If you want a taste of hipster United States, there’s no better place to go than Portland, Oregon! It has the perfect mix of a college atmosphere and a young professional vibe. Whatever you’re looking for, this Portland Bucket List will have you loving the city!
Note: none of the links are affiliate links in this post. I am simply providing the location for any information you might need for an awesome trip to Portland!
How Portland Works – What You Need to Know
Portland is a bit of an anomaly, at least when it comes to US cities. If you stay in the city center, take advantage of one of the most well-connected cities in terms of public transportation. I did not have a car, and I rode the light rail from the airport to downtown, and then to the bus stop, and do all of these just by walking and riding the Trimet light rails (see below!). Portland was designed to be walkable – so it really, really is.
The city’s downtown is split into quadrants. The Willamette River goes North-South, splitting Portland into East and West. The central road Burnside Street splits the city East-West, and it defines North and South. Pick up any map and it will be clearly labeled; addresses are sometimes also split into NW or SE halves – so pay attention to where you need to go!
Into and Out of Portland
The most convenient and accessible way into the city is through PDX – the Portland airport. The Trimet light rail red line goes directly to it, which is super useful!
You can also take trains or buses, or drive yourself. Amtrak is a good option for trains. Bolt Bus (I took this from Portland to Seattle!) or Greyhound buses are also a great option. All the stops are located in the city center, which is extremely convenient if you want to travel locally. The train and bus options usually take you to Seattle and Vancouver in the north, and can bring you as far south as Los Angeles, but over several days. You should probably stop in San Jose or San Francisco before continuing on south.
Places to Go: Portland Bucket List
Portland is great because it’s a nice mix of nature and city. The city streets are often covered in tree shade, and there are stretches of parks that go between some of them. It’s really nice if you are walking in the summer and don’t want to be in the sun all day, or you just want to be reminded of the nature beyond tall buildings.
Saturday Market + Skidmore Fountain
The Saturday Market – open on both Saturdays and Sundays, March through Christmas Eve – is a must if you’re in town on the weekend! It opens at either 10 am on Saturdays and 11 am on Sundays, and is a hub of bustling activity. You can find everything and anything that screams “PORTLAND!!!” I spent several hours here, eating all kinds of great food from the stalls (gyros, curly fries, and elephant ears, anyone?)! I browsed through incredible art for sale. You can buy anything from lavender everything (soaps, shampoos, and car fresheners) to photos and paintings to novelty items like a hat that makes it look like you have a giant knife in your head.
Check out the Sights & Sounds of the Portland Saturday Market!
There are tons of people around, making music and performing, and children playing in the fountain. You can bring a towel to sit down for a picnic or just grab something to eat and keep walking!
Pro tip: Buy your food not on the side of the market closest to the river. Go inland towards the light rail tracks, because those stalls sell the same foods but often $0.50-$1 cheaper. Also, bring cash because most places won’t take credit card.
Mills End Park
Not so exciting in person, but Mills End Park makes my Portland Bucket List because it’s in the Guinness Book of World Records! That is, for being the smallest park in existence. You can barely put a foot in it – which I would not recommend because you would squash the little tree that it has. It’s located in the middle of the street at 56 SW Taylor St., and you can just pass by it. Some people will leave little lego figures or other tiny things to help it feel more like a real park.
Pioneer Place/Pioneer Courthouse Square
If there is anything that you want to buy, you should be able to go here to get it! Pioneer Place Mall includes stores such as Starbucks, Apple, H&M, and Microsoft. The Square, right across the street, is a gathering place for big events in the city or exhibitions. If you do the Portland Walking Tour (see below), the starting point is here.
One of the cool things you can notice is the tiles that have names written on them. Someone who wanted to help pay for Pioneer Courthouse Square donated each of these tiles. If you’re interested, you can purchase one as well!
Washington Park (Oregon Zoo, Japanese Garden, International Rose Test Gardens)
[Recommended Read: The Ultimate Guide to Portland’s Washington Park]
If I had to compare Washington Park to another in the US, it would be Central Park in New York City. Even then, Central Park is far from the size and grandeur of Washington Park. You can get to it by Trimet light rail, as parking spots and traffic tend to be a giant hassle on weekends. The Washington Park stop will take you to the south entrance, where the Portland Zoo and Children’s Museum are. From there, they have free shuttles that can take you to each of the attractions at the park!
Most people come to the Park to see the International Rose Test Garden. It is a huge expanse of land – one of the largest in the world and FREE(!) – dedicated solely to all varieties of roses. The great thing is you can touch and smell all of them, take pictures and enjoy the variety, mix of colors, and elegant perfumes of the flowers.
They claim the Japanese Garden is one of the most authentic outside Japan, and I can vouch for that. Entrance tickets are not cheap at $14.95 for adults (as of Summer 2017), and you may have to wait in line – I waited more than 20 minutes. The entrance is worth it if you have never been to Japan, or are an aficionado and want some great pictures. They have beautiful plants and a small waterfall that make for great photos, but if you’re short on time or have been to Japan several times, you can skip it.
Portland State University
This is the one place I did not personally go, but PSU has a gorgeous campus with plenty of lawn space for picnics or lounging around. You can sign up for a free tour here.
Things to Do
Go Shopping + Buy Luxury Items
The best thing (arguably!) about Oregon is the absence of sales tax (extra tax you pay for everything that you buy)! Unlike in other states where you have sales tax of 9%+ (COUGH COUGH CALIFORNIA), you can save a ton on sales tax if you buy your luxury items here. There are plenty of stores in Pioneer Place and all around downtown Portland. Or, you can go to Woodburn Premium Outlets in Woodburn, about 40 minutes from downtown Portland.
I went to the Apple Store at Pioneer Place to replace my old phone. The phone cost me $749 exactly. If I were to buy it in Texas, my home state, I would have paid $61.79 in tax. In California, where I was before Portland, I would have paid $71.16. Add on to the fact that I bought the phone online through a miles shopping portal and earned an extra mile per dollar I spent on Apple.com, I got a pretty good deal!
Visit the Portlandia Statue
Though not as recognizable as some other iconic city statues, Portlandia is a symbol of Portland through and through. The reason it’s not shown in media or on merchandise is because the statue is copyrighted. The artist based it on the design of the city seal, and it sits atop the Portland Building on SW 5th Avenue. It is a stop on the Portland Walking Tour (see below!), and the best view of it is from across the street. They have a set of escalators that can take you to the second floor, from which you might be able to get the best view of the giant statue.
Admire Public Art
Portland city law requires that any building project in the city set aside a small percentage of the budget, dedicated for public art. This means there are over 400 art pieces downtown – all for your admiration and free! Sit down to admire whatever you pass by, or download this Public Art PDX app (Apple only!) to go on a public art-finding mission.
Take a Portland Walking Tour
[Recommended Read: Review of The Best of Portland, Portland Walking Tour]
Walking tours are one of the best ways to get to know a city! While I generally recommend free walking tours, Portland doesn’t seem to have a great free tour. Instead, they are served by Portland Walking Tours, which currently has 7 different options for tours, including their cultural Best of Portland tour that I went on!
They take you to some of the best parts of town, and the other tours allow you to eat some of the best food, drink the best beer, and even understand the underbelly of the city. The tours are a bit expensive (the Best of Portland was $23, and they are very clear they expect tips as well), but I figured it was worth it.
The group registered about 15 people, but they split us into 2 groups. Some people didn’t show up, so my tour was just 4 people. I definitely learned a lot about Portland – and the tour was much more entertaining than reading a plaque at a museum or reading Wikipedia at home.
Visit Powell’s Books
Powell’s Books is one of the most well-known independently-owned bookstores in the world! In fact, it is the largest independently-owned bookstore in the world. It’s right in the middle of town, and you can find just about any kind of book you want. The whole store takes up the entire block and several stories. You can spend a whole day in there reading, drinking coffee, and picking up some tourist information for your own Portland Bucket List. It doesn’t have the best places to just lounge around and read. But, they do have an “Espresso Book Machine” that can print out any book you want on the spot!
Use the Portland Trimax light rail and streetcar public transportation systems
Portland’s public transportation rivals Asian and European cities. Instead of sprawl, downtown is compact and accessible with Trimax light rails and streetcars! Get a map from Powell’s Books or the airport, and take a ride. The Trimax light rail is an honor system; no one checks to see if you bought a ticket. All stops have ticket booths that take cash and credit. It’s best to buy a $2.50 ticket to avoid fines in case someone comes along to check.
Even if you walk most places, the light rail is great for some trips. Washington Park and the PDX airport, for example, are a bit far from downtown but have direct stops!
Admire Portland City Planning – and Street Tiles
Part of the walkability of Portland is its city planning. Blocks are walkable in just several minutes, and streets are straight enough you can look all the way down without having your view blocked. There are large windows on most buildings, and awnings can’t extend too far from the building. All of these add up to make a very comfortable walking experience!
In certain squares, like Pioneer Courthouse Square, citizens funded the area by buying tiles. That’s why they have individual names, and you can look down to see the community effort for all those squares.
Take a photo of the “Keep Portland Weird” mural
As an Austin, Texas native, I loved this mural! Portland has lots of public art, and this is the only must-visit on my Portland Bucket List. Keep Portland Weird is a play on Austin’s city slogan, “Keep Austin Weird.” It encourages residents should support local businesses. Many, many people equate Austin and Portland (hipster vibe, lots of farmer’s markets, fun place for young people, food trucks, etc.) so this is a visual representation of that connection.
Visit the Oregon Historical Society Museum and “The Portland Penny”
Though I did not visit the museum, I saw the Portland Penny on display as part of the Portland Walking Tour. The museum is located in the arts district of the city, near the arts and theater buildings, and can easily be incorporated into a “culture day”. There is striking street art right around the building, and a fascinating story behind the penny!
The founders of Portland, Francis Pettygrove and Asa Lovejoy, wanted to name the city after their hometowns. They decided to flip a coin, and Pettygrove won 2 of 3. As a result, they named Portland, Oregon after Portland, Maine! The Oregon Historical Society Museum displays the coin they used.
Rent a public bike
If you prefer not to walk or take public transport, you can find a public bike! They are all around town in bright orange bike racks. At the moment, the system is not the most efficient. You have to find one of the bike racks and return the bikes to another, but as the system grows it should become easier and easier to use. Portlanders (Portlandians?) are hipster enough to be ahead of the curve.
Things to Eat & Drink
Portland is known for being a “foodie” town. While I am not one myself, you can’t visit without eating or drinking these! You should never have to settle for a bad or even “okay” meal!
If you’re a beer aficionado, do a brewery tour. There are a million options, or even pick a bar that brews its own beers right in the restaurant! I went to 10 Barrel Brewing in the Pearl District since the family I have in Portland wanted to try the beers. They have their beer vats right next to the seats, and a rooftop bar with a great view! We got the 10 beer sampler, which has large shot glasses of 10 different brews. My uncle loved the IPAs to ales to stouts to porters – not that I have any idea what the difference is. Since I was with family, they didn’t card me, even though I know for a fact I look about 18!
I had never heard of these before arriving to Portland – specifically, the Saturday Market. If you go there, it seems every food stall sells them. Elephant ears are basically giant crosses between pancakes and crepes. The original flavor means drenched in cinnamon sugar, but some of them have other toppings. They make a nice dessert – but I would recommend sharing with someone because it does get to be a little much.
Water from a Benson Bubbler
One of the characteristics of Portland are the public water fountains that are constantly overflowing with water. When I first saw them, I thought that there was some sort of leak – until I noticed that all the fountains were constantly bubbling. They’re called Benson Bubblers, and they basically allow you to avoid touching water fountain handles by always having a stream of water. Bizarre, but very Portland-esque.
I was not that impressed with Voodoo Doughnuts, to be honest, but it’s still a must-eat. Every Portland Bucket List has them. They sell all kinds of novelty doughnuts, all basically just decorated very cutely. I had the Voodoo Doll and Dirty Old Bastard doughnuts, though I would recommend just having one. You could either bring the others home or share with someone else. The Voodoo Doll is dressed like a little ghost, covered in thick frosting and filled with raspberry jelly. The Dirty Old Bastard (ha!) is covered in chocolate and peanut butter drizzle, with oreo/chocolate cookie pieces on it. Even though they are so famous and there was a considerable line on the Friday afternoon I went (I waited about 15 minutes), the doughnuts did not taste that fresh. They probably make them in huge quantities.
Pro tip: They take only cash, so bring enough. They have an ATM, and some funny t-shirts for sale as well. If you visit on the weekend, be prepared to wait in line for 15 minutes to an hour.
Everything at the Saturday Market
The trick is to find the places that have lines. Of course. Try the elephant ears, at the very least. I ate a delicious gyro, and stuffed myself with curly fries. I regret not having another day to go and try some of the other desserts!
All the food trucks
Portland is known for some of its food trucks – and even some restaurants that taste like food trucks! It wouldn’t be a Portland Bucket List with them! You can taste all kinds of ethnic foods – Tibetan, Salvadorian, Moroccan, Middle Eastern, and more common Chinese or Mexican – or classic hamburgers and fries. Yum!
Visiting Portland soon and want to Pin this for later?