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A local’s guide to visiting Portland, Oregon

Portland Oregon sign

Now that I’ve officially lived in Portland for more than a year, I thought it was high time to put together a guide to the city. While I definitely don’t claim to have finished exploring—my list is still a mile long—that doesn’t mean I don’t have tons of recommendations and tips saved up! I hope you can make use of this guide when visiting Portland and that it helps you fall as in love with the city as I have (as cheesy as that sounds 🤓)!

A LOCAL’S GUIDE TO VISITING PORTLAND, OREGON

GETTING TO PORTLAND

FLYING TO PORTLAND

You should have no problem flying to Portland, as it’s serviced by every major U.S. carrier (United, Delta, Alaska, American and Southwest all have decent presences there). Coming from the East Coast, though, costs can be steep. If you have access to points and miles, I recommend looking for Alaska flights and transferring points to British Airways to book (you’ll have to do this over the phone, but it’s definitely worth the quick call).

If you do fly in and out of PDX, leave a few minutes to enjoy the airport itself. That may sound ridiculous to some flyers, but it’s genuinely my favorite airport in the world. Priority Pass holders who gained their access through a Chase credit card should check out Capers Cafe Le Bar and Westward Whiskey, where your restaurant credit will get you $28 off your bill.

VISITING PORTLAND BY CAR/TRAIN

Portland is also easily accessible from Seattle by car/Amtrak, with each of those options clocking in at under 3 hours. However, I highly recommend not trying to cram the two cities into one trip unless you have more than a week. The reason is simply that there’s so much to see in day trip range from each of them (Seattle has Mt. Rainier National Park, the Olympic Peninsula and the San Juan Islands all within easy driving range, and these are just a few day trip options from Portland), meaning you could easily build a 5-7 day trip around each city.

Portland Oregon skyline

GETTING AROUND PORTLAND

Portland does have public transportation, but it leaves something to be desired. I haven’t found the light rail and street car lines to be particularly useful, and since you’ll likely want to explore all four quadrants of the city, I highly recommend using a car. While there’s no shortage of ride share options, if you want to venture outside the city (and you should—see below!), you may want your own wheels.

On the bright side, if you do decide to rent a car, know that traffic is usually extremely manageable, as is parking. I rented a car on my first visit to the city and found that no matter where I was going, the ride always seemed to be no more than 10-12 minutes.

WHEN TO VISIT PORTLAND

Portland has two main weather types: gray and rainy, and absolutely beautiful. Weather patterns have sadly been changing over the last few years because of global warming, but generally speaking, the rainy season begins in November and the sun may not begin to reliably come out until late June. My first year in the city was unusually dry, and we had a lot of beautiful sunny days beginning in the spring, but for the best chance of dry weather, I’d aim for a visit in July, August or September. You’ll find blue skies and really moderate summer temperatures; it only gets what I would call seriously hot a few times per year, and even then, the humidity is low enough that it’s not too uncomfortable.

No matter when you’re visiting, though, know that weather can change rapidly throughout the day. Don’t assume that an entire day is lost to rain or gloom, or even that rain will prevent you from doing outdoor activities. Half the time the rain is more like mist, and it’s almost always intermittent. You’ll also see a lot of days that start out cloudy and wind up gorgeous by the afternoon. In other words, pack a rain jacket no matter when you’re coming, but as long as you’ve got that, you should be fine to visit during any time of year.

Willamette River

WHERE TO STAY IN PORTLAND

Portland is divided into five main areas—Northwest, Southwest, Northeast, Southeast and North Portland. The Willamette River divides the east and west sides of the city, and each side has its own character. The east side is definitely the more “Portlandia” side of the two, with eclectic shops and independent businesses, street art and a more residential feel (many people will refer to it as more “authentically Portland”). The west side, meanwhile, is home to downtown and has a distinctly more urban feel, as well as beautiful historic architecture (think old red-brick warehouse buildings that now house shops and restaurants).

Many people will recommend getting an Airbnb on the east side for a true Portland experience, especially since Airbnbs are so cheap. If you want to go that route, look to stay near NE Alberta, NE Mississippi, SE Hawthorne or SE Division, all of which are main drags with lots of shops and places to eat.

If you’ve ever visited this blog before, though, you probably know Airbnb is not really my style 😛There are so many hip, beautiful and affordable hotels on the west side that I can’t help but recommend going that route. Plus, downtown is extremely walkable, meaning you’ll only have to take a car to visit the east side and/or go on excursions outside the city. I’m extremely biased as a resident of the west side, but I just adore it. And rest assured that no matter which side you stay on, you’ll still find plenty of breweries, food trucks, mountain views and the other attributes Portland is known for.

PORTLAND HOTELS (POINTS OPTIONS)

Here are a few of my favorite hotels on the west side, starting with a couple options bookable with points:

The Porter Portland – It may come as no surprise that my go-to is a member of Hilton’s Curio Collection (along with many others I’ve featured on the blog, including here, here and here!). I stayed at the Porter on my first night in the city and loved its comfortable rooms, streamlined decor and city views. Bonus: You can use Hilton Honors points for a free night!

The Hi-Lo Hotel – This is another points option, this time from Marriott’s Autograph Collection. Its spaces are beautiful, its location is unbeatable (walking distance from nearly everything you’d want to do on the west side), and it has a Northwest-inspired restaurant on the ground floor. What more could you ask for?

For more info on how to book these hotels for free using points, check out the 52 Cities free resource library. You can also register to join me on an upcoming masterclass!

flowers
Hi-Lo Hotel bed

PORTLAND HOTELS (NON-POINTS OPTIONS)

The Woodlark – I haven’t personally stayed at The Woodlark, but friends who have stayed there gave it rave reviews. I also spend a lot of time on its ground floor, home to a stunningly beautiful location of Good Coffee (see below!) and one of my favorite cocktail bars in Portland, Abigail Hall. While it’s not part of a major hotel chain, you can book a room for free using the Chase travel portal or by using points from a card such as the Capital One Venture (same goes for the next two hotels!).

The Hoxton – Once again, I have never stayed at The Hoxton, but I spend tons of time at its eating and drinking establishments! Like other Hoxtons, it’s super hip and well-decorated. Unlike other Hoxtons, it boasts THE best rooftop taco place I have ever been to (Tope might be my favorite place to eat in the entire city—get the spicy margarita and the queso fundido!). I also love the unnamed speakeasy downstairs. One thing to note: The Hoxton is not located on the prettiest or best-maintained block of the city, which might make some people feel uncomfortable. Again, I go all the time and don’t feel unsafe there, but just putting it out there.

Ace Hotel – The Ace is another hotel I haven’t personally stayed in, but I’m familiar with the brand through its locations in other cities and I can only imagine the Portland location lives up to the same standard. The chain actually originated in the Pacific Northwest, and Portland was its second location! Speaking of location, the Ace might win for best-located on this list (which is saying something). It’s in a nice area that couldn’t be more convenient to popular areas of downtown, including the Pearl District and Pioneer Courthouse Square.

Pine needles

THINGS TO DO WHEN VISITING PORTLAND

NATURE ACTIVITIES

International Rose Test Garden – They don’t call it the City of Roses for nothing. Portland is home to the oldest official continuously operated public rose test garden in the country, and it is spectacular when in bloom (visit over the summer for more than 10,000 roses!). This garden is probably the biggest must-do in the city, and the views from its lawn aren’t half-bad, either.

Forest Park – Want to do some hiking without leaving city limits? You’re in luck. Head to Forest Park, which boasts more than 80 miles of trails and roads within the 5,200 acres that make it one of the country’s largest urban forests. You’ll find lush foliage, total serenity and, once again, great views.

Mt. Tabor – Mt. Tabor is actually an extinct volcano, and it’s one that’s home to a public park that dates back a century. Bring a picnic, explore its hiking trails and reservoirs, watch a sunset or just enjoy the 360-degree views this 191-acre park has to offer.

Cathedral Park – Yes, Portland has a lot of parks. But before you draw the cutoff line, consider Cathedral Park, which sits below the St. Johns Bridge. Set along the banks of the Willamette River, the park gets its name from the bridge’s footings, which tower above like vaults in a cathedral. It’s a special sight, especially for those interested in engineering or architecture—and it’s a great place to get a look at the the most iconic bridge in Bridgetown.

St. Johns Bridge

URBAN ACTIVITIES

Alberta Arts District – This Northeast neighborhood is home to lots of eclectic independent shops and businesses, as well as tons of great places to east and plenty of street art. Strolling up and down NE Alberta is a great way to get a sense of that part of Portland, and if you pair your exploration with brunch, you can easily fill a morning there.

Shop hop on SE Hawthorne and SE Division – These two thoroughfares each offer a collection of quirky boutiques, cafés and more, and like NE Alberta, they’re great places to explore. Division in particular is a great place to eat (it’s home to Ava Gene’s, one of my favorites—see below!), so plan your visit around lunch or dinner time.

Powell’s City of Books“City of Books” may sound like an exaggeration here, but step into Powell’s, and you’ll get it. It’s the largest used and new bookstore in the world, per its website, and it takes up an entire city block in Portland’s buzzing Pearl District. Inside are about one million books, separated by theme into nine color-coded rooms and more than 3,500 sections that span every possible interest. And there’s more than just books, too! It’s a great place to browse cards, gifts and more.

VIEWS

Portland Aerial Tram – Given its utility as a mode of transportation between Portland’s South Waterfront and the Oregon Health & Science University campus, I’m guessing the Portland Aerial Tram sees many more commuters than tourists. But that doesn’t mean you shouldn’t add it to your list. It’s a short trip up and back, and it provides breathtaking views of the city and its surroundings. Going back during sunrise or sunset—and/or when the mountains are out—is high on my list.

Portland Saturday Market – I’m going to be honest here—I don’t really like the Portland Saturday Market for shopping or eating. Why am I recommending it, then? I love its location along the Willamette, and it’s totally worth it to go for a stroll through the area and do a quick browse while enjoying the riverfront views.

Pittock Mansion – For yet another stunning skyline viewpoint and a great slice of Portland history, head up to Pittock Mansion, a historic house museum. Built in 1914, the house-n0w-museum tracks Portland’s journey from pioneer town to industrialized city through the lens of a local family that helped shape it. Even if you don’t pay to go inside or do the tour (I haven’t), there are signs around the outside of the property and you can stroll around and enjoy the views and garden.

Pittock Mansion
Pittock Mansion

THINGS TO DO OUTSIDE OF PORTLAND

WEST OF PORTLAND

Columbia River Gorge – The Gorge is just outside the city, and you can get amazing views just 30 minutes from Portland. If your time is limited, Multnomah Falls makes a great destination. If you have a whole day, you can do a hike (Angels Rest is a favorite of mine) and then head to Hood River, a little town about an hour away from Portland that’s full of breweries and mountain views (in the warmer months, you can also visit pick-your-own fruit and flower farms nearby).

Mt. Hood – There are lots of great hikes out this way too with AMAZING scenery. I highly recommend the Tom, Dick and Harry Mountain Trail, which takes a few hours but boasts epic views and isn’t too difficult to hike. Timberline Lodge is a great place to get food or drinks after hiking. Mt. Hood is also a ski area and I’ve heard only good things about it, although as a non-skiier myself, I can’t say much more than that.

Mt. Hood

EAST OF PORTLAND

Willamette Valley (a.k.a. Oregon wine country) – Clustered around the towns of Dundee and McMinville are hundreds of top-notch wineries boasting beautiful scenery and the region’s signature Pinot Noir. Make sure to make tasting reservations at wineries before you go, and eat beforehand as they don’t all have food! We always stop at Babica Hen Cafe in Dundee before hitting the wineries. While I have barely scratched the surface of the Willamette Valley and have so many more wineries to try, I’ve so far really enjoyed visits to Soter Vineyards and Eminent Domaine.

Canon Beach/the Oregon coast – Canon Beach is another option not too far from the city that makes a really fun day trip. The water there is too cold for swimming, but the rock formations by the beach are really beautiful and you can spend hours exploring tidepools full of little crabs and other critters. The town of Canon Beach itself is cute, too, and you’ll find tons of places for fudge/candy/ice cream, souvenirs, and other beach-town staples. Definitely stop at Ecola State Park on the way to or from Portland for INCREDIBLE views right from the parking lot.

Haystack Rock

For more Portland day trip ideas, check out this post!

WHERE TO EAT IN PORTLAND

SIT-DOWN – RESERVATIONS

Ava Gene’s – Ava Gene’s is a staple for modern Italian food on SE Division, and simply put, everything there is good. This is our go-to for special occasions or “our parents are in town” dinners, and it’s an equally fun place to get a little dressed up and pop in for a cocktail at the bar. You will definitely need a reservation, so plan ahead!

Tusk – Tusk is a sister restaurant to Ava Gene’s, but instead of Italian, it does Mediterranean small plates. They key here is to order a bunch of things and share, whether it’s for dinner or brunch (both are worth a try if you’re local). The space is light and airy and there’s a tented, heated outdoor patio, too.

Kachka – If you don’t know a lot about Russian food, don’t worry—you’ll definitely find something to love at Kachka. It offers a modern take on Russian classics, and everything I’ve ever tried there has been amazing. Go hard on the dumplings (pelmeni); the cheese and sour cherry varieties are both out of this world.

SIT-DOWN – MOSTLY WALK-IN

Tope – This is the aforementioned rooftop taco bar at the Hoxton, and my love for it knows no bounds. It’s a dream for interior design lovers, taco lovers, or just those who enjoy sitting outside on a summer night enjoying sunset views of the mountains. It does get very busy (and doesn’t take reservations), so plan to grab a pitcher of spicy margaritas and wait a little bit.

Afuri Izakaya – This popular Japanese ramen chain (that I first visited in Tokyo!) chose Portland as its first location outside its home country, citing “soft water from a pure source within close proximity” and the “bounty” of local farms and producers as two big factors in the decision. Simply put, the ramen here kicks ass. It’s another place where you can expect to wait; put your name down and consider grabbing a drink nearby.

Tasty & Alder – Tasty & Alder is not one of my personal favorites (I personally prefer sister restaurant Mediterranean Exploration Company just because the menu is more vegetarian-friendly), but I would be remiss not to include it. It’s one of Portland’s best-known dining destinations, and for good reason. Brunch is really the famous meal here, but dinner is impressive and much less crowded.

Ava Gene's
Ava Gene's

CASUAL

Proud Mary – Proud Mary is an Australian cafe, and if that doesn’t mean anything to you, let me tell you—it’s a very, very good thing. Its menu is full of healthy yet amazing dishes that you can easily customize to fit any dietary restriction or preference you may have, and avocado is an optional add-on to literally everything. I definitely recommend the side of potato hash, too.

Lardo/Bunk Sandwiches – It may be a bit unfair to group these two together, as each has its own distinct menu and loyal following. But they’re both popular Portland sandwich chains, and they’re both great places to grab something quick amid an afternoon of exploring (or take something to go for a park picnic).

Sizzle Pie – My pick for pizza. Don’t worry if you’re dairy-free, gluten-free, vegan or all of the above—Sizzle Pie has you covered. This is Portland, after all.

DESSERT

Blue Star Donuts – Okay, here is my first dessert hot take. Doughnuts were definitely “a thing” in Portland when I visited five years ago, but now that every major city has artisanal doughnut shops, I don’t necessarily think you need to seek them out here. If you still want to give them a try, I definitely prefer Blue Star to Voodoo.

Cloud City Ice Cream – Second dessert hot take. I hate Salt & Straw. Again, if you feel like you need to try it, be my guest. But then head to Cloud City to try PHENOMENAL ice cream that has flavors that are interesting without being over the top or straight-up grotesque (I have seen bacon & egg ice cream in Salt & Straw before and nobody is going to convince me that that is okay).

Beer

WHERE TO DRINK IN PORTLAND

COCKTAILS

Hale Pele – The tiki bar to end all tiki bars. Seriously, this place is one of the premier tiki bars in the country (or so I’ve heard, and I believe it). The drinks are phenomenal, the sound/mist effects are on-point, and the whole place has a super Portland air about it. Expect to wait, no matter what time you go.

Abigail Hall – Continue past Good Coffee in the lobby of The Woodlark and you’ll find Abigail Hall, a cocktail bar bedecked in floral wallpaper that was practically made for Instagram. I love the creative cocktails here (and that the bar is named for Abigail Scott Duniway, Oregon’s “Mother of Equal Suffrage”).

Pepe Le Moko – If you’re feeling dark and moody—or like you just want to go somewhere that does the classics really, really well—look no further than Pepe Le Moko. This intimate downtown spot inside the Ace Hotel hides behind a facade of pantry items; look for the door that leads downstairs.

Vault Cocktail Lounge – For a super chill bar with space to sit and room to hear yourself talk—as well as grade-A cocktails— head to Vault in the Pearl District. It’s my go-to when I don’t feel like battling crowds to get in somewhere scene-y, and by the time you read this, there’s a high likelihood I’ll have turned into a regular.

Basement Bar – This is the speakeasy in the basement of The Hoxton that I wrote about above. While it takes a little work to find the door, all you have to do is ask around and you should get pointed in the right direction. It’s worth the search; you’ll end up in a cozy space where the bartenders are willing to make up a cocktail for you based on your tastes.

WINE AND BEER

Oui! Wine Bar + Restaurant at the Southeast Wine Collective – This place really has it all: interesting yet approachable wines, amazing food, friendly servers. Oh, and did I mention it couldn’t be cuter? Get a flight and some small plates to share and you’ll be set for the evening. Just note the hours; Sunday and Monday, it closes early at 9 p.m.

Breweries – Portland is famous for its brewery scene, and you could hit 10 per day during your trip and probably not run out. From some larger ones you may have heard of (Rogue, Deschutes, Widmer Brothers) to smaller, local spots that don’t distribute nationally, your options are nearly endless. Make sure to try at least one, even if you’re not a “beer person!”

COFFEE

Good Coffee – I am admittedly a little biased by Good’s gorgeous decor and seasonal latte flavors (not exactly a coffee purist over here), but as far as I can tell and have verified with others, the coffee itself is pretty killer. There are four locations around town, including the Woodlark lobby location I mentioned above.

Coava Coffee – Coava roasts its own beans, and you’ll find them used in cafes all around town. It also has four of its own locations in Portland (and one in San Diego!), each with its own character. The coffee is really stellar—definitely give it a try.

Upper Left Roasters – Upper Left has good coffee to be sure, but it really won me over with its homemade macadamia milk and its selection of toasts (I’m not kidding—they are so good). Visit the Ladd’s Addition location for more room to spread out and and some Insta-perfect interior design.

Sunrise

STILL ON MY LIST

Multnomah Whiskey Library MWL’s own website refers to its collection of distilled spirits as “exhaustive,” which gives you a pretty good picture of what’s happening over there. It’s somewhat hard to get into and I really don’t like to drink straight whiskey, so I haven’t prioritized going, but I’ve heard there’s nothing like it and definitely want to experience it at some point! Whiskey lovers—go and tell me how it is?

Portland Japanese Garden – A visit to the Portland Japanese Garden can easily combined with a trip to the International Rose Test Garden given their proximity to one another, but unlike the rose garden, the Japanese garden charges admission. Still, it’s supposed to be well worth the price, given its eight separate garden spaces. You can also watch authentic Japanese tea ceremony presentations, which I’ve heard are very cool!

Woodblock Chocolate Manufactory – As a chocolate fiend, I honestly can’t believe I haven’t done this yet. You can watch chocolate being made while dining in a chocolate cafe. Dream activity.

Swiss Hibiscus – This restaurant is at the top of my list and I think the presence of Rösti Valaisanne on the menu explains why.

For more on Portland, check out this guide to the best day trips from the city or this weekend itinerary for first-timers! Need a longer itinerary for Portland? This five-day plan works in day trips so you can see the best of the region.

Hope this Portland city guide is helpful! What other questions do you have about visiting Portland? Let me know in the comments! >>

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Visiting Portland Oregon
Visiting Portland Oregon
Visiting Portland Oregon

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Carly

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2 Comments

  1. Reply

    Kellie

    June 22, 2020

    I was born and raised here in Portland and live in SE. I think you did a WONDERFUL job with this post. I see so many blog posts from visitors that feature Voodoo donuts because they are iconic to Portland despite the fact that they basically have Safeway donuts with cereal on them. Blue Star hands down has the best doughnuts. I agree on Sizzle Pie for any kind of pizza vegan gf etc. Yes our Saturday Market is so overrated, but fun for a walk along the river! FINALLY a blogger that hates Salt & Straw (I do too). Cloud City Ice Cream is the best ice cream in the city with the largest selection of vegan ice cream. I would like to add Burgerville and Tillamook are classic and worthy of a visit. Rockaway beach is by Tillamook and the rock formations are worth visiting.

    • Reply

      Carly

      June 26, 2020

      Thank you so much, Kellie! That means so much coming from a local! I’m so glad we agree on Salt & Straw, haha – Cloud City is so far superior 🙂 I will definitely add Burgerville and Tillamook to my list. Thanks again!

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