Most people don’t vacation to Portland, Oregon in the winter. The summer is usually the best time to go. Everything is green and there are a lot of outdoor activities. However, winter is also a great time to experience Oregon. And because of many crazy things which will be explained later, B and I found ourselves in Portland, Oregon in February 2017. Keep reading to see how we saw a ton of what Oregon has to offer in just four days. So here is our winter Portland, Oregon in four days, winter itinerary!
PORTLAND, OREGON IN FOUR DAYS
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WHY PORTLAND IN THE WINTER?
Life in your 20’s can be pretty confusing, right? You are “supposed” to start figuring your life out (by the world’s standards.) Well, my 20’s have been pretty crazy so far. One of the things my husband and I have tried to figure out, is where we want to settle down. Southern California is great when it comes to the beach and heat. However, we would rather find somewhere cooler and cheaper to live.
So last February, 2016, B and I decided to check out Oregon as a possibility. We know it is gorgeous in the summer, but if we want to move there, we have to see if we can handle winter. Spoiler alert: We can’t handle the grey! Oregon is a beautiful state…. to visit! I did not realize that I need sunshine to survive! (Even though I hate SoCal heat!) So, we will not be moving to Oregon. BUT!!! We had such a fun time exploring. It was a fun, quick, 4 day trip. Let me share with you how we managed to see everything on our list!
B and I plan trips… Wait. Let’s be honest, I plan the trips. But, when I plan trips, I do a TON of research beforehand. We pick where we want to explore, and then I hop on Pinterest to research everything about where we will be going. I look up the fun things to do, the MUST SEE places, and of COURSE the food scene. We are serious foodies when it comes to vacations. So when researching Oregon and Portland, there were a lot of awesome places to see in the summer. What I didn’t find much of, was places to explore in the winter. Obviously I could see the reason for that, but we planned it anyway.
If you read my post on How to see Boston in a Day, then you know I use Skyscanner to find flights. I seriously love this website! If you want to know why you should use Skyscanner, click here. They have the best deals on flights and rental cars! If you look on the right side of my page, you can the Skyscanner widget. This is where you can type in details for a flight and see if there are cheap flights! Try it out! You won’t be disappointed.
We also booked an AirBnB which was so cheap! It saved us so much money and allowed us to experience Portland like locals. If you have never tried AirBnB, you should! It’s a great way to save money and travel!
DAY 1: PORTLAND, OREGON
Our flight landed, and we picked up our rental car. We were very excited to be in the rainy weather of Portland, Oregon. I actually love the rain! Probably because it refuses to rain in Southern California so I don’t see it often. But anyway. The first thing we needed to do was eat since we landed around lunch time. So, we headed over to Rip City Grill to get some awesome tri-tip sandwiches.
After lunch, we were still too early to check into our AirBnB, so we had planned a little driving trip to see the area of Cascade Locks.
BRIDGE OF THE GODS: Columbia River Gorge
Cascade Locks is such a gorgeous area! All around us you could see trees, the river to the left, and mountains to the right. At the Bridge of the Gods, there is a small $1-$2 toll to drive across. We thought it was worth it. You basically drive from Oregon to Washington on a really pretty bridge over the Columbia River. There are some beautiful views of Oregon from the Washington side. We could not see Mt. Hood due to the clouds and weather, though.
We were really excited to say we visited two states in the same four-day trip! We explored some of both Oregon and Washington.
I was also super excited about the sign for the Pacific Crest Trail! People who thru-hike that trail are beasts!
Once we finished gazing at the beauty, we drove back over the bridge and headed back to Columbia River Gorge waterfall area to check out the famous waterfalls!
We drove the Columbia River Highway to get to these waterfalls. Because of the rain and the weather, we basically ran up to each waterfall to see it really quick and get a picture. The hiking trails are closed in the winter due to mud from the rain and snow. We were content to just see some awesome waterfalls!
This waterfall is the “most visited natural recreation site in the Pacific Northwest,” USDA Forest Service. There were a ton of people here even in the rain. Of course you have to take a picture of it if it’s basically famous.
I can see why it’s famous though. It’s just so pretty!
Since it was raining, and the trails were closed, we were unable to go hiking to some of the other waterfalls in the Columbia River Gorge. I’m sure it’s gorgeous in the summer though! It was still really nice to drive to each waterfall and see them.
AIRBNB IN PORTLAND
Once it was time to check into our AirBnB, we headed for downtown Portland. It was pretty easy to find and we loved it! I can see why people ride bikes everywhere. We were probably 5 minute outside of downtown, but it felt like a super cute 90’s movie neighborhood! We checked in, and figured out where to go for dinner. That was difficult because there were so many amazing places to eat!
SAUCEBOX FOR DINNER
Saucebox was probably the best place we could have chosen to eat dinner! Thai food has never tasted so good. It was not really that expensive, and the coconut rolls were amazing! If you’re ever in downtown Portland, eat at Saucebox. You won’t regret it. Also, I have to say that this trip was definitely a foodie trip for us. That wasn’t what we planned, but there is just too much good food around Oregon!
POWELL’S CITY OF BOOKS
Of course, being an introvert, I had to check out one of Portland’s most famous bookstores. Powell’s City of Books is the world’s largest independent book store. While walking around downtown after dinner, we walked into this huge bookstore and I was in heaven! I could literally stay in there all day if it was possible. It occupies a whole city block and has 9 different color-coded rooms. You can find new, used and even out-of-print books in this store. It was pretty fantastic.
DAY 2: OREGON COASTLINE
We were going to explore Portland, Oregon in four days. However, we did not just want to stick to Portland. We wanted to explore Oregon in general.
STUMPTOWN COFFEE ROASTERS AND VOODOO DONUTS
Before our long road trip to the Oregon coast, we had to stop by Stumptown Coffee Roasters to try their famous coffee. I usually don’t like plain coffee without tons of sugar and flavor, so I was a little nervous to try their coffee. However, they made me a vanilla latte, and OH MY GOSH! I could drink that every day for the rest of forever! It was fantastic! Plus, I loved the vibe of sitting in a hipster coffee shop acting like I lived in Portland. It was a great moment for me.
And of course, I cannot go to Portland and skip out on the original Voodoo Donut! I mean, coffee and donuts are officially my weakness. We couldn’t pass it up. As we were sitting on the bench outside, I looked across the street and noticed a famous wall! Keep Portland Weird! It was awesome. And let me tell you, Portland is definitely staying weird.
DRIVING THROUGH THE TILLAMOOK STATE FOREST
In order to get to the coast, we drove next to the Tillamook State Forest. It was gorgeous! I am definitely biased and think that the High Sierras are the prettiest forest around, but this is hard to beat! The sheer amount of trees packed into the forest is breathtaking. I can tell why lumberjacks live in Oregon, haha! There are so many trees! And they are so green and peaceful looking.
CANNON BEACH AND MO’S FOR LUNCH
Cannon Beach is a pretty famous beach. We parked in a cute little town and walked out to the sand to hang out for a bit. We got pictures of the amazing rock out in the water.
From what we learned later, we apparently had one of very few sunny days at the beach! There were beautiful clouds, but the sun was out. And apparently, that doesn’t happen often. So we were lucky to have such a great day.
Once we explored the beach, we drove to Mo’s for lunch. We were told by Brandon’s grandfather that we had to eat here! He recommended the clam chowder, and I love clam chowder, so we tried it. We had plenty of food and a great view from our table! It was such a cute place.
TILLAMOOK CHEESE FACTORY
After lunch, you have to eat dessert, right? So we drove further down the highway to the Tillamook Cheese Factory! I was so excited to see this place, and we were lucky they were open. Check times and hours before you go! We were able to see the factory where they make their mouth-watering cheeses. Also, once we walked out into the shop, we were able to taste test the cheese! Oh glorious day. I LOVE cheese!
However, you can’t just go to Tillamook for cheese. They also make to-die-for ice cream! So we tried multiple flavors in a sample-type bowl. It was worth it! The ice cream was heavenly!
After much fun in Tillamook, OR, we drove back in the dark to Portland and relaxed for the night. It was a ton of driving in one day, but it was awesome! Our Portland, Oregon in four days winter itinerary definitely included a lot of driving!
DAY 3: BEND, OREGON AND SNOW
DRIVING OVER MOUNT HOOD
We decided to see as much of Oregon as we could when we were visiting. So our Portland, Oregon in four days became Oregon in four days! Haha. So, today we took off over Mt. Hood to visit Bend, OR. B and I had heard that it was an up-and-coming town with a lot of growth and forests! We would love to live in the woods eventually, so we had to check it out. Bend is about a 3 hour drive from Portland, so we got an early start. Especially in the winter, it is important to see driving conditions when you are going through Mt. Hood. We were lucky and didn’t have too much snow fall on us during our drive. I was driving and had a blast driving through the snow! It was gorgeous! I mean look at this!
B was less enthusiastic since he was not the one driving, and apparently I did not drive the right way through the snow. But it’s always terrifying when you aren’t the one in control of the car right?! So we drove over the mountain and through the woods to Bend. And it was gorgeous!
Bend, OR is such a cute town! There is nothing surrounding it, let me tell you. But, the town itself is very nice. Compared to the rest of Oregon, which is much older, Bend is a clean, newer-looking area. We were actually meeting some of B’s family while we were there. So, while we waited to meet them for lunch, we walked around downtown and this cute little pond. We decided it was too cold and too far away from everything for us to live there. However, it is very cute with a lot of activities near-by.
We had such a nice lunch visiting B’s family! We didn’t stay very long due to the sunset. B wanted to make sure we weren’t driving over a mountain pass in the snow after the sun went down. So we headed out back to Portland, this time coming up from the South end. We definitely drove through more snow, and once again I was enthralled. It’s just so beautiful when the whole world looks white! This time B was driving and I was the one terrified! But we headed back to Salem for dinner.
Once we stopped in Salem, OR for dinner, we found a place in downtown with a lot of food options. However, it was all pretty expensive and the food did not look like something we would enjoy. B was afraid a lot of it wasn’t enough to fill him up. For some reason, we also got a very weird vibe from Salem. I can’t explain it, but it was weird. So instead of settling on a place to eat, we decided to head back up to Portland for dinner and find something there. I don’t know what it was, but neither of us liked Salem that much. Sorry Salem! I’m sure you’re an awesome town, but just not for us!
TASTY N SONS AND SALT AND STRAW
Once back in Portland, we found an awesome restaurant called Tasty N Son’s. It is described as a “new American diner.” They serve a lot of craft beer of course and have interesting things on the menu. We figured the food looked tasty, so we tried it out. We got a great seat at a bar style table looking out the window to the street. Since it was raining, we had such a good time talking and watching people go by. Portland, to me, is just very pretty. So anyway, the food was awesome! They serve everything al-a-carte. So we were able to try various things. All the food was great and we were happy with our choice.
Right down the road, we walked to dessert! Salt and Straw! I had heard, before coming, that this place has the best ice cream ever. Well, B and I love ice cream. So we had to try it and decide for ourselves if it really was that great. Lucky for us, they let you taste however many flavors you want before buying one. So we tasted many, many flavors. All the flavors were delicious too! They had such eclectic flavors like honey lavender, pear and blue cheese, and Arbequina olive oil. Of course B had to get Freckled Woodblock Chocolate. My favorite was Sea Salt with Caramel Ribbons. I’m a sucker for salted caramel lately!
So, I will have to agree, it was some of the best ice cream I have ever tasted. Even compared to Tillamook ice cream I tried, it was fantastic! Anyone in Portland has to go try it out. After indulging in our delicious ice cream, we walked back to the AirBnB since it was so close to all the food! It was in the best location. Then we got some sleep for our last day of exploring before heading back home.
DAY 4: VANCOUVER, WA AND HOME
BLUE STAR DONUTS AND DUTCH BROS COFFEE
When we were thinking about coming to Portland, I became a foodie. I usually am a foodie, however, Portland is filled with too much good food to not eat all of it! I had always wanted to visit the original Voodoo Donuts, and it was great. However, when I was researching, so many people kept saying that Blue Star Donuts was better. Of course, I had to find out if this was true, so on our last morning, we headed over to Blue Star Donuts. On the way, we had stopped for Dutch Bros Coffee and were busy drinking away. Once we walked into Blue Star Donuts, the man behind the counter almost kicked us out! He was so offended that we would bring that terrible coffee into his donut/coffee shop. He was totally joking with us of course. But he said he would let it slide and let me buy a donut. He said at least it wasn’t as bad as Starbucks. So we got lucky there, haha.
Blue Star Donuts had extremely eclectic donuts in my opinion. They have a green tea matcha donut, a Meyer lemon and key lime curd, a raspberry rosemary buttermilk, etc. They are extremely different flavors and they make them all with natural ingredients. I ended up ordering the coconut creme donut and it was very tasty. Apparently, Blue Star Donuts has come to Manhattan beach and Venice in Los Angeles. So now you don’t have to go all the way to Portland to try one!
OVER THE BRIDGE TO VANCOUVER, WA
After our awesome breakfast of coffee and donuts, we drove over the bridge to visit Vancouver, Washington. We drove around to see if maybe we liked this area better than Portland. Sadly, we didn’t like it better. So we won’t be moving to the Pacific Northwest anytime soon. However, because it was raining and we were close to flying home, we did not do much in Vancouver but look around.
Portland, Oregon in four days was great even if it was in the winter. I think four days is a good amount of time to see much of Portland and the surrounding areas. We had a good time and learned a lot. (I always learn a lot when I travel.) I would love to go back and visit in the summer when there is good hiking and everything is different shades of green. Because we got such a great deal on plane tickets by using Skyscanner, we just had to go! Click the link below to find super cheap flights and go on an adventure! Trust me, it’s so much fun!