Portland, Oregon: The Perfect Weekend Itinerary

3 Days in Portland, Oregon: The Perfect Weekend Itinerary

They say to keep Portland weird, and while it is true that this Oregon city has changed a lot in the past few decades, we think it’s safe to say that Portland is decidedly still weird. Just the way we like it.

But Portland has perfected the things that make it so unique. Its food scene is filled with some of the best restaurants in the country, as well as hole-in-the-wall places that the locals have been in love with for years. Plus, it’s got a happening bar scene, from tons of craft breweries to some of the strangest, most wonderful cocktail lounges you could imagine.

It also takes great pride in being green, literally. With a multitude of parks, beautiful gardens, and hiking and biking trails both inside and nearby the city, Portland is a place to revel in the great outdoors. Assuming it’s not raining, which it does about 164 days per year.

Whenever you plan your trip to Portland, you’re in for a weird and wonderful time. Not sure where to start? We’ve put together a 3-day Portland itinerary to help you see the very best the city has to offer. Stick to this list of top dining spots and attractions, and you’re bound to have an incredible time in the City of Roses.

If you’re still deciding where to stay then make sure to check out our article on the cool and unique hotels in Portland, Oregon!

How to Spend a Weekend in Portland, Oregon

*This itinerary assumes that the first day of your 3-day weekend in Portland is a Friday. Some things on this list are time-sensitive, namely the farmers market and Saturday market, which only occur on Saturdays.

Portland Weekend Itinerary – Day 1

Blue Start Donuts 

3 Days in Portland Itinerary: Blue Start Donuts

We’re going to kick off our 3-day trip to Portland with a controversial pick. While some people would say that you need to get Voodoo Doughnuts whenever you go to Portland, we’re going to steer you toward another doughnut shop with a shorter wait and (arguably) better doughnuts: Blue Star Donuts. They’re less sugary-sweet than Voodoo and come in more unique flavors, like the Blueberry Bourbon Basil or the Matcha Lime Crumble.

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Portland Art Museum 

Portland 3 Day Itinerary Weekend Guide: Portland Art Museum

Fuel up with a hearty doughnut and a cup of coffee, then head out to your first activity of the day. With 240,000 square feet, the Portland Art Museum is the largest art museum and one of the oldest in the country. This museum houses a permanent collection of over 42,000 works of art, but there are limited-time exhibit offerings happening all the time. 

Spend the morning immersed in art. You’ll see work from local artists and world-renowned masters and art that gives you a look into cultures beyond your own. When you’re visiting, be sure to check out PAM CUT to see what’s being screened at their theater. 

For the next activity on the first day of your 3 days in Portland, you have two options. Portland is renowned for its food and beer scene. There are over 70 craft breweries in Portland. If you’re a beer connoisseur, there’s hardly a better place to visit. 

Food or Brewery Tour

3 Days in Portland Weekend Itinerary: Brewery Tour

Portland is also highly bike-friendly, which offers you a unique tour option if you want to see the city’s many breweries. With BrewCycle, you’ll cruise around with up to 14 other riders on a Dutch-inspired pedal-powered vehicle, taking you to sip at four Portland breweries. 

Don’t want to have to pedal to your destinations? Try City Brews Tours instead, where you’ll ride on a bus with other beer fans to explore the area’s breweries. Along the way, you’ll also get a souvenir glass, pretzel necklaces, and a beer journal and tasting guide.

Not much of a drinker or traveling with a few underage visitors? Try a food tour instead. Portland is also known for its diverse cuisine, with everything from some of the best doughnuts in the world to its unique take on pizza. If you’re not doughnut-ed out, there’s always the Underground Donut Tour

But for more options, try a Forktown tour. Forktown operates several food tours around Portland, but you’ll likely want to stick around downtown, so you’re nearby the other attractions on your Portland itinerary.

Next up, you’re grabbing dinner at one of Portland’s most famous institutions: Huber’s Cafe. Founded in 1879, it’s the oldest restaurant in the city, and it’s particularly well-known for its turkey. And you’ll find turkey dotting the menu in several ways. 

You can get the house specialty, the Roast Young Tom Turkey, served with sage dressing, mashed potatoes, and cranberry sauce. But you can also get your turkey fill in other ways, like the Turkey Enchiladas and the Turkey Cream Cheese and Cranberry Sandwich.

Just got back from a food tour and can’t imagine taking another bite? You’re still going to want to check out Huber’s for drinks and dessert. From Baked Bread Custard Pudding to Housemade Pumpkin Pie, Huber’s really knows how to do the sweet stuff. 

But the main attraction here is the restaurant’s famous Spanish Coffee. Made with rum, Kahlua, triple sec, coffee, whipped cream, and nutmeg, you get drinks and a show with this specialty. Your bartender will flame the drink tableside. It’s a delightful treat and quite an attraction! 

Now that you’re all sugared up, let’s work off some energy at one of Portlanders’ favorite places to spend an evening, the Crystal Ballroom. This McMenamins venue is known for having one of the last remaining spring-loaded dance floors in the country, giving you a feeling of dancing on air. 

There’s music playing here every night, so you never know whose show you may end up catching. Finish the first day of your weekend in Portland by dancing the night away!

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Portland Weekend Itinerary – Day 2

You’re going to start the second day of your 3 days in Portland feeling like a local. Portland takes great pride in its food scene, with restaurants being filled with dishes made with locally-grown produce. If you’re a chef yourself or just appreciate some super fresh food, you’ll love exploring the Portland Farmers Market

Portland Farmers Market

Weekend in Portland 3 Days Itinerary: Portland Farmers Market

Taking place year-round on Saturdays on the Portland State University campus, this farmers market is a favorite tradition of the locals. This market has much more than delicious seasonal produce. Here you’ll find everything from Japanese-inspired French pastries to pierogies to tamales to plant-based cheeses. You could easily spend a whole morning tasting your way around the market, so that’s exactly what we recommend doing! 

Portland Saturday Market

Weekend in Portland: Portland Saturday Market

However, there’s another market on Saturdays that’s worth a visit. While the farmers market will give you a taste of Portland’s eclectic food scene, the Portland Saturday Market will remind you why they say to “keep Portland weird.” Running along the Willamette River, this market is the largest continually-operating arts and crafts market in the US.

Open from the beginning of March to the end of December, this market is filled with handcrafted goods made by local artisans. From items for your adventurous pup to goat milk bath products to “Star Wars” parody artwork, you never know what kind of hidden gem you’ll find here. 

Lechon

3 Days in Portland Itinerary: Lechon

When you’ve worked up an appetite, head over to Lechon, a South American restaurant serving up a killer tapas menu. This cozy restaurant is a great place to relax after walking around the markets all morning. 

It offers both traditional favorites, like Lomo Saltado, and more unique takes, like Vermicelli Dumplings. Order up a mix of whatever catches your eye to share with your whole party. You’re bound to leave here full and happy! 

Next up, catch a show at the Curious Comedy Theater. This comedy venue specializes in all things improv, so you’ll never see the same show twice. Check out the Curious Comedy Showdown, known as the “Hunger Games of Comedy,” where the best of the best of Portland’s comedy scene compete for the audience to vote to see who is left standing. 

Or give Love, Shakespeare a try, where comedians make their very own Elizabethan comedy each night. Or check out another unique show being offered the night you arrive. There are always shows running all weekend long.

Finish off the night with a drink and a bite to eat at the Keys Lounge, which is just a short stroll away. Housed in a locksmith building from the 1960s, this lounge specializes in comfort food and both classic and “remixed” cocktails. 

They also have a solid list of both low-proof and no-proof cocktails for those who can’t drink alcohol or who would prefer not to. Drink up alongside comfort food favorites, like fried chicken sandwiches and mac and cheese.

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Portland Weekend Itinerary – Day 3

Start the last day of your 3-day weekend in Portland over in Pioneer Courthouse Square to get one of the best breakfast sandwiches in Portland. Fried Egg I’m in Love’s food cart always has a long wait, but it’s also always worth it. 

They’re best known for their Yolko Ono sandwich, with fried egg, housemade pesto, and a sausage patty. But you can also find plenty more options, like the Egg Zeppelin, with two eggs, two sausage patties, two slices of cheddar, and housemade aioli.

Pioneer Courthouse Square

Portland 3 Day Itinerary Weekend Guide: Pioneer Courthouse Square

You may want to spend some time exploring around Pioneer Courthouse Square, as there’s plenty of shopping in this area. Oregon is one of only five states with no sales tax. So if you want to get some shopping done for less than you’d pay at home, you may want to consider filling up some bags in Portland!

Powell’s City of Books

3 Days in Portland Weekend Itinerary: Powell’s City of Books

But there’s one shop that’s only a short walk away that’s an absolute must-do: Powell’s City of Books. Stretched over a full city block and housing about one million books, Powell’s City of Books is the largest new and used bookstore in the world. 

Spend time getting lost in the shelves of this independent bookstore, finding new and old favorites alike to fall into. If you’re a book lover, it’s impossible to leave the store without a full bag of books to love.

Lan Su Chinese Gardens 

Next up, head over to the Lan Su Chinese Gardens for a peaceful afternoon. This beautiful garden is truly more than your typical botanical garden. It’s a celebration of Chinese culture that blends art, history, and nature. When you visit, you can also take part in daily events, like garden tours and demonstrations on everything from traditional Chinese exercises to art techniques. 

While you’re there, grab a seat at the teahouse. Take in the tranquil environment and breathtaking views as you enjoy a selection of teas and light bites, like dumplings and mooncakes. 

Ground Kontrol

3 Days in Portland Itinerary: Ground Kontrol

Your next stop is a unique arcade that’s a longtime favorite in Portland: Ground Kontrol. If you arrive earlier than 5 pm, feel free to bring little ones, but keep in mind that it’s only for 21 and older after 5 pm. 

This arcade specializes in all things retro. Battle it out on “Marvel vs. Capcom,” try to reach your high score on “Burger Time,” or play as your childhood heroes in “TMNT: Turtles in Time.” There are tons of games to choose from, and you can play while you sip on themed cocktails. 

Screen Door

Portland 3 Day Itinerary Weekend Guide: Screen Door

When all that gaming has worked up an appetite, you can grab some snacks and light bites here, or you can get a full dinner. Just a short walk away is Screen Door, which serves up classic Southern comfort food in a cozy setting. 

Absolutely start with the hushpuppies, which are served with a mouthwatering pepper jelly. Thankfully, this delightfully delicious restaurant serves their Chicken & Waffles during both brunch and dinner, so if you’re a breakfast-for-dinner person like us, you’ll want to order this beloved dish!

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More Places to Eat & Drink in Portland

Snap a photo at Voodoo Doughnuts:
We felt we couldn’t write a guide to Portland without mentioning this doughnut shop that arguably kicked off the doughnut craze. While we’re admittedly bigger fans of Blue Star Donuts, Voodoo has gone from its Portland roots to take off around the country, and it is pretty darn cool to see where it all started. Just be prepared for a long wait. You can’t go wrong with an Instagram-worthy Voodoo Doll doughnut, but if they have the Old Dirty Bastard, get that instead, especially if you believe the Peanut Butter Oreo is the superior Oreo.

Grab a drink at McMenamins Kennedy School:
Once an elementary school that opened in 1915, the Kennedy School is now a hotel, movie theater, restaurant, brewery, soaking pool, and several small bars. Defy your teachers by drinking in detention, see a movie, or spend a few hours in the pool, which is open to the public even if you’re not staying in the hotel. 

Get a cocktail at Teardrop Lounge:
This watering hole, known for its teardrop-shaped bar in the center, kicked off the cocktail craze in Portland. Each drink is made by a world-class mixologist, so you may have trouble choosing just one to order.

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Portland Timbers

3 Days in Portland Itinerary: Timbers

Catch a Timbers game. The Timbers are Portland’s Major League Soccer team, and the best way to party like a local is by cheering them on. If you’re visiting in the spring and summer, be sure to get a ticket to a game. If you want a truly local experience, arrive early to get a seat at the Timbers Army section.

First Thursday in the Pearl District

Portland 3 Day Itinerary Weekend Guide: Pearl District

Attend First Thursday. If you have a 4-day weekend in Portland and are coming in on the first Thursday of the month, head to the Pearl District. Here you’ll find talented artists selling their work, art galleries to peruse, live music, and food and wine samples throughout your stroll. It makes for a lovely night out, especially when the weather’s getting warmer.

International Rose Test Garden

3 Days in Portland Weekend Itinerary: International Rose Test Garden

See the flowers in bloom at the International Rose Test Garden. Located in Washington Park, this garden will make you understand why Portland is the City of Roses. If you visit between late May and October, you’re arriving right when more than 10,000 rose bushes are in bloom. It’s a stunning place to take a stroll, and it offers a great view of Mount Hood when the weather’s right.

F0rest Park and Pittock Mansion

Weekend in Portland 3 Days Itinerary: Forest Park

Hike through Forest Park. This park is one of the largest urban parks in the US and offers miles upon miles of well-maintained hiking trails. If you have time, be sure to visit the Pittock Mansion. This historic house has one of the best views of Mount Hood and Downtown Portland.

Oregon Zoo

Weekend in Portland: Oregon Zoo

See the animals at the Oregon Zoo. Located in Washington Park, this zoo is home to more than 2,000 animals and makes for a great way to spend a day in Portland, especially if you have little ones. If you’re visiting in the summer, be sure to check out if there are any summer concerts playing during your trip.


Getting Around Portland

Getting Around Portland, Oregon: Weekend Itinerary

To get to Portland, you’re most likely going to arrive at the Portland International Airport. It’s the largest airport in Oregon and the most convenient for starting your weekend in Portland.

From there, you have several options. You could rent a car, but it’s not entirely necessary. Portland has excellent public transportation, and you can even take the MAX Light Rail right from the airport. Taking the Red Line is one of the easiest ways to get to and from the airport. 

And the MAX Light Rail isn’t the only form of public transportation in Portland. You can also get around via the TriMet buses, the Portland Streetcar, and the Portland Aerial Tram. 

However, you may still want to consider renting a car if you plan on venturing outside of the city. If you want to go hiking around the Columbia River Gorge, see Mount Hood, or even take a day trip to Crater Lake National Park, the easiest way to get there would be by car. But you most likely would want to save the extra excursions for when you have more time to explore the area around Portland rather than trying to cram them in during your 3 days in Portland!

We hope you enjoy your weekend trip to Portland, Oregon! Should we add something else to our 3-day Portland itinerary? Let us know in the comments.


Planning a trip to Oregon? Check out our favorite travel guides and resources!


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About the Author:

  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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