Keep Portland Weird/ A Touristy Guide

Portland, Oregon travel guide | Girlfriend is Better
Photo courtesy:

Let’s just say I was super impressed with Portland this last trip out. I’ve never really gotten in to the city and checked it out, which is unfortunate. I’ve been missing out! My brother invited me up for the weekend, so I started doing some research online. I read up on Portland’s hot spots and tourist traps (I like them both). Being from Southern California, I am a stone’s throw away from culture and entertainment. I’ve gotten kind of spoiled in that respect. Portland surprised me with a very cool culture, genuinely nice people, and vintage stores galore!

Record shops galore! | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy:

My Handy-Dandy List for Portland

First of all, when I travel to a city that I’ve never really explored, I do a bunch of light research online. When I get to my destination, I always get advice from the locals on the latest and greatest. Usually people will touch on a few points I already have on my list and then will add some fun additions I didn’t know about. This is how I test if their advice is worth listening to!  I also recommend booking your stay using Airbnb.  Many times hosts will have some pointers on local coffee shops or restaurants that can’t be beat!  And it’s much cheaper than a hotel.  Use this link to save $40 off your next Airbnb trip!  Terrific if you would like access to a kitchen, which is a money-saver, too.

Portland Oregon travel guide | Girlfriend is Better
Photo courtesy:

Zines still exist in this super cool city.

Props to Portland for keeping zines alive and kicking. I was so stoked to find a big collection when I was doing my initial research. The zines I found are illustrated and contain unique takes on the best finds in the city. Check them out!

Portland Oregon Zines | Travel guide | Girlfriend is Better

  1. Portland Pizza Guide, where you can find the best artisan pizza locations
  2. Feminist Guide to Beer Drinking, featuring women-owned Portland beer businesses
  3. PDXXL, which contains all of the best roadside attractions in Portland (including a giant duck, a rotating statue of a milk carton, and a 31-foot-tall statue of lumberjack Paul Bunyon)

Day Trip on the Coast – Easy!

The rad thing about Portland, is that the airport is right on the Oregon/ Washington border. It’s about a 2-hr drive to the coast, which makes for a great day trip. Not to mention the drive is gorgeous. Massive pine trees lining the highway and little rivers and lakes along the way. Once you get to the coast, the pine trees don’t stop and it’s got the same beautiful qualities that I love about Big Sur.

Portland Oregon and it's beautiful bridges | Travel Guide | Girlfriend is Better
Photo courtesy: sparrowfoot

Hey You Guys!!

We took my nieces and nephew up to Astoria and saw the Goonies house. There are signs all around the neighborhood that say “Access closed to Goonies house!” (posted by the poor people who have had their lawns tromped on over the years by sightseers). Of course, we considered ourselves an exception to the rule and very politely got our token photos and went on our merry way. Turns out the kids hadn’t even seen Goonies! My brother didn’t even realize! We ended up having a Goonies movie night that night; those poor kids – it was all kind of lost on them.

Check out the Goonies house in Astoria | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: From up North

Bridging the gap between Oregon and Washington

After the Goonies house, we had lunch and then drove over to Cannon Beach to see Haystack Rock (spoiler alert! where the Goonies surfaced from the cave and watched the pirate ship sail away). The beaches are so beautiful and different from Southern California. I loved it. There are bridges all around the area, and we were in one state and then the other throughout the entire weekend. So, I scored a trip to Washington and Oregon with one super cheap flight! (Check out the Hopper app – it lets you set destination and time frame and sends you alerts on travel deals).

Portland Oregon travel guide | Girlfriend is Better
Photo courtesy:
Music Alert! Here’s an oldie but goodie – I thought it was well-suited for a Portland bit 😉
Press “Listen in Browser” to play immediately.

Portland’s Making it Rain Everyday

No matter when you go, be ready for non-stop rain. I learned that Portland is considered to be a “temperate rainforest”. This means it’s super green and constantly raining. If you go just kind of prepared for it, it is quite fun for a couple of days 😉 Like a typical California girl, I under-packed with a green hooded windbreaker as my rain-repellent. A windbreaker worked pretty much perfect until the end of the second day, when it could take no more and sadly started absorbing water. Lesson learned – something in a similar weight would be perfect – just needed to be more water-proof.

Note: If you opt for a raincoat, the locals will certainly know you’re from out-of-town because they don’t wear hoods or use umbrellas or anything. They just go au natural love-me-or-leave-me style. I didn’t care, but just letting you know if you want to blend in. I kind of like sticking out like a sore thumb when I travel. Maybe it’s a safety mechanism ;p

NightingaleArtwork poster | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Portland Oregon Umbrella Letterpress | Art by: NightingaleArtwork

Voodoo Donuts For Your Guilty Pleasure

The next day, we decided to explore the city (AKA walk every square block of the place until we were satisfied) and this is where my handy-dandy list came into play. We took the train in, just for fun, and then walked down to Voodoo Donuts – a touristy must-go. They’ve got a line out the door non-stop, but it moves pretty quickly.

Voodoo Donuts | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Amanda Green Bottoms

Once you’re inside the tiny shop, you can view the menu packed with all sorts of crazy concoctions. I of course had the “Triple Chocolate Penetration” donut (much to my brother’s chagrin), which was the yummiest chocolate donut with chocolate frosting and…Cocoa Puffs on top. Sometimes it’s surprising the things we find delicious. Sometimes not.

Other donuts available are the “Gay Bar” (cream donut and rainbow Fruit Loops), the “Old Dirty Bastard” donut (with chocolate frosting, Oreos, and peanut butter), the “Bacon Maple Bar” donut (with maple frosting and bacon on top), etc. You get the idea. But no matter how crazy they sound, they are really surprisingly, amazingly good.

Voodoo Donuts | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy:

In another life, I may be homeless.

One of my favorite things about Portland was taking in the city itself. Right across the street from Voodoo Donuts is the infamous “Keep Portland Weird” wall. Interestingly, Portland is a city where many people are homeless by choice! They seem to have a little sub-community going that I found interesting. And strangely compelling.. Kind of nudged my inner Jack Kerouac.

Gina Speed in front of Keep Portland Weird wall | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Joey Delli Gatti

Paper + Vinyl

Portland is also a place where you can still find book stores and record stores! Hooray! You can bet I was stoked to rummage through both. The biggest book store is Powell’s Books. Powell’s Books has two main locations – one on Hawthorne and the one we went to on W. Burnside. It’s a couple of floors and takes up a whole block. You can’t miss it. I also don’t want to alarm anyone, but there is a Dr. Martin’s store right across the street. Are you feeling what I’m getting at? This whole town was sort of 90’s heaven for people who still read and love music. People like you and me.

Vinyl is forever! | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Dazed

Support Portland’s Local Artists

Further down to SW 10th (a block away), I found my favorite tiny boutique, Tender Loving Empire. Make sure you connect with them on your next trip to Portland. Pick up some local vinyl, artisanal goods, bath organics, jewelry, or in my case a souvenir. They had these fun metal coasters in the shape of Oregon with hearts cut out in the Portland section. Perfect Valentine’s Day gift for my friend from Oregon. Done and done!

Bring an umbrella! | Portland Oregon travel guide | Girlfriend is Better
Artist: Marco Pece; “umbrella” | Photo courtesy:

OMG Food Carts

If you’re needing food, another unique feature of the city are the food carts. Portland food carts basically offer a variety of authentic ethnic foods that make for a great lunch. My brother’s favorite cart is Chez Dodo, located in Square Market. It’s the only Mauritian themed cuisine in the city, which is inspired by French, African, Indian, Creole, and Chinese cuisine. My brother has tried almost every cart on the block and said you really can’t go wrong.

Food carts | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: A Lady in London

Please Be Sure to Hit a Local Vintage Boutique

After lunch, we Ubered down Hawthorne Street to check out a line of vintage shops to finish the day (thanks local girl for the great advice!). They were super thrift-style and I blazed through most of them until I got to Vintage Pink – a pink store housing over 20 vendors carrying mid-century furniture and décor. Super legit. We spent a lot of time perusing the different vendor setups and checking out stuff. It was like sneaking into the coolest homes for just a peek without getting caught! I still dream of that place.

Vintage Pink vintage shopping | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy:

Further down the street, we ended at Magpie, which had the best selection of vintage coats, dresses, and furs on the block. Their stuff is mostly from the 60s and 70s and we spent quite some time going through racks of rad apparel. I’m glad I ended on those high notes and will definitely hit that street up again earlier in the day and with a big suitcase waiting to be filled.

Portland Oregon skyline at night | travel guide | Girlfriend is Better
Photo courtesy:

Tip: Find Your Local Hipster Nightlife

Finally, the pièce de résistance food cart dessert experience happened in the most hipster-y food cart section I found. Now these guys are on to something – I loved it! We went to Perierra Crêperie, which is on the corner of Hawthorne and 12th. It’s got the big yellow duck perched on top, so you can’t miss it.

There’s a couple of other food carts on the corner and they form a little plaza with a fire pit and lights strung overhead. It felt like a total date-night venue. And please, what’s not to love about a huge folded cone of crêpe, strawberry, banana, Nutella, and rum? The clientele was easy on the eyes and I think this would be an area for young marrieds or singles to check out (for future reference).

Food carts at night | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Joey Delli Gatti

Overcoming the Roadblock of Regret: “Next Time”

As you may have noticed, I was loving that 90’s fashion peeking out everywhere in an “I actually grew up in the 90’s so I know what I’m doing” sort of way. Very nicely done. My list did initially include Chinatown, which is supposedly the nightclub hot spot, so I’ll have to do another trip up and explore that aspect. I was most interested in Holocene (who was doing a “Dance Yrself Clean” Friday night and a Sweater Beats Saturday night) and a girlfriend also recommended Whiskey Library if you’ve got 99 problems.

Portland sign | Portland Oregon travel guide | Girlfriend is Better
Photo courtesy: Cool HDR (Chris Pokorny) on Flickr

So any other good suggestions I would love to hear because this city hit my Top 5 list for the USA! Be a pal and leave a comment below – I’m planning on heading back soon! If you go, let me know as well – I want to hear about your trip.

12 thoughts on “Keep Portland Weird/ A Touristy Guide

    1. Thanks Kristina! I can’t wait to go back and find more 🙂 It’s such a great city. The Marco Pece umbrella art installment was actually created in Italy in 2009. It paints a perfect picture of how I view Portland though. Always raining!

    1. Agree! Let us know if you have any favorite restaurants, etc. when you go. I need to plan a trip back again soon as well. And Seattle!

  1. Going out there next week to house hunt. Have to decide on Nashville or Portland. This is going to be a difficult decision.

  2. Thank-you for this list! My boyfriend and I are headed back to Portland for our 3rd time. You must go to mothers bistro for brunch and Gravy. Gravy has the best French toast I’ve ever had in my life!! Also if you are a fan of arcade games quarterworld on Hawthorne is an awesome barcade. Happy travels!

    1. Thanks for all of the great tips! I’m going to try and plan another trip closer to Spring Break as well. I will def. give all of these places a try. Gravy sounds amazing.. and I never would have thought to check out an arcade. What a fun idea! Travel safe and have fun exploring 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *