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The Ultimate 3 Days in Portland, Oregon Itinerary

The Ultimate 3 Days in Portland, Oregon Itinerary

Portland is a diverse and friendly city where being weird is cool, brunch is served every day, and an escape to nature is just minutes away. All you need is 3 days in Portland to understand why this city is one of the most unique destinations in the United States.

Donuts, craft beer, a peaceful Japanese and rose garden, a hike to the Witch’s Castle, and perusing the largest independent bookstore are just a few of the best things to enjoy in your Portland itinerary.

A weekend in Portland (2 days) is plenty of time to see the best sights. However, I recommend at least 3 days in Portland because it leaves room for an epic day trip. Portland is a great city to explore and the perfect hub for day trips to iconic destinations in Oregon, such as Mt. Hood, Cannon Beach, Willamette Valley, Multnomah Falls, and more.

As one of the best foodie cities in the country, experiencing the food scene is a huge part of a Portland itinerary. Food, coffee, and beer are more of a culture in this vibrant city. So the best thing to do with your 3 days in Portland is to eat and drink.

Therefore, this guide will include a large section dedicated to the best places to eat in Portland. It also includes the best time to visit, where to stay, how to get around, and the perfect 3 days in Portland itinerary.

Best Time to Visit Portland

Being in the heart of the Pacific Northwest, Portland has rainy months for most of the year. Thus, the best time to visit Portland is during its driest months, from June through September.

With that said, the summer months are the busiest time. So like any destination during high season, you can expect crowds at popular attractions, longer wait times at restaurants, and an increase in price for airfare and accommodations.

I recommend visiting Portland in June or September because it’s the beginning and end of high season. Another alternative is the springtime from April through May. The sun starts to shine more, and the city is graced with cherry blossoms and tulips.

Where to Stay 3 Days in Portland

Portland has four quadrants: NE, NW, SE, and SW. The city is easily divided by the Willamette River and Burnside Street. The Willamette River divides the east and west, whereas Burnside Street divides the north and south.

Most of the best things to do in Portland are on the west side of the river. Therefore, the Pearl District, Downtown Portland, and Northwest District are the best places to stay in Portland.

First-time visitors should stay in the Pearl District or Downtown Portland because they are the most convenient base for exploring the city. Both areas have hip boutique hotels that fit into the Portland culture. They also have accommodations for every budget, but the Pearl District is more on the up-scale side.

Getting Around Portland

As a family of five, we always prefer renting a car. It is the best way for us to travel, especially when we need three car seats. Therefore, I have yet to gain personal experience using Portland’s public transportation system, but it’s a fantastic way to get around the city.

I’ve created this Portland itinerary to make it easy and efficient to get around the city by public transportation, car, or foot. The 3 days in Portland itinerary is designed to explore specific areas in a day. Depending on where you stay, you may only need transportation for two days.

Portland has an easy and fantastic public transport system. The buses and MAX light rail system go to a majority of the popular attractions in the city. Everything is clean and efficient, and you can typically hop on a bus or train every 15 minutes.

Download the transit app, Hop Fastpass, on your phone for free. It’s a smart card for public transit fares that works on most transit modes. 

If you are staying in/near Pearl District, it’s a very walkable area where you may not need transportation for an entire day. The area is also bike-friendly. Therefore, some hotels will offer complimentary bikes to their guests.

If you rent a car, it will provide more freedom for day trips and flexibility.
Just keep in mind that parking in the city is difficult. The parking garages are insanely small, and a parking spot can be hard to find.

How to Spend 3 Days in Portland

The 3 days in Portland itinerary includes a day with nature, a day in the city, and a day for a quick trip. From hiking to a witch’s castle to smelling roses in the garden, shopping locally, getting lost in a bookstore, and more. The itinerary has ALL the best things to do in Portland, including where to eat.

Eating in Portland is a big part of enjoying the city and its culture. After all, Portland is one of the best foodie cities in the United States.

As foodies, we LOVED our dining experiences. Thus, my 3 days in Portland itinerary will include the best places to eat. For easy reading purposes, I will list where to eat each day and have a more in-depth, mouth-watering section at the end of the article.

Portland Itinerary Day 1: Forest Park and Washington Park

On the first day of your 3 days in Portland, start by exploring Portland’s urban Forest Park and Washington Park. These two beautiful parks have more than trees and trails to explore. There is a famous Japanese garden, an international rose test garden, a historic mansion, and a witch’s castle.

Find Tranquility at the Portland Japanese Garden

A flat garden inside the Portland Japanese Garden.

The Portland Japanese Garden is one of the most authentic Japanese gardens in the United States and best gardens in Portland. Walking through the garden, you will feel like you have made a quick trip to Japan.

Nestled in the hills of Washington Park, just outside the city, the proclaimed garden occupies 12 acres of tranquility. The Portland Japanese Garden features eight garden spaces showcasing different aspects of Japanese garden history and design.

Guests will find peace strolling through the different gardens, crossing a traditional Japanese garden bridge, and finding unparalleled views of Mt. Hood and the city. There is also an authentic tea house, koi pond, bonsai terrace, flat garden, cultural village, and more.

You can expect to spend two hours exploring the Portland Japanese Garden. And by the end of your visit, you will feel a sense of serenity and a connection to nature.

Stop and Smell the Roses at the International Rose Test Garden

Beautiful peach colored roses from the International Rose Test Garden in Portland, one of the best FREE things to include in a 3 day Portland itinerary.

The International Rose Test Garden is one of the best FREE things to do in Portland. It’s also across the street from the Portland Japanese Garden, making it the perfect second stop on your Portland Itinerary.

The International Rose Test Garden covers 4.5 acres and has over 10,000 individual rose bushes with over 600 rose varieties. It’s a gorgeous garden of vibrant colors filled with the prettiest and largest roses you will ever see.

Although the garden is beautiful year-round, the best time to visit the International Rose Test Garden is between May through October when the roses bloom.

Hike to Witch’s Castle

A boy walking up stairs at the Witch's Castle (stone house) in Forest Park, Portland.

If you are seeking a little adventure and local folklore, you must include a hike to the Witch’s Castle in your 3 days in Portland itinerary. It is one of the coolest things to do in Portland.

There are many tales, some more disturbing than others, of the Witch’s Castle (also called the Stone House), but one thing is sure – it is a sight to see.

You will not find any cauldrons brewing a concoction at Witch’s Castle, but you will find the “castle” covered in lush moss or graffiti art. Portland street art has lots of graffiti, so it makes sense that the castle maintains the “keep Portland weird” culture with graffiti on its ruins. It does look cool because the graffiti art colors pop in contrast to the lush forest.

The Witch’s Castle is located in Forest Park. You can access the 1-mile round trip trail from the Upper Macleay Parking Lot near the Portland Audubon Society. It is an easy 30-minute round-trip hike. Follow the “Stone House Trail” markers, and you will find the Witch’s Castle.

Explore the Grounds of Pittock Mansion

The outside of the historic Pittock Mansion - one of the best places to visit during your 3 days in Portland.

The Pittock Mansion is a French Renaissance-style historic house built in 1914 for one of Portland’s most influential families. Today, it is a museum for guests to learn about the transformation of Portland. From a pioneer town to a modern, industrialized city through the history and legacy of the Pittock family.

The 23-room Pittock Mansion connects visitors to early 20th-century life by showcasing a wide variety of period furnishings and personal artifacts from the Pittock family and other influential families of Portland.

Visitors can take a self-guided tour (or guided tour based on availability) of the exquisite mansion to see some furnished rooms such as the library, music room, Turkish smoking room, bedrooms, and more.

Although the inside of Pittock Mansion is a sight, many visitors skip a self-guided tour and enjoy the beautiful grounds for FREE. The Pittock Mansion sits on a steep hill that provides some of the city’s best views. On a clear day, you can see the five Cascade Mountains: Mount Hood, Mount St. Helens, Mount Adams, Mount Rainer, and Mount Jefferson.

Where to eat: Jam on Hawthorne, Blue Star Donuts, ¿Por Qué No? Taqueria, Cartopia (or any food cart pods)

Portland Itinerary Day 2: Downtown Portland (Pearl District)

On your second day of 3 days in Portland, it is time to explore downtown Portland and the well-known Pearl District. From a famous bookstore to the world’s smallest park, the largest continuously operated outdoor market, and craft breweries – you will experience the vibrancy of Portland.

Shop Locally at the Portland Saturday Market

If you are visiting Portland on a Saturday, I recommend spending your morning at the Portland Saturday Market. It is the country’s largest continuously operated outdoor arts and crafts market.

The outdoor market features over 250 artisans and local small businesses that create beautifully handmade arts, crafts, and foods from the Pacific Northwest region. From handmade soaps, jewelry, pottery, paintings, apparel, and more – it is the perfect place to find a souvenir from your 3 days in Portland.

The Portland Saturday Market is located in Portland’s historic Old Town at Waterfront Park and Ankeny Plaza. It operates from 10 am to 5 pm every Saturday, March through December 24th.

Read a Book at Powell’s City of Books

An aisle of books at the iconic Powell's City of Books - a visit to this independent books store is essential for any 3 days in Portland itinerary.

Whether you love to read books or not, a visit to Powell’s City of Books needs to be on your Portland itinerary. This enormous bookstore is one, if not THE, most iconic place in Portland.

Powell’s City of Books is the world’s largest independent bookstore that sells new and used books. There are over 3,500 sections spread throughout three floors and ten different rooms.

If you do not get lost in a book, you will get lost finding your way through the bookstore. Thankfully, staff members provide a map to help you navigate – seriously, you want to grab one.

Eat a Voodoo Doughnut!

The famous Voodoo doll donut in Portland, Oregon.

Some tourists and locals will say Voodoo Doughnuts is a tourist trap. It may be, but I think eating their doughnuts during your 3 days in Portland is worth it.

Voodoo Doughnuts offers more than 50 artisanal donuts but is most famous for the classic Voodoo Doll, Bacon Maple Bar, Memphis Mafia, and The Cannolo – you should order at least one of these donuts. They are also one of the best spots for vegan donuts in Portland, with over 25 vegan options.

You can see all the donuts rotating in a fun donut carousel. There are classic donuts and quirky flavor combinations too. The names of the donuts are also a part of the fun voodoo experience. Be warned; some names are not too kid-friendly.

The donuts are as delicious as they look – not overly sweet and very fluffy. They are also huge! Overall, I say Voodoo Doughnuts are worth the hype.

There are many locations in Portland, but the original site is just a few blocks from Powell’s City of Books. So you can expect to see the line wrapped around the block, which, luckily, moves at a reasonable pace.

“Play” at the Smallest Park in the World

Mill Ends Park is the world’s smallest park that consists of one tree on a two-foot wide plot and a colony of leprechauns. Yes, you read that right.

The origin story of Mill Ends Park began in 1946, when an imaginative Irish journalist, Dick Fagan, planted flowers into this small hole. In Fagan’s column “Mill Ends,” he published fantastical stories of a colony of leprechauns that resided in his little park. He claimed that a leprechaun granted him one wish, a park of his own. However, Fagan didn’t specify the size, so the leprechauns gave him a tiny hole for his park.

Honestly, I love this park and its story. It is quirky and fun, which plays into the “keep Portland weird” culture. And yes, Mill Ends Park is the world’s smallest park, per the Guinness World Record.
The tiny urban park is located in downtown Portland on the median strip of Naito Parkway and Southwest Taylor Street.

Enjoy Local Craft Beer

Two glasses and one can of beer from Breakside Brewery - one of the best breweries in Portland.

With more than 70 breweries in town, Portland sells more craft beer than anywhere in the country. The city has been dubbed the beer capital of the United States. Moreover, the Pearl District is home to the historic Brewery Blocks, where the legacy of Portland’s craft beer began.

Thus, one of the best things to do in Pearl District and Downtown Portland is to drink local craft beer. Whether you go on a brewery tour, brewery hop on your own, or kick back at one brewery – you should enjoy a pint of craft beer during your 3 days in Portland.

The Pearl District and NW Portland has some of the best and most award-winning craft breweries in Portland. A few favorites include Breakside Brewery, 10 Barrel Brewery, Von Ebert Brewery, Backwoods Brewery, and Deschutes Brewery.

Where to eat: Pine Star Biscuits, Screen Door, Salt & Straw

Portland Itinerary Day 3: Pick a Day Trip

On your last day, I recommend a taking a scenic drive from Portland and enjoy a day trip. Portland is a great city to explore, but it’s also a great hub city for day trips.

There are so many fantastic day trips from Portland. The hardest part is choosing which one. You can play in the sand at Cannon Beach, chase the best waterfalls in Columbia River Gorge, explore Mt. Hood and the Hood River Fruit Loop, or wine hop in the beautiful Willamette Valley.

Depending on when you return to the city, you can finish your 3 days in Portland at the Kennedy School – one of the most unique places in Portland. You can grab a drink at detention, soak in thermal waters, and watch a movie.

No rental car? No Problem! Since day trips from Portland are popular, you can easily find group tours to these destinations.

Play in the Sand at Cannon Beach

The iconic Haystack Rock at Cannon Beach.

One of the best day trips from Portland is Cannon Beach. Cannon Beach is one of the most famous beaches in the world, and rightfully so. Rain or shine, this beach is magical.

Take a stroll along the beach, fly a kite, explore tidepools, enjoy delicious food and craft beer at Pelican Brewery, and of course, soak in the beauty of Haystack Rock. Cannon Beach is one of the best stops on the Oregon Coast.


Chase Waterfalls at Columbia River Gorge

Multnomah Falls, the iconic waterfall in Columbia River Gorge

Columbia River Gorge is one of the most popular and accessible day trips from Portland. Moreover, people mostly take the opportunity to see the majestic Multnomah Falls.

There are over 238 waterfalls in Oregon, but none are as iconic as Multnomah Falls. The 620 ft. two-tiered waterfall is one of the country’s most recognizable and famous waterfalls.

It is undoubtedly the most famous waterfall in Oregon because of its magnitude, but more importantly, it is easily accessible to visitors. Multnomah Falls is only a 30-minute drive from Portland and a short distance from the Historic Columbia River Highway. It is essentially a roadside attraction.

Again, there are over 238 waterfalls in Oregon, and at least 90 of them are in Columbia River Gorge. In addition to Multnomah Falls, you can also visit and hike to seven more beautiful waterfalls in the Columbia River Gorge – all in one epic day.


Explore Mt. Hood and Hood River

A pristine view of Trillium Lake and Mt. Hood

During your 3 days in Portland, you will probably see the magnificent Mt. Hood in the distance. It is a sight to see from afar, but it’s absolutely breathtaking up close. 

In Mt. Hood, you can drive to the top and explore the historic Timberline Lodge, where scenes of The Shining were filmed. You can also hike a part of the Pacific Crest Trail and hit the slopes. In fact, Mt. Hood is the only place in the country where you can ski/snowboard year-round! 

After you explore Mt. Hood, descend the mountain and enjoy time at Trillium Lake and the Hood River Fruit Loop.

Hood River is known for its Fruit Loop – a trail of 28 orchards, fruit stands, wineries, breweries, cideries, and lavender fields. Frolic in lavender fields, pick fruit, grab a freshly baked fruit pie, and drink delicious cider, beer, and wine from the fruits of the local orchards. 

Read next: Best Stops on the Hood River Fruit Loop

For a truly epic day trip, you can easily see Multnomah Falls on your way to Hood River and Mt. Hood. 


Enjoy Wine Tastings in Willamette Valley

A view of vineyards in the Willamette Valley at Stoller Estate.

The Willamette Valley is home to over 700 wineries in a 150-mile-long valley in Oregon. It is recognized as one of the best wine regions in the country and one of the best-producing Pinot noir regions in the world.

In addition to drinking world-class wine, you will also drink in gorgeous views of Willamette Valley. Several wineries sit atop a hill to provide guests with stunning views of the estate’s vineyard, rolling hillsides, and deep valleys. And on a clear day, you might see Mount Hood and Mount St. Helens.

Read next: Best Wineries in Fredericksburg, Texas

Most wineries in the Willamette Valley require reservations. So I recommend booking reservations at two to three wineries. Our two favorite wineries are Willamette Valley Vineyards and Stoller Family Estate.


Go to Detention at the Kennedy School

Who is ready to serve detention at the Kennedy School? The Kennedy School is an old elementary school from 1915 that has become a boutique hotel and brewery. It is a unique place and a fun way to end your 3 days in Portland.

The Kennedy School has 57 guest rooms, a restaurant, multiple bars (including a detention and honors room bar), a movie theater, a soaking pool, a gift shop, and a brewery. There is so much to enjoy at “school”; you will want to spend your entire day here – probably something you never thought you wanted.

Where to eat: Pip’s Doughnuts and/or Proud Mary Coffee Cafe, Kennedy School

Where to Eat for 3 Days in Portland

Did you know that brunch is HUGE in Portland? You do not have to wait till Sunday morning to enjoy brunch. Brunch is served every day in Portland.

To ensure we enjoyed all the best restaurants in Portland, we ate brunch twice a day – and we have no regrets. Ideally, you want four mornings in Portland to squeeze in one more brunch before a flight or drive home.

Moreover, this mini food guide of Portland includes all the best things to enjoy in the city – coffee, donuts, brunch, food carts, and Salt & Straw ice cream.

Stumptown Coffee Roasters

Being in the PNW, Portland is known for its coffee culture, with local, independent coffee shops on almost every block. Stumptown Coffee Roasters is one of Portland’s best and most beloved coffee shops.

Stumptown Coffee Roasters sources its coffee beans with direct trade from farmers worldwide. Then they roast the coffee beans in-house to brew the perfect cup of joe.

All the coffee options are spectacular, but Stumptown Coffee Roasters is famous for its cold brew. They even sell cold brew in cans! So grab a cup or a can of Stumptown’s cold brew, and enjoy it while exploring the city.

Must order: Cold Brew or Nitrogen Cold Brew.

Proud Mary Coffee Cafe

Birdseye view of a latte and hotcakes from Proud Mary Coffee in Portland.

Portland is one of the first outposts from the widely popular Australian coffee chain, Proud Mary Coffee. This Aussie-inspired coffee shop focuses on high-quality coffee and food – a combination they believe should go hand in hand.

Thus, Proud Mary Coffee Cafe is a table service cafe that serves all-day brunch, high-end tea, fresh juice, smoothies, freshly baked pastries, and the finest coffee. The food is so delicious and exquisitely presented; you will think you are at a fine-dining restaurant. At the same time, the staff is friendly, and the atmosphere is cozy; you will feel at home.

In addition to the food, one of the best things to enjoy is the coffee pour-over flight. The experience is like drinking wine; you can taste every note in the coffee bean.

Must order: Ricotta Hotcakes and a coffee pour-over flight.

Blue Star Donuts

A box of four gourmet donuts from Blue Star Donuts in Portland. Some of the best gourmet donuts ever!

Hands down, Blue Star Donuts are some of the BEST gourmet donuts in the country! Moreover, these are donuts for grown-ups – ooo that rhymes (but there are a few options for kids too).

Blue Star Donuts create gourmet donuts with unique flavor combinations using the freshest ingredients of herbs, spices, and fruits that are typically combined with liquor. Hence, donuts for grown-ups.

The menu includes delicious old-fashioned and vegan cake donuts, but the signature 18-hour brioche dough donuts are beyond amazing! The brioche donuts are some of the lightest and fluffiest donuts imaginable.

Must order: Blueberry Bourbon Basil, Lemon Poppy Old-Fashioned, Lemon and Lime Curd, and The O.G. (Orxata Glaze).

Pip’s Original Doughnuts & Chai

A plate of 8 mini donuts from Pip's Original Doughnuts and Chai Shop - one of the best places to eat in Portland.

Another fantastic donut shop in Portland is Pip’s Original Doughnuts & Chai – the world’s first doughnut and chai shop. Pip’s Original Doughnuts & Chai shop specializes in fried-to-order mini donuts and house-made chai from secret family recipes.

The mini donuts are two perfect bites of a crisp, golden brown exterior with a soft cake-like interior. There are five classic flavors and one rotating seasonal flavor. The classic flavors include cinnamon sugar, raw honey with sea salt, Nutella with sea salt, candied bacon maple, and cinnamon sugar with Nutella and honey.

Must order: Honestly, order at least two of each flavor, but The Reggie Lee (cinnamon sugar with Nutella and honey) is my favorite.

Jam on Hawthorne

A foodie Portland itinerary should always include Jam on Hawthorne. Since 2018, it has been voted Portland’s Best Brunch every year.

Jam on Hawthorne is a neighborhood breakfast cafe known for delicious breakfast served in huge portions. From a wide variety of mimosa flavors and Bloody Marys to vegan, vegetarian, gluten-free, and meat options – there’s something for everyone. No wonder why Jam on Hawthorne is a crowd favorite.

Must order: Bennie Hashbrowns, Grand Marnier French Toast, and your choice of a mimosa or Bloody Mary.

Pine State Biscuits

The owners of Pine State Biscuits grew up in North Carolina and brought a bite of the Southeast to the Northwest. Pine State Biscuits has the best buttery, flaky, homemade biscuits in the Pacific Northwest Region.

You can order a signature biscuit sandwich or biscuits smothered in gravy. You cannot go wrong because even the gravy is delicious, but the biscuit sandwiches are the real deal.

Although the homemade biscuits are the star of the show, Pine State Biscuits also offers other southern classics such as chicken pot pie and shrimp-n-grits. And save room for their homemade pop tarts and biscuit beignets.

Must order: The Reggie Deluxe – fried chicken, egg over easy, bacon and cheese topped with your choice of gravy. End on a sweet note with the Pop Tart of the month and Biscuit Beignets.

Screen Door

A plate of Screen Door's famous chicken and waffles.

The Screen Door is another southern staple in Portland that serves Louisiana-inspired southern cuisine for brunch and dinner. You can find true soul food that will knock your socks off, such as the famous chicken & waffles and praline bacon.

Trust me. This isn’t just any chicken and waffles. It is crispy buttermilk chicken with sweet potato waffles. Both are delicious, but the chicken is outstanding – and you can order one, two, or three pieces with your waffles.

The Screen Door is one of the most popular restaurants for brunch and dinner, so it is highly recommended to book reservations.

Must order: Chicken & Waffles, Bananas Foster French Toast, and Praline Bacon.

¿Por Qué No? Taqueria

Tacos from Por Que No Taqueria in Portland, Oregon.

¿Por Qué No? Taqueria is a popular Mexican restaurant serving the best authentic tacos in the city. The menu offers twelve different tacos, including carnitas, carna asada, chorizo, fish, and more.

The taqueria uses natural ingredients, sustainable seafood, and hormone, antibiotic-free meats. And organic corn tortillas are handmade every day.

The quality of care and passion to bring the best ingredients into a taco is evident. After one bite, you will see that the tacos at ¿Por Qué No? are as fresh and delicious as any in Mexico.

Must order: Carna Asada, Pescado, Carnitas, and Barbacoa.

Food Cart Pods – Cartopia

Thanks to its legendary food cart scene, Portland is home to some of the world’s best street food. Instead of having food carts parked and scattered around the city, Portland has created food cart “pods”.

A pod is where several food carts will stay in a single location. Each pod location also has its own unique name too. It makes for a fun foodie experience because guests can explore different food carts in one sitting.

There are over 500 food carts and over 25 pods in Portland. A few popular pods in Portland include Cartopia, Cartlandia, Hawthorne Asylum, Prost Marketplace, and St. Johns Food & Beers Porch.

During our 3 days in Portland, we ate at Cartopia, which ended up being one of our favorite dining experiences on the trip. Cartopia offers Latin-inspired chicken, healthy and fresh Thai food, twice-fried Belgian-style fries, juicy burgers, wood-fired pizza, and more.

Salt & Straw

A ice cream flight of four flavors with homemade waffle chips from Salt & Straw in Portland, Oregon.

Who is ready to scream for some ice cream? If you have a sweet tooth for ice cream, a trip to Salt & Straw is a must for your Portland itinerary.

Based in Portland, Salt & Straw is one of the best ice creameries in the country that has grown exponentially across several states. All thanks to its devoted community, passion for its craft, and devotion to using the best ingredients from local farmers.

Salt & Straw does not stray away from unique flavor combinations; they embrace it! In addition to classic flavors, you will find flavors such as Pear & Blue Cheese, Arbequina Extra-Virgin Olive Oil, and Strawberry Honey Balsamic with Black Pepper. And guess what? These flavors are delicious!

Must order: Sea Salt w/ Caramel Ribbons, Chocolate Gooey Brownie, Arbequina Extra-Virgin Olive Oil, Cold Brew Coffee Cashew Praline, and Strawberry Honey Balsamic with Black Pepper.

We fell in love with the city’s food, people, and vibrancy. We embraced the “weird” culture and hope you will too.