What Makes Portland Special

Well, first of all, I am pretty sure we went during the most perfect time of year because: Fall Colors. We got SO lucky with the weather as we didn’t have any rain save a few drops while we were cozy and asleep. So we got all the Fall beauty without freezing or getting soaked.

To me, Portland has almost a New England vibe, mixed with a big dollop of hipster, a dash of Victorian and coated in equal parts quirk and charm.

Portland Neighborhoods

There are so many different neighborhoods and each has it’s own feel. We spent most of our time exploring downtown “old town” Portland. It is much smaller than I was expecting and so walkable! There is so much history and the buildings all hold so much character, but a lot of it has also been maintained really well/updated. It was so cool to see a building built in the early 1900’s holding an insta-worthy coffee shop or chic restaurant. I noticed almost all the restaurants have big glass windows in front. This not only lets you see the vibe and style of the place when walking by but also the people dining and having a grand ol’ time. It made me want to stop and eat everywhere we passed!

Portland Culture

Mark and I also couldn’t get over how CLEAN the city was. We commented on it several times. No trash on the ground, clean sidewalks, no grafitti. Of course, these were also the areas we were visiting but it was still impressive. The people of Portland take a lot of pride in their city, it’s heritage, and the respect is clear.

It is also a super progressive city and almost every business had a sign in the window proclaiming all races, religions, sexual orientations, gender identities etc were welcome. I mentioned this to my mom and she said it was sad we are living in a time it’s necessary to state things like that however, I disagree. I thought it was so beautiful that the people of Portland were making such a strong statement about who they are and what they value. It shouldn’t have to be said, but I’m SO glad they are saying it.

Portland Neon

Another thing I couldn’t get over was all the neon! So many places in Portland have unique neon signs. You may be familiar with this one as it’s the most famous- but there are so many cool neon moments around every corner! It was just as fun to drive around and sight see at night as it was during the day because buildings you may not have noticed in daylight POP with their neon in the dark.

Portland Food

Oh, and can’t believe I’m mentioning this last here but THE FOOD. OH. EM. GEE. You guys. The food was spectacular! Portland is a foodie haven! Mark and I went into this trip with no plan and a bunch of recs from you guys, but the first day we arrived we were hopping around based on yelp while working on our laptops. Literally everywhere had 4 – 5 stars and hour long waits- it was insane! The waits were deserved as we did not have a bad meal while in Portland. Read on for alllll the deets of where to eat while visiting…

Where to Eat in Portland

Kure Juice Bar

Yes, we landed in Portland and immediately our LA came out and we sought out green smoothies. Mark and I had work to do so we busted out our laptops, asked for the wifi password and slurped down our delicious and very green smoothies. A lot of the food in Portland is very heavy and rich so if you’re looking for a breather from that this place is it. They have some delicious looking bowl situations too but Mark needed “a his-size meal” so we headed on to…

Bamboo Sushi

This is a small chain that is in alsmost every neighborhood in Portland. Normally when I hear “chain” I’m out- but it was gooooood. Think Katsuya level chain vs a TGI Fridays. Every roll we got was absolutely unreal. We did a Garden of Eden and Friday the 13th among other items. Nothing disappointed. Very unusual flavor profiles, combinations and all the seafood is sustainable. Can’t go wrong.

Tasty N Alder

Hi. This was outrageous. One of the recs we kept getting was Tasty N Sons. However, Mark and I basically didn’t leave our little block of 23rd the first day and it just so happens Tasty N Alder was right there! They are the same owners and similar menus. OMG everything here was SO delicious.

We originally tried showing up around 4:30 to get an early dinner because we are grandparents, but they don’t actually start serving dinner until 5:30p. They have lunch, and then a break where you can get some light bites at the bar, then dinner at 5:30p. We opted to explore a little more and come back for dinner. They don’t take reservations and we got there at 6 to put down our name and were seated at 7. I’m telling you guys this Portland food scene is hopping!

Mark had been here the last time he was in Portland and insisted on starting with the Raddichio with bacon lardons, Manchego and a six minute egg. SO GLAD WE DID. Highly recommend. I’ve never tasted anything like it. We also did the brussels sprouts, rib eye, and I think a risotto moment. I can’t remember but everything was fantastic You can’t go wrong, I promise.

Barista

Day 2 of exploring started with coffee/tea and breakfast burritos at Barista. I opted for a Chai Latte with Oat Milk and was thrilled that Portland is just as bougie as LA because when I requested Oat Milk they didn’t bat an eye. I have found my people. Mark got coffee as he should because Portland and the PNW in general is known for it. I had a sip and it was so flavorful and rich.

I have to say though, the highlight of Barista for me was the breakfast burritos! It’s a takeaway place, so they’re pre-made but they toast them to perfection where the outside it crispy but the inside is warm and gooey. My fav type of food item. I went veggie and Mark had some kind of chorizo situation. Mine was better, obviously. I am always a better orderer than him and don’t let him tell you otherwise. Get the veggie.

Escape from New York Pizza

We were exploring with friends one of whom grew up in Portland. This was his go-to, must-have pizza place so we stopped in late-afternoon for the boys to have a slice. It’s authentic New York by-the-slice pizza and I get the hype. Thin, super crispy crust, gooey cheese, lots of grease. It’s a local joint that has been rocking since the 80’s so they must be doing something right. I had a bite of Mark’s slice and it was definitely delish. Not the number one thing I would recommend when visiting but if you’re having an old-school pizza craving this will 100 hit the spot.

Southpark Seafood

How did we manage to eat like 17 dinners while in Portland for 3 nights? We are just dedicated like that. Mark is the bougiest housewife you’ve ever met so the whole weekend he was bitching about needing oysters. NEEDING them. He was in NYC the weekend before and had some there he loved {did I mention, bougiest housewife} so he HAD to get some more on his palette stat.

There were actually a lot of highly rated oyster places in Portland but this was closest to the pre-wedding welcome reception so we landed on it and I’m not mad about it. Claim to fame is the “best clam chowder in Portland” which has gnocchi in it {Whaaaaa?!}. That was very good but I have to go housewife bougie too and say the oysters were better. We did a variety of 2 dozen and they were def some of the best oysters I’ve ever had. The Caesar salad and shrimp and grits were some other amazing standouts.

Barlow

This was where the pre-wedding cocktail welcome was held and it was so cute! It’s basically comfort food gone bougie {as much of Portland is} and we noshed on charcuterie boards and mac and cheese balls while sipping some DELISH cocktails. I was throwing back too many “Summers Ago” and if you get this drink watch out because it’s dangerously delicious. Highly recommend popping in here for a few cocktails to set your night off right.

Pine State Biscuits

Ya’ll. I saved the best for last. After a strong wedding go Saturday night we managed to squeeze in one last highly recommended spot on our way to the airport: Pine State Biscuits. Stop it right now.

Mark and I were slightly hungover-pants and in desperate need of some comfort food. Comfort us it did and all out we went. This is a Southern-Fried-Down-Home-Biscuits-And-Gravy kinda place. You’re not worried about macros here, Boo Pigs. Don’t try. Mark and I love ordering all. the. things. and sharing. We went with the below. All must-haves.

The Reggie Deluxe: Biscuit breakfast sandwich with fried chicken, bacon, cheese, gravy and an egg

The Moneyball: Biscuits & gravy with an over easy egg

Fried Green Tomotoes

Bourbon Caramel Cinnamon Roll

You need all of these. You probably need more than these. If I lived in Portland I would weigh 300 pounds because I would eat here every day. Must Go.

What to See in Portland

Powell’s City of Books

If you are a book lover like me this is your ultimate fantasy. This bookstore takes up an entire city block and has special sections for banned books, unusual staff picks etc. There is room upon room of incredible new and used books!

I was in search of “And Then There Were None” by Agatha Christie for our book club- the index showed they had a used copy in addition to new but I couldn’t find the used on the shelf. Went to one of the many info desks and they took my name, book and announced on the store-wide intercom for staff to search for the book for me! In about 5 minutes I heard my name being announced again, “Caitlin, please come to the Green room your book has been found!” It was such a cool experience! I went to collect my book and they had brought several other vintage Agatha Christie’s with gorgeous covers they thought I may be interested in. YES PLZ. Snagged one, obviously.

Washington Park

My friend who’s wedding we were attending recommended we explore the Goose Hollow neighborhood as she knew I would love the old estates there. The neighborhood was so cute, like- these houses were MADE for carving pumpkins. I kept saying if they didn’t have pumpkins on their porch they should be kicked out.

We were just planning to drive around an explore the homes when we dead ended into Washington Park AKA my Fall colors dreams come to life. Over 400 acres of nature including an arboretum, archery court, rose garden and more. We drove the winding roads and ooed and ahhed over the STUNNING Red, Orange and Yellow trees while rocking The Nightmare Before Christmas soundtrack, obvi.

It was a magical drive and I recommend it highly especially in the Fall season!

Pittock Mansion

This is a gem hidden in the hills above Washington Park. First of all, you had me at Mansion. Not a hard sell.

Victorian, 46-room mansion built for a newspaper tycoon in the early 1900’s. You can buy a ticket to tour the inside but we opted to explore the free gardens and sweeping views of all of Portland all the way out to Mt Hood. Even just the outside and gardens are absolutely gorgeous and well worth an afternoon stroll though. One of my trip highlights for sure!

Slabtown/Alphabet District NW 23rd

This was a top recommendation from my Insta babes as they know my vibe and knew I would LOVE this area. They were so right! NW 23rd runs through what is known as Slabtown or Alphabet Historic District and it is such a walkable area of gorgeous historic buildings, chic shops, boutique restaurants and more.

We drove through at night the first night we arrived and it was all lit up with white twinkle lights {the best!} I knew we had to come back and explore in the day time. We came back the next day to stroll up and down wandering into shops large and small- all equally charming. Definitely plan some time to explore this neighborhood.

Where We Stayed

Okay kids, this was by far my number one asked Insta question because BOY did we luck out. We ended up staying at a friend’s home in Lake Oswego, about 8 miles outside of Portland. The home we stayed at was on the lake itself which is an absolute stunning private lake lined with the most insane homes I’ve ever seen in my life. Unbelievable. If you have a way to get access to the lake I can’t recommend it enough. Our friends took us all around the lake on their boat and it was absolutely one of my favorite experiences of the weekend.

If you can’t do that, downtown Lake Oswego is absolutely adorable and does have an area to walk up to at least see a portion of the lake. We also did some hiking trails which gave us views of the lake and gorgeous homes! A cute little respite outside of Portland itself.

Overall Feels

Really can’t recommend visiting Portland enough. It’s one of my new favorite cities and I would definitely go back to explore more, maybe in the Summer next time! Have you been to Portland? Please let me know any favs we missed this go round so I can visit next time! I already have a list started from all your fab Instagram recommendations.

Xx,

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