, within the Cape Kiwanda State Natural Area, but is slightly more off the radar when it comes to people visiting from out of town. There is a massive sand dune that you MUST climb up in order to get the ultimate view of the rock and the sea, and you can even go horseback riding on the beach!

Pacific City horseback riding
Devils Punchbowl top view

Lincoln City is one of those towns that has a good handful of things to do but is also conveniently located near other towns that make it an ideal place to stop during a road trip. If you are visiting from mid-October through Memorial Day there is a chance you may find one of the 3,000 handcrafted glass floats that have been hidden on the seven miles of public beach in the town. Devils Punchbowl State Natural Area is a crown jewel for wildlife spotting and is very close to Lincoln City. There are tide pools, starfish, you can go into the punchbowl when the tide is low and search for crabs, and you may even spot grey whales! But, if seeing a whale in person is on your Oregon Coast bucket list then you have to head just slightly farther south to Depoe Bay, the “Whale Watching Capital of the Oregon Coast”.

If you decide to continue heading north, then Astoria and Warrenton definitely need to be on your list. This area is the western end of the Lewis and Clark Trail, is the oldest American settlement west of the Rockies, is where the movie The Goonies was filmed, and is also where the Peter Iredale Shipwreck is located, within Fort Stevens State Park.

Visiting the Willamette Valley from Portland

There are many things synonymous with The Beaver State – nature is something that usually comes top of mind. But, I will argue that wine is also something that comes top of mind when thinking of Oregon, and if it doesn’t, it should.

There are more than 1,300 wineries and vineyards scattered throughout the Willamette Valley, so you know you are going to get one of the best wine educations here. And one of the best parts about the valley is its proximity to Portland. You can easily be at an award winning vineyard after driving only 30 minutes.

No matter what your preference you can be sure that you will find a wine of your liking within the valley, and if wine is not what you are after there are a handful of other things to do – no drinks required.

The city of McMinnville is the heart of the valley and has a main street with cute shops, delicious restaurants and drool worthy cafes. The Evergreen Aviation & Space Museum is the home of Howard Hughes’ Spruce Goose. And if you love animals the Alpacas at Marquam Hill Ranch is a place where you will make memories to last a lifetime (to the amazing tune of $10).

Feeding alpacas at Marquam Hill Ranch
Marquam Hill Ranch alpacas

But if you came to the Willamette Valley to wine taste, woohoo!, then make sure you bring plenty of water to keep you hydrated for this full-day affair. Some of my favorite places to visit are Adelsheim (because of the founders, David Adelsheim, is one of the early pioneers of Oregon Pinot Noir), Alloro Vineyard (because it feels like you went to Italy), The Eyrie Vineyards (because their Pinot Noir beat out French competition at a Paris wine tasting competition in 1979), and Durant Vineyards Winery & Tasting Room (because the property is gorgeous, and they also have an Olive Mill on site), and Fairsing (because the views are amazing and they have a little labyrinth).

Fairsing chair view
Adelsheim vineyard grapes

Visiting Mt. Hood National Forest from Portland

Mt. Hood is part of the Cascade Mountain Range which runs from Washington into Oregon. Although it’s not a national park like its neighbor Mt. Rainier, Mt. Hood provides unparalleled beauty no matter the season.

Mt. Hood Dog Mountain viewpoint

If you’re visiting during the warmer months, then you must spend the afternoon at one of the more than 150 lakes that lie within the boundaries of the Mt. Hood National Forest – my favorite is Trillium Lake. If hiking is more your speed you will find no shortages of hiking options for all skill levels. I haven’t done a huge amount of hiking up near the mountain but two of my suggestions would be Dog Mountain or the Zigzag Canyon overlook trail at Timberline Lodge (if you have a buddy to go with) and if you are going solo I would recommend Tamanawas Falls Trail. Also if you are visiting the mountain during the summer months then you must visit Ski Bowl to ride the Alpine Slide. Going during the winter? Then snowshoeing, inner tubing, skiing, and relaxing with a warm beverage at Timberline Lodge (filming location of the movie The Shining) is a must.

Trillium Lake
Mt Hood Zigzag trail
Tamanawas Falls hike

Another must see that lies within the Mt. Hood National Forest are some hot springs. Hot springs are definitely an experience you need to have while in Oregon because they are a great way to get in a hike, have some relaxation time and connect with nature. Many of the hot springs are local treasures so people aren’t too keen to share their favorite spots, but one I can tell you about is 
Bagby Hot Springs. This is one of the more popular hot springs due to its proximity to Portland and the fact that you’re not actually sitting in a hot spring, running the risk of damaging the landscape. The location features a handful of tubs that are fed by the hot spring water which you fill and adjust to your liking with the cold river water that is also available.

Bagby Hot Springs Mt. Hood
Mt. Hood Tiny Home Village

If you decide that you can’t get enough of the Mt. Hood National Forest, even though this is a road trip focused post, then I would suggest you get the full unique experience of this outdoor mecca and stay in a tiny home.

Visiting Bend / Central Oregon from Portland

I struggled with whether or not to put this on the list due to the amount of time it takes to get to this area of the state, but realized some people are more epic than others, and three hours really isn’t that long if you’re up for it! After all, I have gone up to Seattle and back in one day, which was also 3 hours one way.

Smith Rock State Park Monkey Face
Painted Hills large hill

Bend is an outdoor activity mecca. There is a reason that so many people relocate here from the Portland area and surrounding states. If you love being outside, love being active, love beer, and love a more all-around chill vibe then Bend is a place you must hit up!

If you are going to make the drive out to Bend I suggest you plan your trip accordingly. Make sure you leave early in the morning (no later than 9:00am) in order to maximize your afternoon and early evening. Even better, would be to leave earlier than that in order to be in Bend by 10:00 or 11:00am.

Smith Rock State Park is a huge must if you are visiting Bend. This park has a handful of trails, wildlife spotting galore, you can take part in the famous activity of rock climbing, and even horseback ride in the park! The terrain in Smith Rock is out of this world and it actually made me feel as though I had stepped on set in the HBO show Westworld.

smith rock pano

Now on your return drive to Portland I am going to suggest something that sounds a little crazy, but I did it so I know it’s possible. I would highly suggest you make a quick stop at the John Day Fossil Beds National Monument and check out the Painted Hills, one of the 7 wonders of Oregon. If you want to spend a good amount of time exploring the hills and the fossil beds then you are going to need more time, but if you want to snap a couple of photos at these geological marvels then you’ll only need an hour or so.

Painted Hills Cove boardwalk

Speaking of the 7 wonders of Oregon, throughout this post of awesome day trip ideas, I covered 5 of the 7 wonders (Smith Rock State Park, the Columbia River Gorge, Mt. Hood, the Columbia River Gorge, The Oregon Coast), so you’re well on your way to be a seasoned Oregon traveler!

PS – I won’t judge you if you turn this day trip into an overnight trip.

Painted Hills overlook

Alaska may be known as the last frontier, but Oregon is THE frontier you need to explore on a trip out west, and there is no better way to do it than on a road trip. If life is a highway there is no better place to discover life’s adventures than in Oregon.

stay wild + curious!
xo, lindsey