3 Days in Portland: The 14 Best Things to Do on a Weekend Trip

When it comes to exploring the Pacific Northwest, there’s no base quite like Portland, Oregon. There’s plenty of urban culture and delicious food to fuel you up for adventures beyond the city limits too: browsing bookshelves, window shopping, chasing waterfalls, hiking volcanoes, or exploring the Pacific Coast. If it sounds like too much for a Portland weekend trip, you’ll be pleasantly surprised how much you can pack into 3 days in Portland!

I lived in Seattle for four years, and during that time I made many Portland weekend trips. I visited friends who lived there, met up with friends who were visiting, and had a few adventures on my own (or with Mr. V once we started dating!). While my heart will always be in Seattle (go Sounders!), I can see why so many people love visiting (and living in) Portland.

If you’re planning a trip to Portland and curious about what there is to see and do in the Rose City, read on. You’ll find a list of the best things to do in Portland – based on my trips – and an itinerary for 3 days in Portland which also includes an opportunity to adventure further in the Pacific Northwest.

In this post, I promote travel to a destination that is the traditional lands of the Stl’pulmsh (Cowlitz) and Clackamas peoples, the Confederated Tribes of Grand Ronde, and the Confederated Tribes of Siletz Indians. With respect, I make a formal land acknowledgment, extending my appreciation and respect to the past and present people of these lands. To learn more about the peoples who call these lands home, I invite you to explore Native Land.

This post was originally published in October 2014, and was updated most recently in August 2022.

Portland Travel Tips

Before launching into how to plan your Portland weekend trip, here are a few quick details on the logistics you need to know.

How to Travel to Portland

There are three ways to get to Portland: plane, train, and automobile!

• By plane: The Portland International Airport (PDX) is famous for its carpet; there are flights to/from Portland from around the country and world.
• By train: The Amtrak runs to Portland! There are three routes you can take to/from Portland: the Coast Starlight (which connects between California and Portland), the Cascades (which connects to Seattle and Vancouver), and the Empire Builder (which connects to Chicago).
• By car: Interstate 5 runs through Portland; I-84 does too. That means you can drive either of these main routes to reach Portland easily. If you’re planning a Pacific Coast Highway road trip and want to stop in Portland, it’s a short 90-minute detour inland from the PCH.

What to Pack for Portland

Uncertain what to pack, based on the weather and adventures you want to have? I’ve got a separate post all about what to pack for Portland. In short, be sure to pack good shoes, layers – including something to keep you dry – and sunglasses for those glorious days when the sun shines on the Pacific Northwest. Speaking of the weather…

When to Visit Portland

Portland has distinct seasons. Summers in the Pacific Northwest are dry, warm, and sunny, while the winter is grey and often rainy. In between, weather might change every few minutes!

If you love rain, you can visit any time and have a great trip to Portland; if you want to have the best chances for sunny, good weather, plan your trip to Portland in May through September.

The 14 Best Things to Do in Portland

Before suggesting an itinerary of how to spend 3 days in Portland, here are some of the best experiences you should try and have on your Portland weekend trip!

Browse the Shelves at Powell’s Books

Any city where one of the top sights is a bookshop is a great city in my opinion! That’s one of many reasons I like Portland – Powell’s Books is one of the world’s largest independent booksellers, and one of the city’s top attractions.

It’s easy to spend an hour or two exploring the shelves at Powell’s, which is close to downtown Portland. Don’t be surprised if you end up bringing a book or two home as your souvenir!

Eat All the Food!

If you do any research into visiting Portland for a weekend, you’ll see immediately that a weekend in Portland is not nearly enough time to eat all of the amazing food the city has to offer. Honestly – Portland completely lives up to its foodie reputation.

Here are some things to keep in mind as you plan your meals:

• Brunch is a competitive sport in Portland, so plan ahead and grab reservations if you can. Some of my favorite brunch spots in Portland include Tilt, Clyde Common, Tasty n Sons, and Olympic Provisions. Almost all require a reservation, or a willingness to wait for a table on the weekends.
• Portland’s food truck scene is top-notch. Most people don’t know that I started out my writing career reviewing food trucks – so when I started visiting Portland, I was all about the food trucks here. There are over 600 food trucks and carts to choose from; it’s impossible to try them all.
• There are plenty of amazing spots to choose from in every Portland neighborhood. If you’re planning a first trip to Portland, try to just explore one area and sample what that has to offer – whether that’s East Portland, Downtown, or the Pearl District.

Wander in Portland’s Neighborhoods

Speaking of neighborhoods, I highly recommend spending some time exploring 2-3 of the neighborhoods during your Portland weekend. Here are some of my favorite ones:

1. The Alphabet District – This primarily residential neighborhood is named for the streets, which go up in alphabetical order (Everett, Flanders, Glisan, etc.). It’s home to some amazing food and boutiques.
2. Goose Hollow – South across Burnside from the Alphabet District, there are a number of good restaurants, cool hotels, and Providence Park (where the Timbers play, boooo!) here.
3. The Pearl District – A great shopping area, the Pearl District is near Downtown Portland. You can find cute local boutiques and hip chain stores here, as well as some posh dining options.
4. Downtown Portland – Downtown Portland offers what most downtowns do: chain restaurants and stores, plus lots of businesses.
5. East Portland – There’s so much to explore east of the Willamette River that runs through the middle of Portland. If you choose to cross one of Portland’s 12 bridges to see what you’ll discover, I recommend the neighborhood of East Portland, which is full of great spots to eat and drink all day and all night.
6. Nob Hill – Located in Northwest Portland, this fashionable neighborhood is famous for its trendy boutiques and thriving gastromic scene. Every nook and crannie is replete with stores and restaurants from every corner of the world. Nob Hill is also home to 23rd Avenue, one of Portland’s prime shopping areas.

Learn City History at Pittock Mansion

I’ve been to Pittock Mansion several times; it’s a Portland landmark and has one of the best viewpoints in the city. (Two other great spots to see the Portland skyline: the Portland Aerial Tram (more below) and the Portland City Grill).

Pittock Mansion is a historic home with deep roots in the city’s history; publisher Henry Pittock and his wife, Georgiana Burton Pittock lived here during Portland’s gilded age. Mrs. Pittock was also responsible for planting roses on the grounds and helping establish the Portland Rose Society. (More on that below, too!).

Today you can take a guided tour of the home and learn about Portland history and the Pittock family.

Hike to Witch’s Castle

Nestled in Forest Park, Witch’s Castle is one of the latest Insta-famous locations in Portland. Despite its name, the structure has no connection to witchcraft. In fact, its formal name is Stone House, but students who hold parties there in the 80s dubbed it Witch’s Castle and the name eventually stuck.

The property has winessed its fair share of sinister events, though, with stories of doomed romances and bloody murders hidden in its past.

To tell this story we have to go back to the 1850s, when a man named Danford Balch bought a large portion of the land (today Forest Park) and hired Mortimer Stump to help him clear the area and build house. Little did he know that Mr. Stump and his daughter, Anna Balch, would end up falling in love. Balch never accepted the romance and refused to give Stump his blessing when he asked for Anna’s hand in marriage. The couple, determined to stay together against all odds, threatened to elope. This infuriated Balch who swore to kill Stump if they did. Ignoring the threats, the couple fled and got married in Vancouver. 

When Balch learned of the elopement, he became deeply depressed and spent his days drinking. But the worst was about to happen. One day, the couple returned to Portland to pick up his things. The moment Balch saw them, (true to his words), took out a double-barreled shotgun and shot Stump. After Balch’s arrest, conviction, and execution, the property was passed around through different hands throughout the next century, eventually bequeathed to the city of Portland. 

Now, the stone structure that we see today was built in 1930 and served as a park ranger station and restrooms for hikers until a storm heavy damaged it in 1962 and led to its abandonment. It was mostly forgotten until the 1980s, when local high school students found it was a fun place to hold parties. Today, nature has reclaimed the site, covering the structure with moss, vines, and weeds. 

Whether you call it Stone House or Witch’s Castle, this property has an unbeatable mysticism that you have to experience. 

Stop and Smell at the International Rose Test Garden

Not far from Pittock Mansion, you can learn why Portland continues to be called the Rose City. Down the hill in Washington Park, you can stroll among the rows and rows of rose bushes in the International Rose Test Garden. During the warm summer months, the rose bushes bloom in a variety of colors and smells – it’s a popular spot in Portland, but worth the crowds if you want to see the 10,000 bushes.

Get Zen at the Portland Japanese Garden

I’ve taken several trips to Portland, but I had never visited the Portland Japanese Garden until my most recent trip. It’s pretty easy to miss, actually – especially if you’re distracted by shops and dining spots in other parts of the city.

The Portland Japanese Garden is located in the Arlington Heights neighborhood (where we stayed in a fabulous! Airbnb; more on that below). It’s tucked away from prying eyes, but that helps cut down on the city noise and bustle to create a surprising oasis of calm.

Zen lawns, babbling fountains, and rock gardens make this space astonishingly peaceful and worlds away from hippie, hipster Portland. A few hours near the Koi pond left me far more restored and far less jet-lagged than a trip to Japan.

Stroll or Run in McCall Waterfront Park

On the west bank of the Willamette River, Governor Tom McCall Waterfront Park used to be somewhere you didn’t hang out a ton. The City has done a lot to improve the park and make it feel safe; it’s perfect for a walk, run, or bike ride on a nice Portland day.

McCall Waterfront Park runs from Steel Bridge in the north to Poet’s Beach in the south near the I-5 Bridge. In total, it runs 1.5 miles from end to end – a perfect length to stretch your legs!

Score Unique Goodies at Portland Saturday Market

Portland is such a diverse city. You see this, hear this, and smell this at the Portland Saturday Market. This outdoor arts and crafts market runs from March through December along Willamette River. The market has been operating since 1974, which has earned it the title of “the largest continuously operated outdoor market in the United States.”

With over 150 stalls, you can find stalls selling rocks, toys, clothing and hats, musical instruments, jewelry … you name it. Let me warn you in advance; it is impossible to go there and not spend money.

But what makes Portland Saturday Market truly special is the vibe. The mishmash of artisans, families, music performers, dogs, tourists, and food vendors creates a funky and convival atmosphere that’s palpable from the moment you set foot in it. Definitely a lovely opportunity to get a glimpse of Portlanders’ lives.

Smarten Up at OMSI

OMSI – which stands for the Oregon Museum of Science & Industry – is one of my favorite science museums. (And that says a lot because I love science museums!)

OMSI is located along the Willamette River on the east side and is a perfect activity for families or just adults like me who love to have their minds blown by the wonders of our planet and universe.

(When I was a kid, on my very first trip to Portland, I stayed overnight in the OMSI submarine on the river!)

Explore East Portland

While you’re over visiting OMSI, consider spending more time in East Portland. It’s long been the up-and-coming part of the city – though by now it’s well-established as a cool place to explore, dine, and drink. Some cool places in East Portland include:

• White Owl Social Club – A chill spot with burgers, beers, and – because it’s Portland – plenty of vegan options too.
• Cascade Brewing Barrel House – Famous for their barrel-aged sour beers and sandwiches.
• AFURI IZAKAYA – A fantastic Japanese restaurant with ramen and sushi in a reclaimed warehouse.
• Loyal Legion – A cozy dining spot with – I kid you not – sausages and global eats. Sounds like my kind of place!

Ride the Portland Aerial Tram

The Portland Aerial Tram is the only thing on my list that I haven’t actually done – but it’s so cool I had to include it! On the four-mile ride, you’ll get some incredible views of the city of Portland and, on a clear day, towering Mt. Hood and other Cascade mountains.

Find Your Favorite McMenamins

If you’ve browsed all the restaurants in Portland, you’ve undoubtedly seen the name McMenamins come up on the list a few times. This family-run business has a “chain” of pubs, breweries, restaurants, and dining experiences throughout the Portland area (and the whole Pacific Northwest) – but it’s not a normal restaurant chain, as each experience is totally different!

Here are some of the McMenamins to choose from:

• Blue Moon Tavern & Grill, in the Alphabet District
• Edgefield, on the way up the Columbia River Valley
• Barley Mill Pub, in East Portland

There are over 50 locations across the PNW though, so if you want to try and choose a few to try, check the whole list on their website.

Explore Beyond Portland on the Oregon Coast or Columbia River Valley

Technically this isn’t one of the best things to do in Portland, but if you’re visiting the Pacific Northwest – you have to explore! Portland is a great base for some adventures in Oregon and the rest of the Pacific Northwest. After all, Portland is only three hours from Seattle, and you know how much I’ve shared of adventures you can have from Seattle!

I have three favorite day trips from Portland to recommend if you’re visiting for a weekend:

1. The Oregon Coast – A short 90-minute drive takes you from Portland to the coastal town of Seaside. It’s a picturesque spot to admire the Pacific Coast in all its glory.
2. The Columbia River Valley – You can drive from Portland to Hood River in an hour along the Columbia River. Along the way, stop and admire the view from Vista House or stroll up to Multnomah Falls.
3. Mt. Hood – It’s a 90-minute drive from Portland to the Timberline Lodge on the slopes of volcanic Mt. Hood. Here you can hike and explore the mountain in any season (including on skis in the winter!).

If you have even more time, I put together a post on a number of great road trips from Portland you can plan with extra days.

3 Days in Portland: A Weekend Trip Itinerary

Now that you know the best things to do in Portland, it’s time to put it all together. If you only have a weekend in Portland, here’s how I’d pack in as many of these experiences as possible into 3 days in Portland!

Day 1: Arrive & Indulge

What you can do on your first of 3 days in Portland depends a lot on when you arrive. If you’re arriving by plane, you may have more of the day to explore and get oriented before seeking out dinner and drinks. If you’re driving to Portland, again your schedule may vary.

In any event, I recommend starting your Portland weekend trip with a delicious meal and drinks – the best Portland has to offer! If you’re uncertain where to start, check out my recommendations in East Portland – that’s the place to go.

Day 2: Explore Portland’s History & Neighborhoods

Rise and shine early for a full day exploring Portland. I recommend grabbing a coffee and pastry to hold you over until brunch, later in the morning.

Start the day by visiting Pittock Mansion, looking east across the city as it wakes up for the day. You can do a guided tour depending on the schedule that day, or stroll among the grounds to admire the view.

Next, stop by for a calming stroll through the Portland Japanese Gardens or Witch’s Castle. If you decide to visit the Gardens, it opens at 10 am each day unless you decide to become a member – then you can get in as early as 8 am!

After the Gardens, it’s time for brunch. Choose a brunch spot based on the neighborhoods you plan to explore, or consider heading to the Portland Farmer’s Market to browse the stalls and find a food vendor that looks delicious to you.

After lunch, strike out to explore Portland on foot. Be sure to swing by Powell’s Books at some point to stroll among the shelves. If you’re feeling hungry mid-afternoon, you should also plan to make it to Salt & Straw, Portland’s famous ice cream shop that has now spread all over the west coast!

For dinner, there are tons of choices. Whether you opt for a food truck (or three!) downtown, pop into a McMenamins like Blue Moon Tavern in the Alphabet District, or wait for a table with a view at Portland City Grill, you won’t be let down.

Day 3: Strike Out in the Pacific Northwest

On the final day of your 3 days in Portland weekend trip, you can stay in the city and visit some of the other places I recommended – or you can strike out on a day trip instead!

If you choose the day trip option, here are two ways to do it:

1. Drive east from Portland along the Columbia River. Stop for brunch at McMenamins Edgefield, and to enjoy the view from Vista House. Hike a bit at Multnomah Falls, before enjoying a mid-afternoon snack in Hood River. Head south and loop around Mt. Hood before stopping at Timberline Lodge for dinner.
2. Drive west from Portland to the Oregon Coast at Seaside. Stroll along the promenade and beach before enjoying a fresh seafood lunch, then turn your wheels south along the Pacific Coast. You can go all the way to Tillamook, where you can stop for a cheese-tasting snack. Head back to Portland for dinner.

Both of these are great options for a day trip from Portland, but there are others too! Love wine tasting? Research Willamette Valley wineries. Pop culture nerd? Look up Astoria, where The Goonies was filmed. There’s plenty more to explore…

Where to Stay in Portland

On my various trips to Portland, I’ve stayed every different way: with friends, in hotels, at vacation rentals. For your 3 days in Portland, here are my recommendations for the latter two options. (Sorry, my friend no longer lives in Portland so you can’t stay with her!)

Portland Hotel Recommendations

There are plenty of chain hotels in Portland, but here are a few hotels that I love:

• Hotel deLuxe – One of my first official partnerships with this blog was a stay at the Hotel deLuxe in Goose Hollow. This hotel is luxurious and cool in an old-school silver screen kind of way. From $116/night; book on Booking.com or Hotels.com
• Caravan: The Tiny House Hotel – If you’re up for an adventure, consider booking a tiny house! The Caravan Tiny House Hotel is near downtown Portland but has a fun PNW adventure vibe. From $145/night; book on Booking.com or directly

Portland Airbnb Vacation Rentals

• This loft is in the heart of the Pearl District (Portland’s main shopping area) from just $90/night
• This boutique apartment, which is next to my favorite neighborhood (the Alphabet District), from $85/night.
• On one trip, I stayed at Tom‘s place; it’s no longer listed though! (You can check his profile though to see if it’s relisted.) Two other options in the same area are this King’s Heights condo (from $114/night) or this Washington Park suite (from $87/night).

Do you have other questions about these things to do in Portland and how to plan your weekend visit? Let me know in the comments!

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