Category: Oregon
Author: Michael DeFranceschi •

The 14 Best Things for the Ultimate Weekend in Portland-- From Someone Who Used to Live There [2023]

#6 is a trippy one! Keep Portland weird!
US travel blogger Michael DeFranceschi in front of some colorful street art in southeast Portland


Hey-- I'm sure the Portland in Maine is cool-- but we're talking about the real Portland here! The one in Oregon. The city who inspired the quirky comedy series Portlandia.

I spent four wonderful and memorable years living in Portland. At age 26, I relocated to the Rose City with no job and only a little bit of savings. Within three weeks, I had myself a full-time job, an apartment, and began playing open mics in the vibrant Portland music scene.

In late 2019, I moved back home to Michigan but later revisited my old stomping grounds in October 2021 during my 'visit all 50 states' adventure. Oregon was state #14.

The Pacific Northwest is one of the most beautiful spots in the United States. In many regards, I think Portland is the most unique and interesting major city on the west coast. Unlike Los Angeles, Portland rarely feels disingenuous. People are proud to be themselves in Portland-- no matter how different that may be.

Portland is proud to have been integral in the Seattle grunge scene that exploded in the early 1990's. Today, Portland is still well-known for its inclusive and diverse music scene-- hence, the big reason why I decided to move there years back.

When it comes to food, Portland really is a shining star. Of all major cities in the United States, the city is the most catering to vegan and vegetarian diets. Even for omnivores, Portland is a mecca for foodies.

Portland is one of the few cities whose nickname derives from its airport: PDX. Portland International Airport is one of the cleanest and charming airports in the country. In fact, it is my second favorite airport in the US.

For being a major city, Portland is especially easy to navigate due to the city dividing itself into four quadrants-- southwest, southeast, northwest, and northeast-- each quadrant with its own personality. Also, there is just a "north" section of the city.

Allow me to put my four years of residing in Portland to the test as I present to you my list of the 14 best things for the ultimate weekend in Portland!


In 2023, here are the 14 best things to do for the ultimate weekend in Portland...

01 // Take a picture of your feet at Portland International Airport

Inside the Mall of America with a 'Mall of America' sign above. Entrance to Nickelodeon Universe is visible in the background
My shoes could use a bath!

I'm not joking-- this is seriously a thing that lots of people do at Portland International Airport (PDX). If you're flying into Portland, this will either be the first thing or last thing you do on this list!

Throughout the airport is this green carpeting with red, yellow, and blue strokes as part of the design. Something about the color scheme of this carpet has compelled visitors over the years to take pictures of it with their shoes in the shot.

A simple fun gesture like this is one of the reasons why Portland has the reputation of being an eccentric city. Don't be in a rush at the airport and miss your opportunities to prove to others you were at PDX!

To avoid feeling rushed at the airport, read my article here on the numerous benefits of TSA PreCheck®.

02 // Eat the best donuts in the country 24 hours a day at Voodoo Doughnut

Inside the Mall of America with a 'Mall of America' sign above. Entrance to Nickelodeon Universe is visible in the background
A rare sighting at Voodoo Donut is an empty line!

Seriously-- you have no idea what a rare sighting this is. Chances are, when you go to Voodoo Doughnut, there will be a line outside the doors. Likely, a long line too!

There will be a few other items in this article pertaining to food. Voodoo Doughnut is among one of the reasons why Portland is the best city in the United States for foodies. The pastries here are better than any donut chain, like Tim Horton's or Dunkin Donuts. Everyday, their donuts are made fresh-- and it really shines through in its superior quality.

Another attribute which adds charm to this 24-hour eatery is its crudeness. The shop has two suggestive slogans: 'The Magic Is in the Hole' and 'Good Things Come in Pink Boxes'. Two doughnuts it serves are named 'Old Dirty Bastard' and 'Cock n Balls'.

My personal favorite doughnut there is the 'Oh Captain, My Captain'-- a ring doughnut with vanilla frosting and Cap'n Crunch cereal.

While it may be punk rock ethos to resist accolades from the mainstream, Voodoo Doughnut has embraced praise of its product and brand and been featured on television shows like Good Morning America, The Tonight Show, and The Amazing Race.

One more factoid about this Portland staple is-- it has its own record label!

Some Portlanders who hate on Voodoo Doughnut for being too tourist-y will claim that Blue Star Donuts is better. Blue Star Donuts is pretty great too-- better than Dunkin or Tim Horton's. And... there is a Blue Star Donuts inside Portland International Airport!

Address: 22 SW 3rd Ave, Portland, OR 97204
Hours: 24/7

03 // Visit the largest independent bookstore in the U.S-- Powell's Books

Outside Powell's Books in the Pearl District of downtown Portland.
This bookstore will make a reader out of anyone!

Even if it's been a long time since you've sat down and read a book, you have to visit Powell's Books.

Located in the Pearl District, which is a more ritzy and gentrified neighborhood of downtown Portland, Powell's Books is allegedly the world largest independent bookstore. It possesses a charm and atmosphere similar to The Last Bookstore in Los Angeles.

Powell's selection of books is unrivaled even by chains like Barnes and Nobles. The independent bookstore has six floors of literature, spanning any niche genre you can think of. Browsing Powell's gargantuan selection of reading material is much of the fun!

Be sure to check out the coveted 'rare book room'. You have to sign in at a desk and receive a nametag before entering and only a small number of people can be inside the room at any given point in time. The room has books dating all the way back to the 12th century. As expected, many of the books inside the room sell for several thousands of dollars.

There is a cafe inside the bookstore with several large benches and tables with chairs-- very much like a cafeteria. It's a great place for people to read and work on their own projects.

Address: 1005 W Burnside St, Portland, OR 97209
Hours: 10:00 a.m to 9:00 p.m

04 // Visit the Saturday Market

The intersection of SW First Ave and SW Ankeny in downtown Portland where the Saturday Market is held every weekend.
The market also operates on Sundays! Source: Shutterstock

With the exception of the months of January and February, the Saturday Market runs every Saturday (and Sunday!) from 10:00 a.m to 5:00 p.m. Yep-- albeit being named the Saturday market, you can catch it on Sundays as well!

And how perfect to visit this event, since you too are visiting on a weekend!

Whereas Powell's Books is the largest independent bookstore in the world, the Portland Saturday Market is the country's largest continously running arts-and-crafts fair.

The Portland Saturday Market houses a wide spectrum of artwork, including but not limited to: jewelry, paintings, sculptures, photographs, clothing, and rugs, from Portland-based or nearby Oregonian artists. Many talented street musicians add to the artistic atmosphere with creative renditions of popular songs or original music.

Whereas many fairs will serve more standard Americanized food like burgers, pizza, and hot dogs, the Portland Saturday Market has lots of multicultural food options to choose from.

Another asset of the weekly arts-and-crafts fair its location: it is very close to the Willamette River, which gives visitors a stellar view of not only the water but also Portland's many bridges. While Portland does not have as many bridges as Pittsburgh, the bridges nonetheless add to Portland's beauty.

On a final note, the Portland Saturday Market is extremely easy to reach if you ride the Red or Blue line of Portland's MAX train. Get off at the Skidmore Fountain stop and you won't miss the fair.

Address: 2 SW Naito Pkwy, Portland, OR 97204
Hours: 10:00 a.m to 5:00 p.m (Saturday, Sunday)

05 // Go behind Dante's to find an iconic quote

Behind a music venue called Dante's is the iconic 'Keep Portland Weird' mural.
And the quote is... 'Keep Portland Weird'!

Sorry-- I couldn't keep which quote a secret very long because of my picture!

After getting the best doughnut you've ever had at Voodoo Doughnut, head across the street for this next item.

Located behind a local music venue named Dante's is a mural with a quote that perfectly describes the spirit of Portland. From what you've read already, Portland is weird-- in a very good way! From a doughnut shop having its own record label to a Saturday-named market also operating on Sundays, Portland is unabashed in its quirkiness.

Speaking of the building who sports this photoworthy mural, if you're in the mood for some great live music and want a good taste of Portland's local music scene, catch a show at Dante's. It's one of the more difficult venues for Portland musicians to get in (I know this from personal experience) so the bands and artists who perform here are usually quite good.

Address: 350 W Burnside St, Portland, OR 97209
Hours: 11:00 a.m - 2:30 a.m

06 // Hear your own voice surround you at Pioneer Square

Behind a music venue called Dante's is the iconic 'Keep Portland Weird' mural.
Me seated very close to the spot in Pioneer Square where you stand to hear your own voice.

I didn't have this blog when I visited Oregon and I really wish I asked the friend I was visiting to shoot this photo horizontally, like most of the photos I use.

Pioneer Square is a public park is in the heart of the southwest quadrant of Portland-- much of which is considered 'downtown'.

In front of the steps you can see me sitting on is this spot where, if you stand just right and speak out loud, you will hear your own voice 'surround' you. It's akin to being in a wide, empty room and hearing your own echo, though, in this case, the reverberation is instantaneous. Some wizardry I can't explain in the architecture produces this acoustic effect.

There is a really cool sign in Pioneer Square which tells you how far various things are from the sign-- such as Casablanca, Manhattan, or the 'Portlandia' statue.

Since Pioneer Square is such a focal point of downtown, you'll find some animated people around it for sure. It's often an epicenter for political activism or, perhaps surprisingly, Christian evangelists.

True story: I once met 2020 presidential-hopeful, Andrew Yang, outside the Starbucks on Pioneer Square. Here's the picture to prove it!

Address: Just type 'Pioneer Courthouse Square' into Google Maps
Hours: 24/7

07 // Eat at a food cart

**(image coming soon!!)**

Eating in Portland can easily be its own series of articles, which I will eventually write.

For your short time in Portland, you need to eat at a food cart! Food carts are a huge staple of Portland culture and the food served as these carts are oftentimes superior to many sit-down restaurants.

So now, the big question you're probably asking is: which food cart do you suggest??

In my opinion, many of the best food carts are located in southeast Portland. I'll start you off with a cluster of food carts collectively known as CARTOPIA. The cuisine currently includes Thai, Latin, American, Egyptian, pizza, and a cart that focuses on sweets.

I am a sucker for some good mac-n-cheese so another recommendation which is also in southeast Portland is Herb's Mac n Cheese.

The food carts are all over the city and it's hard to go wrong. Try one (or multiple!) out!

08 // Consume alcohol inside a school

**(image coming soon!!)**

I don't tend to recommend bars much since I'm not much of a drinker but Kennedy School is something special. It's considered to be a hidden little gem of Portland because of its camouflaged location and is something only someone who's lived in Portland a while would know about.

To an outsider walking by, the establishment looks identical to a school. It is only once you head inside that you see it's a hotel & bar with an elementary school as its theme! You can go inside a 'classroom' and drink beer. It's a really fun way for drunk adults to emulate the feeling of being a naughty little kid.

This unique bar is located in the northeast quadrant of Portland. At this point in the article, we technically have listed something to do in every quadrant.

Address: 5736 NE 33rd Ave, Portland, OR 97211
Hours: See here

09 // Visit the Japanese Garden

**(image coming soon!!)**

If you want a short break from the city and want a sample of Oregon's natural beauty, this item and the next will satisfy that desire!

The garden has a truly authentic Japanese aesthetic-- with its shrines, intimate and tranquil stone-paved walkways, streams, and purple flowers. There is also a tea house you can visit on the campus as well! This garden is so true-to-life that even a former ambassador of Japan to the United States visited the grounds and noted how genuine and beautiful the garden is.

The Portland Japanese Garden is located in the hills of Washington Park-- so there are points where you can get a breathtaking view of much of the city.

There is a cost of admission and it is worth every penny. A regular adult ticket is priced at $19.95.

Address: 611 SW Kingston Ave, Portland, OR 97205
Hours: 10:00 a.m to 3:30pm (closed on Tuesdays)

10 // Explore Mt. Tabor

**(image coming soon!!)**

Mt. Tabor is a public park in southeast Portland that was built on top of an extinct volcano.

The park is 191 acres-- so yeah, it's pretty damn big and there's no way you'd see all of it just visiting for a weekend.

Mt. Tabor is simply beautiful. There are plenty of walking trails with tall cascading trees. Due to its elevation, you can get some stunning birds-eye views of the city. It is a place you visit when you want to explore nature and get out of the city but also don't want to go too far from the city.

Portlanders are very lucky to have such amazing natural beauty so close to the city. And believe me-- Mt. Tabor doesn't even compare to other natural wonders throughout the state.

The park is accessible from the Trimet bus system.

I went to Mt. Tabor several times when I used to live in Portland and considering the frequency of my visits, I'm surprised I don't have more to say about it. Go there, experience what you can of it, and I'm sure you'll wish you had more time for your trip so you can see more of it!

11 // Wander around the four quadrants of Portland

Entrance to Chinatown, in SW Portland.

As a city explorer, one of the easiest and yet most enjoyable ways to immerse yourself in the concrete jungle is to just meander. Walk around. Even though I lived in Portland for four years, during my re-visit, I still freely explored.

As I stated in the introduction of this article, Portland is easy to navigate because the whole city is divided into quadrants-- southwest, northwest, southeast, and northeast. Each quadrant has its own look and vibe.

'Southwest' Portland is the business center and, thus, most corporate and city-looking quadrant of Portland. Much of southwest Portland is referred to as 'downtown'. One thing you'll notice though in the downtown of this west coast metropolis are the lack of skyscrapers. Unlike, say, Minneapolis, most of the edifaces in downtown are of modest height.

The next two quadrants-- 'northwest' and 'southeast' are what most people think Portland looks like-- that being, a really big small town.

Finally, northeast Portland is the most suburban looking part of Portland, which is why it is my least favorite.

All four quadrants are so easily accessible due to Portland's amazing public transportation system. The three modes of public transportation are the MAX trains, the streetcar, and the buses. I would encourage you to not rent a car when exploring Portland and, instead, to walk and utilize the public transportation.

12 // Make a day trip out to Multnomah Falls

Multnomah Falls, with the Benson Bridge. Source: Shutterstock.

Okay-- I am technically cheating by including this one since neither of these spots are in Portland, but ask any Portlander and they'll agree that going to Multnomah Falls is totally worth it even if you're visiting Portland for a weekend.

Even though I just said for the last item that you shouldn't rent a car when exploring Portland, you'll need one to get to Multnomah Falls. Fortunately, it is not a long drive and should take you only around 30 minutes to get there.

It is the tallest waterfall in Oregon-- at a height of 620 feet. You can hike up to the top but the trail is not for beginners. Parts of the trail can get quite steep-- and slippery if you try to hike it in the winter time! I once did it in the middle of January-- at night too-- when I lived in Oregon.

As seen in many pictures of the falls (including the one I used for this article), there is a bridge called the Benson Bridge where people can get some amazing pictureesque views of the falls. Getting up to the bridge is not too difficult and is doable for most.

13 // See if Portland has the best coffee

A consequence of having not taken a picture of the coffee I had in Portland is I'm having to use a stock photo. Source: Unsplash

Portlanders are proud of their coffee and have a rivalry with its neighbor city, Seattle, for who has the better coffee. Like food carts, there are so many cafes throughout Portland that it's rather tough to recommend one.

Go somewhere in southeast Portland and pick one. Try the coffee. I myself can at least attest the coffee is quite good. The best? I don't know coffee well enough to make that judgment. Perhaps you do!

Even if you conclude Portland's coffee isn't #1, going to a cafe is still something anyone visiting Portland should do. The cafes in the city are manifestations of the city's values, personality, and spirit.

14 // Eat at Burgerville

**(image coming soon!!)**

A few items on this list have revolved around food and drink. After eating a doughnut from Voodoo Doughnut and dining at a food cart, you'll get a good idea as to why foodies adore Portland so much.

There are some fast food restaurants exclusive to certain states. Like Swenson's in Ohio, Burgerville is a fast food burger restaurant that is only to be found in Oregon and parts of Washington. Their burgers are pretty great and I'd easily assert their burgers are tastier than the burgers belonging to larger chains like Wendy's, Burger King, or Whataburger.

If you forget to stop at a Burgerville in the city or don't have the time to, don't fret-- there is a Burgerville in Portland's airport.

And a reminder-- while you're at the airport, if you want to compare and contrast the doughnuts between Voodoo Doughnut and Blue Star Donuts, there is a Blue Star Donuts location inside the airport!

Is Portland good for a weekend trip?


You can definitely visit all four quadrants of Portland in one day. You can even make a trip out to Multnomah Falls as well since it is only about 30 minutes by car from the city.

If you are flying in from the midwest, south, or east coast of the U.S, bear in mind the duration of your flight will be anywhere from 5-9 hours. Thus-- if you work a typical 9-5 job, you might want to take a Friday off work and have your flight be as early as possible to maximize your time there!

What is the best month to visit Portland?

I would suggest May or June and here's why:

Portland is most rainy and cloudy in its late autumn to early spring months. Like Seattle, Portland has a reputation for being a rainy city. While it doesn't rain as often as rumors suggest, it feels like it rains a lot because from late autumn to early spring, it may drizzle most days of the week.

If anything-- Portland should be more known for having a lot of cloudy days. It has around 222 cloudy days per year.

As for the summer months, Portland can get a bit hot for some. Temperatures in the 90's are becoming increasingly common. Thus, I would say May or June is your best bet if you want some sun, low chance of rain, and to not be scorched by the sun!

Is Portland worth visiting now?

Portland did take a whallop in 2020 and 2021 due to COVID and civil unrest-- downtown, in particular.

That being said, Portland is still a wonderful retreat for a weekend getaway in 2023!

Is 3 days in Portland enough?

Yes-- for most weekend getaways, I would definitely vouch for 3 days being a sufficient duration.

Is downtown worth visiting?

Yes-- even though downtown did get hit pretty hard by COVID and civil unrest, downtown Portland has 4-5 items on this list alone. Many of Portland's most notable attractions are found in downtown.

That said, most people think Portland is a 'big small town' and to see that aesthetic, you should go to southeast and northwest Portland.