Food carts, artisanal doughnuts, the largest independent bookstore in the world, and craft breweries (craft everything, really). Those are just a few of the things to do in Portland that will climb to the top of your bucket list.
Often overshadowed by its neighbor a few hours north, Portland is quickly climbing the list of the best cities in the country to live and visit. There are many things that make Portland special, but as a visitor, there are really three that stand out.
First is that Portland is a highly underrated food city… but not for long (there are at least three Netflix food series that have done an episode on Portland in the past few years). The food scene is interesting, diverse, and surprisingly affordable. Indulging in the local food is one of the top things to do in Portland and once you sink your teeth into the delicacies you’ll understand why.
Second is the incredible green spaces within Portland’s city limits. As a visitor, you’re probably only going to make it to one or two on your first trip – most likely Washington Park and Forest Park – but you’ll get a taste of the greenery that exists within Oregon’s biggest city.
Last is the sheer natural beauty within 90 minutes of Portland. Whether you want surreal alpine vistas or stunning coastal beauty, you’ll find that both are easily accessible from the city (plus too many waterfalls to count!).
There are very few places in the world where you’ll have access to both the beach and the mountains within 90 minutes, and Portland is one of them. You can see why the coast is one of the iconic things to do in Portland.
In this Portland city guide, we’ll go through the things you need to know to plan your first trip to Portland – how to get to Portland, where to stay while you’re in town, and five things you shouldn’t miss on your first trip to the city.
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Table of Contents
How To Get To Portland, Oregon
Getting to Portland from anywhere else in the United States is relatively simple. Portland International Airport, colloquially known as “PDX,” is just a 15 minute drive away from downtown Portland, making it one of the closest airports to an urban center in the country.
Alaska Airlines is the main airline, and there are direct flights to most major cities across the country (though you may have to make a connection, depending on where you’re coming from).
In other cities like Seattle or San Francisco, you can expect to spend almost an hour getting from the airport into the city. In Portland, it’s 30 minutes or less.
If you’re coming from up north – Vancouver or Seattle – you can hop on Amtrak and take the Amtrak Cascades line, which covers the stretch between Seattle and Portland in just under three hours (about the same amount of time as driving).
A Crash Course In Portland’s Geography
Before we jump into this Portland city guide, let’s take a second to cover Portland’s geography. It will give you an idea of how to tackle all the amazing things to do in Portland without wasting too much time.
The city is divided into quadrants, and the most important divide to consider is the Willamette River (pronounced “Will-am-it”) that runs down the center, dividing the more commercial westside, with its high rises and the downtown core, from the more residential eastside.
The contrast between the westside and the eastside is the main difference to keep in mind as you’re planning your trip.
A lot of tourists spend their entire trip exploring the west side of the river, never escaping across one of Portland’s many bridges to experience the more low-key, hip eastern end of the city. It is one of the intriguing things to do in Portland and highly recommended if you want to escape the crowds of tourists.
While downtown Portland and Washington Park – two highlights on the west side of the river – are great, the city really gets its offbeat, “weird” reputation from the east side of the river. If you’re interested in seeing the more interesting side of Portland, make sure to make it east of the river at some point.
Now that you have a very high-level idea of the city’s layout relative to the river, we can jump into how to plan an amazing trip.
The Best Places to Stay In Portland
The first question you’ll want to answer when you’re deciding where to stay in Portland is how long you’ll be in town for.
If you’ve got a short trip – like a weekend in Portland – it makes sense to stay as central as possible to minimize travel time between places. This will ensure that you can cover all the things to do in Portland without wasting time in transit.
To maximize your time exploring Portland, you’ll want to stay in either Downtown Portland or the adjacent Pearl District.
Downtown Portland is where you’ll find the majority of the city’s hotels, and staying here puts you right in the middle of all the action.
Within 5-10 minutes of your door, you’ll have Powell’s City of Books, some of Portland’s best food and drinks, and public transit connections to get to other parts of the city.
If you want a very “Portland” experience, stay at the Ace Hotel, which is right in the middle of all the action and is a true hipster classic. Otherwise.
The Pearl District is adjacent to downtown, and is a formerly industrial part of the city, full of brick warehouses, that has been transformed into one of the city’s more upscale neighborhoods.
There are a few solid hotels here, like the hip Canopy by Hilton, and the surprisingly nice Hampton Inn and Suites.
If you’ve got three or more days in Portland, you can start to think about staying on the east side of the river, which is where Portland gets its reputation for being weird and offbeat from. You’ll trade convenience – it’s significantly harder to get around – for charm and proximity to Portland’s best food and drinks.
For a unique stay, look at Tiny Digs, a collection of tiny houses that is a block from NE 28th Avenue, where you’ll find some of the best places to eat in Portland (don’t miss the tortas at Güero and the mochi donuts at Mikiko). If you’re on a budget, look at Lolo Pass, which is a hotel/hostel hybrid.
The other option on this side of the river is to find a cool Airbnb to stay at – we’d look at Southeast Portland near Hawthorne Blvd or Division St, and in the Alberta Arts District.
Things to Do in Portland
There are many ways to explore Portland. One of the popular way is to book a city highlight tour. It will take you through most of the important locations in the city. Alternatively you can wander through the city at your own pace and time.
Here are some of the things to do in Portland that you really shouldn’t miss while you’re in town.
1. Eat At A Food Cart (or Three)
Catching a bite at the food trucks is one of the best things to do in Portland.
Portland’s food scene is one of the best in the country, and part of the reason behind that is the distinct culture around food carts that has been incubated here.
Many of Portland’s best restaurants started as a food cart, which is a great example of how food carts have created more opportunities for low-cost innovation in Portland, leading to a more diverse and interesting food scene.
Over your time in Portland, you should definitely plan on eating at a food cart, which is a quintessential Portland experience.
There are a nearly unlimited number of food cart pods – collections of food carts, often with a section of shared seating and sometimes a bar – to choose from in Portland, but the best options are the Prost! Marketplace on Mississippi Avenue in Northeast Portland, where you’ll find highly acclaimed Texas-style barbecue at Matt’s BBQ and Indian food with a Pacific Northwest twist at DesiPDX (get the cardamom chai chicken).
Two other good options, which happen to be a few blocks away from each other, are Hawthorne Asylum and Cartopia, both in southeast Portland. Eating at a food cart is definitely one of the things to do in Portland that has to be on your bucket list if you are a foodie.
Alternatively you can also book a culinary tour. It is a great way to explore the local cuisine.
2. Explore Washington Park
If you are looking for green spaces in the city, then one of the things to do in Portland that you will love is the Washington Park.
In a city full of incredible green spaces like Portland, Washington Park is the crown jewel (though massive Forest Park is a close second).
Washington Park deserves the top honor for the International Rose Test Garden alone. Portland, often referred to as the City of Roses, is home to a couple of different rose gardens (including Peninsula Park, the oldest in the city), but the rose garden in Washington Park is the most impressive, with 10,000 roses on display.
It’s particularly impressive between the late spring and early fall, when the multi-colored roses are in various stages of bloom.
In addition to the rose garden, there are a few other things to see in Washington Park. Hoyt Arboretum is definitely worth a stop (don’t miss the Redwood Deck) for its diverse collection of trees from all over the world. You’ll also find the Oregon Zoo and the Portland Japanese Garden in Washington Park.
The park is connected with downtown Portland by the MAX, Portland’s Light Rail.
With limited time, prioritize the Rose Garden and Hoyt Arboretum, and save the Zoo and Japanese Garden for a later visit.
3. Peruse the Shelves at Powell’s City of Books
Powell’s City of Books is the largest independent bookstore in the world. With thousands of books spread across three stories, there’s truly something for everyone. You could easily spend a few hours browsing the shelves to find your next read, just remember that you’ll have to carry the books you buy home with you (so pack an extra suitcase?).
4. Get Over to the East Side of the River
Looking for things to do in Portland without the crowds? Head over to the east side of the river.
Downtown Portland and Washington Park are great, but you have to venture east of the river to understand what really makes Portland special.
The eastside is more residential than the downtown core that takes up most of the real estate west of the river, but the residential blocks are broken up by a series of streets lined with shops, bars, and restaurants that make it a very interesting place to spend some time.
We’d divide the east side of the river into two sections – southeast Portland, and northeast Portland.
In Southeast Portland, the two best stretches are Hawthorne Blvd and Division Street. Hawthorne leans a little more bohemian, with the highest concentration of vintage stores in the city, while Division leans a little more modern and trendy. Both are packed with great places to eat, drink, and shop.
On Hawthorne, go to Fried Egg I’m in Love (which started as a food cart) for amazing breakfast sandwiches with creative names.
On Division, head to Lauretta Jean’s for scrumptious pies, Salt & Straw for the handmade Portland ice cream that has been exported all over the country, and Blue Star Donuts for Portland’s original $5 artisanal doughnut.
You can also take a Portland doughnut tour! Its an epic way to enjoy the different doughnuts.
Northeast Portland is a little more of a trek, but it’s well worth the journey for the cornucopia of food, drinks, and shopping that awaits you. The two stretches to know here are Alberta Street and Mississippi Avenue.
Mississippi is a great place to spend an afternoon and evening eating and drinking your heart out. Start with lunch at a food cart at Prost! Marketplace, walk south down Mississippi and head to one of the two local breweries here – Stormbreaker or Ecliptic – and finish off your evening with pizza at Lovely’s Fifty Fifty and a nightcap next door at Interurban.
Alberta is probably a better morning destination, although that’s not to say it’s not great at other times of day. Go to Proud Mary, which hails from the coffee capital of the world, Melbourne, Australia, for some of the best coffee in Portland, and then grab brunch at either Tin Shed Garden Cafe or Pine State Biscuits.
There are, of course, plenty of other places to eat, drink, and explore east of the river that aren’t included in this relatively small section. With all the delicious food out there it isn’t a wonder that it ranks high on everyone’s list of things to do in Portland!
5. Hike Up to Pittock Mansion
Hiking up to the Witch’s castle is one of the cool things to do in Portland.
The hike from Lower Macleay Park up to Pittock Mansion is one of the best hikes in Portland. You’ll start from the trailhead at Lower Macleay park and follow a babbling creek through the forest, passing the atmospheric Witch’s Castle (which isn’t, in fact, a castle, but an abandoned park building), and climb up to Pittock Mansion.
Pittock Mansion was built by the owner of the Oregonian, the local daily newspaper, in the early 1900s, and has a commanding view of the city from its grounds. You can go inside and tour the mansion, but it’s not a particularly interesting or groundbreaking tour, and the hike and walk around the grounds is probably a better use of your time.
You can either hike the trail one-way, taking a rideshare to and from the trailhead/mansion, or park at the trailhead and do it as an out-and-back. The scenic hike is a highly recommended item on our things to do in Portland list.
About The Author
Matt Hansen is a travel writer from the Pacific Northwest who has fallen head-over-heels in love with the state of Oregon..
He grew up in the Seattle area, and has since migrated south to Portland, Oregon, which is the city he now calls home. He and his wife, Alysha, are the team behind Oregon Obsessed, a travel site dedicated to the beautiful state of Oregon.
They write detailed travel guides to help readers discover the best of Oregon, with a focus on exploring both Portland and Oregon’s incredible diversity of natural beauty.