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3 Days in Portland: How to Spend a Long Weekend in Portland

So you’ve got a long weekend in Portland, Oregon. Lucky you! Whatever your traveling style, Portland has got something for you. For outdoor adventure lovers there’s more than enough to keep your body moving both in the city and nearby.

For the foodies and beer connoisseurs, you can jump from neighborhood to neighborhood eating and drinking your way across town. Chances are, you’re looking for a balance of both in which case we’ve got the Portland city guide for you! 

I’d like to claim I’m a Portland native, but alas, my family moved here when I was two so I can’t honestly take that title.

However, aside from a stint in Cali in my early 20’s, I’ve lived here my whole life and in all five quadrants, and have been asked by more than a few visiting friends, “What should I do when I’m in town?”

So what should you do? I got you covered, fam. Read on to learn exactly how to spend 3 days in Portland according to, well, me. 

Wondering where to stay in Portland? Check out our guide to where to stay in Portland, with the 8 best areas to stay, pros and cons for each, and suggestions on places to base yourself.

Disclaimer: Some of the links in this post, like hotel and vacation rental links, are affiliate links, meaning at no additional cost to you we make a little bit of money if you click through and book. That being said, we would absolutely never recommend something to you that we don’t stand behind 100%.

3 Days in Portland: A Complete Long Weekend in Portland Itinerary

For the purposes of this Portland itinerary, we’re going to assume you arrive on Thursday evening, and have a full three days for exploring the city before you catch your flight home.

Thursday Night: Arriving & Dinner and Drinks 

As I stated earlier, the Portland Airport is one of the best in the country, and you can count on a smooth experience getting your luggage and finding transportation. With that, you’ll have time to make it to your hotel, freshen up, and still make it out for your first dinner in town, the first step of your jam packed 3 day Portland itinerary.

Downtown: There are plenty of dinner options right downtown, but they get busy, so try to make a reservation or have your hotel concierge make one for you. 

  • If you like Chinese food, you’ve got to try the soup dumplings at Duck House

  • If you don’t want a lot of fuss on your first night in town, try Kalé for quick, Japanese comfort food, Sizzle Pie for an easy and delicious slice, or Bless Your Heart Burgers for a classic cheeseburger and fries. 

Before heading back to your hotel stop by Momo’s for an easy drink in a slightly-divey bar, or a subdued, classy experience at Multnomah Whiskey Library

The Pearl: I swear there’s a new, incredible restaurant popping up every week in the Pearl. 

  • If you’re looking to have a fanicer experience go to the Mediterarnian Explorations Company and order the tasting menu. 

  • For a more casual dinner try Piazza Italia (it admittedly doesn’t look like much from the outside, but trust me and trust their housemade pappardelle), or VonEbert for great brews and pub fare. 

For after dinner drinks either sink into a velvet booth with a cocktail at the Pink Rabbit, grab a pint at The Big Legrowlski, or maybe you’re a traveler after my own heart and you prefer a grimy dive in the aptly named Low Brow Bar (where I actually go when I’m in the Pearl).

The Eastside: For a slightly spendier, novel dining experience, you’ve really got to try Kachka. I didn’t know much about Russia food until I went to Katcha and I had so much fun! Everything is so creative and you must try their dumplings.

For something simpler and especially if you’re gluten free or just into really good healthy food, I can’t recommend Harlow strongly enough. The only caveat is they close at 8pm, and don’t really have a “dinner” menu as much as an all-day menu. If you want quick, delicious and lots of options, try one of Portland’s famous food cart pods, Cartopia

If you’re into wine and want a slightly classier (but still not pretentious) spot for food and drink, grab a glass at Ok Omens, or the swanky yet kitschy Gold Dust Meridian.

Friday: The Columbia River Gorge, Brunch, & OMSI

Morning: Take a hike!

This is your best chance to get out for a hike in the nearby Columbia River Gorge and enjoy trails roughly 25% (my own calculation) less crowded than they would be on Saturday or Sunday. It’s still a good idea to leave as early as you can, as trailhead parking tends to fill up around 9 or 10am. Pick up bagels and schmear at Bernsteins on your way out of town. 

A great bang for your buck is the 5 mile Angel’s Rest hike, only about 30 minutes from Portland. If you leave by 8am you’ll get a workout, take in spectacular views, and be back in town for lunch. Another good close-ish option is the 7.5 mile Cape Horn loop on the Washington side.

If you’re interested in hiking, check out our guide to the best hikes in Portland!

Brunch Time!

If you’re staying in town it’s time for the main event in Portland – brunch! Friday should give you a (slightly) shorter wait time, but waiting for a table is all part of the brunch experience. 

I could probably list 100 restaurants here, but instead I’ll give you three: 

  • An old standby for me has always been the Cricket Cafe on Belmont for good food and big portions. 

  • Broder Cafe (they’ve got a couple locations) for Swedish pancakes

  • Hunnymilk for a fun take on brunch where you choose one drink, one savory dish, and one sweet dish and have them served up cafeteria style. Apologies to the 97 other remarkable brunch spots in town. Much love.

Afternoon 

Portland,Oregon,usa.-2016/07/16 : OMSI ,museum of science and industry.

I’ve set up a Friday afternoon for those intrepid souls visiting Portland in the colder and wetter months, and for this I highly recommend OMSI for kids and adults. The Oregon Museum of Science and Industry consistently has the coolest exhibits and every time I go I wonder why I don’t go more often. 

It also puts you close to Pine State Biscuits for a tasty lunch, and while on your way you must, must, must stop and view the city’s best mural located on SE 10th and Division. 

After OMSI, pop over the bridge into downtown and spend the rest of the day at Ground Kontrol, playing over 60 classic arcade games and sharing in Portlanders second favorite rainy day activity, drinking!

Happy Hour Drinks

Before you decide on dinner, I highly recommend hitting up the Portland City Grill for happy hour (don’t bother for dinner – it’s nice, don’t get me wrong, but I actually prefer the bar area) and you can get a classy cocktail and see Portland from the 30th floor of Big Pink (aka the US Bancorp Tower, but everyone just calls it Big Pink). 

Dinner Time!

When I’m traveling to a new city I like to splurge on at least one fancy meal out, but sometimes to really get a feel for the city you want to eat “like a local.” If you took my earlier advice you’re just finishing up your last game of Ms. Pacman and getting hungry. 

For a spendy option, try Andina. Trust me you’ll want to splurge on this Peruvian fare, and I’ve not been disappointed once. Plus, the staff and overall vibe is fun and warm and inviting. Treat yourself to one of their house cocktails. 

A good mid-range option is Breakside Brewery Slabtown, one of my favorite Portland breweries and they’ve got damn good food too. Also fun is Marrakesh – sit on pillows! Watch belly dancers! Eat delicious Moroccan food with your hands! 

Wanna go cheap? Escape from New York Pizza was my favorite as a teenager and is still a favorite today. It’s the gift that keeps on giving. Or try Bibi2Go and as the name suggests, this is only a counter order place, but oh my you’ll get some good bibimbap!

After Dinner Drinks and More

I love the Pope House Lounge and you will too if you’re a fan of bourbon or of Victorian houses turned bars – super chill and cozy. 

Craving dessert? Get a cocktail and a sweet crepe at Le Happy, one of my go-tos for when I want a special place to take friends but don’t want to deal with crowds or waiting. 

Bartini is small but if you can get a seat you’ll be blown away by their . . . you guessed it! Martinis! 

And if it is in fact pouring rain but you’re not ready to call it a night, head over to Cinema 21, one of the oldest movie theaters in Portland that shows independent, foreign, and classic movies. 

Saturday: Markets, Downtown, and the Eastside

Woohoo! Saturday! The sun is shining and it’s a beautiful day in Portland. This morning you’ll start you downtown then make your way across the Willamette River to end your day. 

Morning

Start your morning at the PSU Farmers Market, Portland’s only year round farmers market. Even if you don’t end up buying anything it’s a nice way to start your day and you can grab coffee and breakfast at one of the many hot food carts. 

From there, you can either walk or bike through Portland’s beautiful park blocks (and if you do take a quick stop at Pioneer Courthouse Square to experience the echo chamber located on the NW corner. It will only take a minute to do, and trust me – it’s cool.) Or, you can jump on the streetcar and head over to your next destination, Powell’s City of Books. 

Powell’s is the largest new and used book store in the WORLD, so like, you have to go. For a bibliophile, you’ll think you stepped across the pearly gates into heaven and your friends will have to pry you away (after they hunt you down). Even if you’re not a book nut, you’ll still be impressed and I promise you will find something to catch your fancy. 

Afternoon

You’re probably ready for lunch now and you have a choice because I’m taking you down to the waterfront next to visit Portland’s Saturday Market. 

You can either wait to eat down there at one of the many food vendors (I’d always get an elephant ear as a kid but I know that’s kinda stretching it for “lunch”), or you can grab a bite near Powell’s. Lardo is one of my faves in the area and I could eat their pork meatball banh mi every day of my life. Another great option is Boxer Bento with a small but tasty menu.

Onward to the Portland Saturday Market which has been running strong since 1973, and is the oldest continually running arts and crafts market in the US. It’s super fun to walk around and check out the local artisans, watch street performers, and eat yummy food. Afterward you can walk through Waterfront Park which is always bustling on a sunny Saturday. More information here.

A sunny afternoon in Portland is also a great time to ride your bike and see the city. I’d recommend hitting up the Eastbank Esplanade Loop (note that this map takes you across the Hawthorne bridge, but you should go a little farther and cross over on the new Tilikum Crossing, a bridge designated for only public transit and pedestrians.) Or try this lovely 13 mile loop that will take you through Portland’s SE neighborhoods. Or you know, just ride your bike wherever you want!

Evening

After you cross a bridge by foot, bike, or vehicle (the Hawthorne and the Steele are the best for pedestrians) you’ll be ready to eat! 

  • For fancier dinner, I recommend Olympia Provisions for Insta worthy charcuterie boards (also buy some cured meat to go). 

  • For mid-range try Nostrana for a classy Italian meal with a great vibe (also wonderful thin crust pizza!) or Bollywood Theater for Indian street food (I can’t not order the kati roll every time I go). 

  • For cheap and good try Guëro for pozole and tortas (a note from Matt & Alysha: AND MEZCAL!)

Saturday is also a great night to catch a show at one of the city’s numerous music venues. Of course the performers will change, but my favorite venues around the city are Revolution Hall (that also has comedy shows), the Crystal Ballroom (home of the famous “floating floor”), and Mississippi Studios (an intimate venue that books killer acts).

Alternatively you can check out the lineup at Helium Comedy Club and support the city’s thriving stand up comedy scene.

If you’re ready for a drink, pop over to the Mississippi neighborhood and you’ll have your pick of the litter, but my two favorites in that area are Bar Bar with its huge outdoor patio, and Ecliptic Brewery.

Sunday: Forest Park and Pittock Mansion

Morning: Take another hike! 

Portland is home to one of the largest urban forests in the country covering 5,200 acres. The lush Forest Park is a favorite of hikers, walkers, and trail runners, and you really should check it out before leaving town. 

A great way to do this is with this hike. This 5.5 hike starts at Lower Macleay park and steadily climbs up to the victorian-era Pittock Mansion. You can walk the grounds at the Pittock and get killer views of the city, then pop back down the way you came. 

If you don’t have the time to do the whole thing you can easily cut it in half and only go as far as the Audubon Society, then turn around (but not without saying hello to the resident birds, Julio, Aristohpanes, Ruby, and Xena). You’ll also pass the spooky and potentially haunted Witch’s Castle on this hike, a great place for a photo op. 

Afternoon 

I can’t imagine a more idyllic way to spend my last afternoon in Portland than strolling through the Portland Japanese Garden (more information here). Not only will you see meticulously maintained gardens, trees, and walkways, but you’ll also get spectacular views of the city and Mt. Hood as a fitting send off for your travels back home.

Got More Time? Here are More Options to Fill Your Day

The view on a clear day from Powell Butte

There are plenty more hikes in Portland to see the area, move your body, and be one with nature: Council Crest on the west side, and Mt. Tabor, and Powell Butte on the east side are all popular and worthwhile destination..

Explore the city’s parks. Portland has so many spectacular neighborhood parks (make sure to read our guide to parks in Portland to figure out which to explore!), and a lovely way to spend an afternoon is to get some food to go and have a picnic. Some noteworthy spots are Laurelhurst Park, Washington Park (home of the International Rose Test Garden), Cathedral Park (in my very own neighborhood!), and Peninsula Park (more rose gardens!).

A close second to OMSI for my favorite rainy day Portland activities is roller skating at Oaks Park, a Portland mainstay for over 100 years.

Time your visit for festivals: I’ve already mentioned the Winter Lights Festival but will again because it’s JUST THAT COOL. There’s also the Rose Festival in June with parades, a costumed fun-run, and a pop up amusement park on the waterfront; MusicFest NW in August for killer lineups; and a special shout out to the Polish Fest in September for dancing the night away to live polka music.

Cathedral Park in North Portland

Where to Eat & Drink in Portland

Portland is a world-class food city, but not in the same way as New York City or London. It’s far more diverse, both in terms of cuisine, and in terms of price range. You can find a Michelin-star-worthy meal, or eat at a food cart for $5. Portland’s thriving small business economy means that there are options for nearly every budget, style, dietary restriction, and more. 

Eating in Portland

I peppered lots of eating suggestions throughout this itinerary, but here I’ll showcase the places that somehow didn’t fit into my blurbs. These are all places I personally love and patronize and you should too.

Lauretta Jeans – Taking home a pie from Lauretta Jeans is infinitely cooler and tastier than taking home a box of donuts from Voodoo (see below). Sorry not sorry

Matt’s BBQ – This food cart located on Mississippi Ave. frequently sells out before closing so don’t dilly dally to get in on this Texas style bbq.

Nuestra Cocina – A great place for a nice and festive dinner, serving “peasant” style Mexican food.

Pambiche – A small, always busy, always fantastic Cuban eatery.

Reel M’ Inn – If you’re interested in eating the best fried chicken and jojo’s in town at a dive bar next to video poker machines, well then, I like you. And you should visit the Reel M’ Inn tavern. 

Donuts and Ice Cream – I know what you’re thinking, and I’m not gonna say it! In fact I’m gonna tell you NOT to go to Voodoo Donuts. And I’m gonna tell you NOT to go to Salt & Straw. I’ll probably get kicked out of Portland for that. I mean, they’re fine, but the line to get them is forever long and you can get muuuuuuuuch better donuts in Portland (okay Salt & Straw’s ice cream is the bomb, but if you must go here’s my protip: cut to the front of the line – it’s legal – and buy a couple pints to go). My personal favorites are Pips and Nola for donuts, and for ice cream go to Cloud City or Doe (bonus that Doe has donuts too!).

Drinking in Portland

Whether you’re looking for a morning cup of coffee to jumpstart your day, or a nightcap to end it, Portland has you covered. 

Coffee and Tea in Portland

Heart – With three locations in Portland, you’ve got no excuse not to try Heart coffee when you visit. Order a korvapuusti with your cappuccino.

Coava – They’ve got four locations in Portland, but my favorite is their flagship on SE Grand. Grab a drink and take a bag of beans home with you.

Tao of Tea at the Lan Su Garden – When you’re in the Tea Garden it’s easy to forget you’re in the middle of downtown Portland. Sublimely serene and tea brewed to perfection. 

Beer in Portland

Like all food and drink in this town, I’ll inevitably leave some deserving soul out, so I’m again listing my personal favorites.

Upright – Upright specializes in an open fermentation process and their tasting room is hidden away in a basement in the Rose Quarter and is only open on weekends, but you can find them on tap at many local restaurants. One you’ll see a lot (and one of my favorite beers ever) is their Supercool IPA.

Cascade Brewing – A leader in the NW sour beer scene, this is a bustling brewery in the central eastside. Even if you’re not into sour beers (and I didn’t think I was) try it!

Little Beast – A new, small brewery operating out of a house in SE Portland, Little Beast is quickly becoming a sought after spot in the saturated Portland brewing world. Try their Tree Spirit or Dream State.

Not Beer in Portland

Portland Cider Company – Not only do they have great cider, but great food too! And an excellent happy hour.

Noble Rot – On a fourth food rooftop on the eastside, this is the place to be for sunset on a warm fall night for great food, a phenomenal wine selection, and friendly and knowledgeable staff. 

Where to Stay in Portland

Though Portland is a “big city”, it doesn’t actually feel that big on account of the neighborhoody vibe of its burroughs. When visiting (especially if it’s your first time), opt for a centrally located homebase and you’ll have more than enough to do. Here are three areas that will serve you well for a fantastic 3 days in Portland, Oregon.

Downtown Portland

Downtown is the most convenient place to stay with its abundant bars, restaurants, hotels, and access to public transit. Yes, there are more “artsy” and “weird” neighborhoods to stay in, but it’s quite easy to get to those from downtown.

The best places to stay at are the Ace Hotel (pet friendly, but note they don’t have onsite parking) with the fabulous Clyde Common restaurant downstairs, or the Society Hotel offering options for standard rooms or bunk rooms for a cheaper hostel-like stay. 

The Eastside Between Belmont and Division

The eastside of Portland is historically more grungy and offbeat, and while some of that is still true, it’s expanded so much that you can now find a good mix of the newest Portland fads with the old Portland feel. The central eastside is known for its stellar food options, trendy bars, quirky shops, and tree lined neighborhoods. 

The best way to stay on the eastside is to live like a local and grab an Airbnb. This beautiful and airy guesthouse is right on Clinton Street (home to the famous Clinton Street Theater and their 40-years-and-running midnight showing of the Rocky Horror Picture Show). 

Or, you can fully immerse yourself in the art scene by staying in this large studio that’s not for everyone, but maybe you’re not everyone and you actually want a fire hydrant in your bathroom. 

The Pearl District

The Pearl has expanded so fast over the last 10 to 15 years that it’s nearly unrecognizable to this 80’s and 90’s child who knew it only as shady warehouses-turned-art-galleries. Now, it’s uber chic and filled with high-end stores and restaurants and can be really fun if you’re looking for the bustling “city” experience. 

The best part about the Pearl is its location, but finding a place to stay can be tricky, though there are a few good hotel options. 

I’d go with the Canopy by Hilton for the location and nice, well-appointed rooms. Or the retro-feeling Hoxton for affordable yet nice options (which is technically a block outside of the Pearl, but it’s a great location right between the Pearl and downtown). 

The Best Time to Visit Portland

Summer is hands down the best time to visit Portland. With an average summer temperature of 80 degrees it’s hot enough, but not too hot to keep you from enjoying the whole day outside. There are numerous festivals happening every weekend and it’s the best time to view the city’s many rose gardens (you are visiting the City of Roses afterall).

Fall gets second place for visiting Portland. The weather can still be good (especially September and October), and most of the area’s tourist attractions will be less crowded which is a huge plus for this ever-growing, ever-popular city. You usually won’t get as much rain as in the springtime, but bring a raincoat!

I happen to be writing this in spring, and I must admit it’s great! Though the weather can be hit or miss, most of us Portlanders have been hibernating for the past few months so when those first days of sunshine start coming, the city comes alive and people are out in droves soaking it up and there’s just a general feeling of goodwill and gratitude in the air.

I don’t want to detract you from visiting in winter, but you should know what you’re getting into. Portland rarely sees snow, so most winter days are cold and rainy. BUT! The city is still cool and winter is a great time to check out restaurants, bars, museums, and for the hearty you’ll get to explore the region’s hikes without battling for parking spots. If you do travel during winter, I implore you to catch the Portland Winter Light Festival which is one of the coolest things to do in Portland any time of year.

Getting to Portland 

Flying into Portland is a dream. Portland International Airport – lovingly referred to as “PDX” – is consistently ranked one of the best airports in the country, and any time I have to endure another airport I long for the ease and comfort of PDX. 

It’s also not too far from the city center, and depending on where you’re staying, taking public transit can be incredibly convenient.

Getting To and From PDX 

There are three main ways to get from the airport to your accommodations, and when you’re planning a trip to Portland, Oregon where you’re staying and what’s on your itinerary will determine what you choose.

The MAX (Metro Area Express) 

The MAX is a light rail train that’s easy to use, even for non-city dwellers. The red line takes you straight to the airport and is a great option if you’re staying downtown or around the Rose Quarter. Day passes are $5 and are transferable to the busses and streetcars. If you plan on staying in and exploring the city center, this is hands down your best option.

Lyft

Ordering a Lyft is a good option if you’re staying in a non-downtown neighborhood, but still plan on remaining mostly in the city and traveling by foot or bike. The city does have an extensive bus system which is an option, but a Lyft will cost you $20-$30 to get you from the airport to your accommodations, and is an easy way to start your trip.

Rent a Car

Advisable if, a) you’re not staying downtown, b) you want to explore outside of the city like the Columbia River Gorge, or c) you’re visiting in winter. While Portlanders are big on their bikes and their public transit, they still love their Subaru Outbacks to take them up to the mountain for the day.

Getting Around Portland

Should You Rent a Car?

See above for rental car advice. Not gonna lie, it can be nice to have a car sometimes in Portland, even if you’re big on the non-car lifestyle. If this is your first weekend trip to Portland, I’d advise you to stick to spots that are centrally located and easy to get to on foot or bike, or you can splurge on the occasional Lyft. 

The bus system is great, but it’s not great for getting across town in less than an hour and a half. 

If you’re traveling with kids, you may also want a car because when you need to leave, you need to leave. I get it. 

Public Transit

Portland has a very well established transit system (TriMet) that’s easy to use and consists of three main systems: the MAX, buses, and streetcars. 

The MAX is great if you’re mostly downtown or around the Rose Quarter. The buses go everywhere but do take longer unless you’re only traveling a short distance and don’t have to transfer. The streetcars mostly run in a big loop that goes through downtown, across the river then parallel on the east side. 

You can buy one ticket for TriMet that works for all systems, and a day pass will cost you $5. You can either buy a paper ticket at any MAX stop, or buy a Hop Card which is reloadable. The easiest way though is to pay by phone either by downloading the Hop app or paying with Apple, Samsung, or Google Pay. All buses and trains have scanners when you board making fares a breeze.

Biking Around Portland 

Biking is a great way to see the city, and there are a number of options for renting a bike during your visit. Plus, it’ll make you feel like a real local!

Hotel Bikes

More and more hotels (and some Airbnb’s) offer their guests either free or rental bikes with their stay – the Ace HotelJupiter, and Hotel Rose to name a few.

Biketown 

There are benefits to staying in a city besieged with the massive influence of Nike, and their “Biketown” bike stations are definitely one of them. 

These are easy to use and easy to find (they’re bright orange). They currently have over 1,500 bikes in circulation and 180 stations. The Nike bikes are best for short trips since you rent by the hour and have to return them to a Biketown station. 

Bike Shop Rentals

In a place dubbed, “Bike City, USA,” you’d probably guess there’d be plenty of bike shops around and you’d be right. This is a good option if you know you’ll want a bike the whole time you’re here, and you don’t want to stress about finding a station to return it to each time. There are many, but check out Everybody’s Bike Rentals, Pedal Bike Tours, or Cycle Oregon. 


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