A weekend in Portland Oregon

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A Weekend In Portland (19+ Best Things To Do During Your Trip To Portland)

Best Things to Do For a Weekend in Portland Oregon

Located 60 miles to the east of the Pacific Ocean, right on the Columbia and Willamette rivers, you will find Oregon’s most populated city, Portland. As you set foot in the city, the first thing to grab your attention is the magnificent view of the snow-capped Mount Hood.

But, apart from that, you will also find several parks, bridges, bicycle trails, breweries, and coffeehouses in Portland that are enough for you to spend a memorable weekend. 

I lived in Seattle for six years and frequently took weekend trips to Portland. Although Seattle remains dear to me—it’s where August and I first crossed paths—I get why Portland is appealing both as a place to visit and as a launching point for exploring unique nearby attractions or taking scenic drives from Portland.

So, if you’re planning a getaway to Oregon’s largest city, here are the best things to do for a weekend in Portland to make your visit memorable and worthwhile!

Who This Portland Weekend Itinerary Is For?

We designed this Portland weekend itinerary for visitors who want to pack in as many fun and memorable experiences as possible in a short amount of time.

Regardless of your travel companions, this itinerary is designed to give you a taste of what Portland has to offer and leave you wanting to come back for more.

How Far Is Portland Oregon From?

  • Seattle: 2 hrs 45 min
  • Cannon Beach: 90 Minutes
  • Hood River: 1 Hour
  • Eugene: 1 Hour 40 minutes

What Is The Weather and Temperatures Like in Portland?


Things To Do To Create The Best Portland Oregon Itinerary

Regardless of whether you’re a local looking to get out and enjoy the city or a tourist trying to plan a Portland, Oregon Vacation, these ideas for things to do on your Portland trip are sure to keep you busy all weekend long.

Day 1 Of Your Portland Weekend

Day 1 of your Portland weekend kicks off with bustling downtown explorations, flavorful food truck bites, the farmers market, and the various Portland districts.

Dive into Portland’s vibrant culture this weekend with a curated list of must-visit spots and activities. From its bustling food markets to its eclectic art scenes, the city promises an unforgettable experience for every traveler.

1. ☕️ Stumptown Coffee

I can’t think of a better way to immerse yourself in Portland’s famed coffee culture than with a visit to Stumptown Coffee Roasters.

This place is more than a coffee shop; it’s a coffee experience. The vibe is artsy, laid-back, and absolutely Portland. Whether you opt for their Nitro Cold Brew or a comforting cappuccino, your day is off to a great start.

Stumptown Coffee has a couple of different locations throughout Portland but our favorite spot is the one located on 3rd Ave.

2. 🍩 Stop.. It’s Donut Time

Portland’s more than just its famous bridges and dynamic arts community—it’s also a paradise for fans of donuts! Explore an array of innovative flavors and artful designs all around the city. Whether you’re into timeless sugar-coated classics or adventurous new twists, there’s something for everyone.

Option A: Quirky Donuts At Voodoo Donuts (1 Min. Walk from Stumptown Coffee)

Alright, donut aficionados, ever been to Voodoo Donuts? If not, oh boy, are you in for a surprise. It’s more than just a donut shop; it’s a Portland legend.

From their iconic pink boxes to the eccentric and oh-so-tasty varieties (think bacon-topped or cereal-sprinkled delights), every bite screams ‘Portland Original’.

Option B: Adult Donuts at Blue Star

Unlike any donut shop, Blue Star offers gourmet donuts, such as the “Blueberry Bourbon Basil” or “Passionfruit Cocoa Nib.” Made from a classic brioche recipe, every bite is a mix of sophistication and nostalgia.

If you’re like me and can’t resist a great donut, kickstart your morning at Blue Star Donuts, the go-to spot for “Donuts for Grownups.”

3. Stroll Around Pioneer Courthouse Square

After you’re fueled up for your day with some coffee and donuts head over to Pioneer Courthouse Square. This is not just any city square, but a bustling urban plaza often filled with events, art installations, or just locals enjoying their day. The Square is known as the “people’s park” and is a great place to go to people watch, or just to relax.

The Square is also surrounded by some of the best restaurants and food trucks in Portland, so if you find yourself hungry, there are plenty of options.

4. Walk Or Jog Along The Tom McCall Waterfront Park

Want to have a full view of Portland? Visit the Tom McCall Waterfront Park! 

It is located right at the riverfront and is an excellent place for a small picnic or walk. And, if you’re in for some color, head over to the North end of the park to have a look at the Cherry Blossom trees

Also, if you stroll towards the South end of the park, you’ll find Salmon Street Springs, an outdoor water fountain.

🙋‍♀️Did you Know? A computer operates this water display, cycling up to 4,924 gallons per minute across 137 of its 185 jets. The three display modes it cycles through include misters, bollards, and even a wedding cake.

5. See Or Walk Across The Broadway Bridge

Broadway Bridge is, without a doubt, one of the most iconic landmarks in Portland. The bridge’s industrial-steel architecture perfectly embodies Portland’s rustic, industrial roots.

It offers a great view of the downtown Pearl District and the rest of Portland’s waterfront to the north and south. On a clear day, you can see Mount Hood in the distance.

The Broadway Bridge spans the Willamette River. It is accessed from the Pearl District near Union Station and connects to the Lloyd District. The bridge has two decks for vehicular traffic and sidewalks on both sides.

6. Shop At The Portland Saturday Market

The Portland Saturday Market is a weekly market located in downtown Portland that takes place at Tom McCall Waterfront Park. It features hundreds of vendors selling everything from handmade jewelry to fresh produce.

However, it isn’t just any ole market; it’s a vibrant celebration of creativity, crafts, and culture.

7. Lunch At Portland Food Trucks

if you haven’t dined at Portland’s iconic food carts, you’re truly missing out! The food trucks are a huge part of the local culture in Portland. There are over 500 food trucks in the city, and you can find pretty much every cuisine and price point too.

Nestled in various “pods” across the city, these carts serve up global flavors, from spicy Thai delicacies to rich, savory Mediterranean wraps.

Dive into the bustling hub at Alder Street Food Cart Pod, a smorgasbord of culinary delights right in the heart of downtown.

☞Insider Tip: The best way to find out what food trucks are where is to use the PDX Food Trucks app.

8. Navigate Portland’s Neighborhoods And Districts

One of the true joys of Portland? It’s a city of neighborhoods, each with its own distinct flavor, culture, and charm.

  1. Downtown Portland: Oh, the heart and soul of city! From the food carts that’ll have you drooling to the parks perfect for a little break, it’s the city’s buzzing epicenter.
  2. Pearl District: Once old warehouses, now it’s all about those chic vibes. Art lovers, this one’s for you. With galleries galore and cafes that are vibey.
  3. Alphabet District (Sometimes referred to as Northwest or Nob Hill): Charming streets lined with boutiques where you might just find your next favorite thing. Grab a coffee, sit back, and just take in that quaint urban charm. Ever wondered about its unique name? The east-west streets here follow an alphabetical order, making it both fun and easy to navigate!
  4. Hawthorne District: Bohemian vibes are alive and well in Hawthorne. From the iconic Bagdad Theater showcasing indie films to thrift stores where you can find the quirkiest treasures, it’s a nostalgic ride with a contemporary twist.
  5. Alberta Arts District: If there’s a heartbeat to Portland’s art scene, Alberta is it. Streets here burst with murals, quirky cafes, and monthly art walks. Each shop and gallery has a tale.
  6. Mississippi Avenue: Retro meets modern in this eclectic stretch. Independent boutiques, live music spots, and an array of food trucks make it a hive of activity. Meander the ave, and discover a hidden jazz bar.

9. Learn About The Pittock Mansion

The Pittock Mansion is one of Portland’s must-see attractions. The mansion was built for Henry Pittock, a prominent Oregonian publisher, and his wife, Georgiana.

The Pittocks were avid collectors of art and furniture, which is displayed throughout the mansion. The mansion is a French Renaissance-style château perched high in the West Hills with views of downtown Portland and Mount Hood.

Visitors can take a tour of the home or just explore its West Hills location for natural beauty and panoramic city views.

 10. Visit The Pearl District

The Pearl District is a neighborhood in northwest Portland that is known for its art galleries, upscale restaurants, boutiques, and lively nightlife.

There are plenty of things to do in the Pearl District, but some of our favorites include visiting the nearby Powell’s City of Books, checking out the exhibits at the Portland Art Museum, and grabbing a drink at one of the many trendy bars and breweries.

Pearl District has become a popular destination for beer lovers in recent years, with several microbreweries opening up shop in the area, so if you’re a fan of beer, this is a great place to be.

A. Powell’s Books In The Heart of Pearl District

Photo From Travel Portland

What’s so special about a book store, you ask? It’s the largest independent book store in the world!

This book store has nine color-coded rooms, 3500 different sections, and has approximately 1 million books for every genre! You can even find some books that are known to be long-lost in Powell’s!

So, if there’s a book that you have been looking for and cannot find anywhere, check out Powell’s City of Books. I’m sure you’ll find it among the impressive collection!

12. Dinner Time At Afuri Ramen + Dumpling

As evening falls in Portland, it’s time to spice things up with some Japanese flair! Dive into, Located in the heart of the city. From their yuzu shio ramen, which is a citrus-infused delight, to the steamed gyoza, each bite promises a taste journey.

The ambiance? A sleek, contemporary space that radiates Portland’s cool vibes. A heads-up: the place can get busy, especially during dinner hours, so perhaps aim for an early meal or have some patience in tow. Kampai to a delectable evening!

Day 2 Of Your Weekend In Portland

If you managed to get a good night’s sleep, well done! If not, don’t worry, there’s plenty to keep you energized and active today. Remember at the start of this itinerary I did say we’d be cramming in as much as possible.

Day 2 of your Portland weekend promises a blend of urban exploration and nature, ensuring every moment is packed with fun.

1. Enjoy Sunrise Along The Columbia River Valley And Multnomah Falls

multonomah falls

Before the city wakes and the crowds form, we’re heading out. Just 25 miles east of Portland lies the Columbia River Gorge.

It’s a nature enthusiast’s dream with dense forests, well-marked hiking trails, and impressive waterfalls to explore.

Some of our favorite waterfalls along the Colombia River Gorge are:

  • Multnomah Falls
  • Horsetail Falls and Ponytail Falls
  • Oneonta Gorge
  • Latourell Falls.

Pro-Tip: This area gets REALLY busy in the summer so it’s best to arrive early so you can find a place to park

2. Breakfast Time At Screen Door (East Side)

After an early morning of the Colombia River Gorge and a hike or two its time for a hearty breakfast. Situated in the East Burnside neighborhood, Screen Door is a must-visit for breakfast. Southern cooking meets the Pacific Northwest here.

Imagine crispy buttermilk fried chicken stacked on a fluffy waffle. Yes, it’s as good as it sounds!

Their praline bacon is another great choice that’ll have your mouth watering. With its vibrant atmosphere and generous portions, it’s a Portland staple for a reason.

3. Choose Your Afternoon Adventure In Portland

I’s time to pick your adventure. Don’t fret; you don’t have to do it all (unless you’re that ambitious, and kudos if you are!).

I’m including three options for you to choose from all three options are in the same area so take your pick of what you’re feeling up for

Option A: Hike To The Witch’s Castle

Witch’s Castle, formerly known as the Stone House in Forest Park, is an old roofless stone structure. Originally a ranger station, it was damaged in the 1960s and now sports graffiti.

Its spooky reputation and Instagram allure make it popular, so expect crowds unless you visit early. Though dubbed “Witch’s Castle” during the 80s party scene, it has no ties to witchcraft.

  • Learn more about the history of the Witches Castle here.
  • Learn about the 1 mile hike and how to access the trailhead here.

Option B: International Rose Test Garden (Across From The Portland Japanese Garden)

If you’re a fan of fresh blooming flowers, then the International Rose Test Garden is your place! 

Nestled in the city’s West Hills, this blooming haven boasts over 10,000 rose bushes of 650 varieties. Not only is it a sensory delight, but it’s also a working test garden where new rose varieties are evaluated.

Best time to go? Late spring to early summer when the blooms are in full spectacle.

Option C: Portland Japanese Garden (Across From The International Rose Test Garden)

Heading to the Portland Japanese Garden is a must when you’re in town. Located in the West Hills, this garden showcases authentic Japanese landscaping right in Portland.

With koi-filled ponds, traditional structures, and eight distinct garden sections, it’s a perfect blend of Japan’s design principles and Oregon’s natural beauty.

A great spot for a walk or some photos, it’s a refreshing change from the city’s hustle

4. Take A Ride On The Portland Aerial Tram

Hop on the Portland Aerial Tram for a unique view of the city. Starting in the South Waterfront, this short $8 round trip ride gives you a bird’s-eye view of Portland’s skyline and the Willamette River.

A must-do, especially if you appreciate scenic city views.

Pro Tip: Consider timing it around sunset for a special treat.

5. Take A Bike Tour Of Portland

Two wheels and an appetite for discovery? Perfect! Dive deep into Portland’s unique vibes on a bike. This city is seriously bike-friendly and full of charming neighborhoods, historic sites, and restaurants best experienced pedal-powered.

6. Brewery Time In Portland

If you’re a fan of craft beer, Portland is your playground. The city is teeming with breweries, each offering their own unique take on hops and brews.

Deschutes Brewery is a local favorite for their diverse lineup, while Cascade Brewing specializes in sour beers.

For something truly unique, head to Hair of the Dog, where each beer is a one-of-a-kind creation.

Whether you’re a casual sipper or a beer aficionado, there’s something here for every palate.

Our Favorite Portland Breweries:

  1. Deschutes Brewery: Originally from Bend, Oregon, Deschutes has a fantastic brewpub in Portland’s Pearl District. They’re known for classics like the Black Butte Porter and Fresh Squeezed IPA.
  2. Breakside Brewery: Located in the Woodlawn neighborhood, Breakside has gained acclaim for its vast variety of beers, from IPAs to unique experimental brews.
  3. Hair of the Dog Brewing Company: This brewery is well-respected for its age-worthy beers and strong ales. If you appreciate beers with depth and complexity, this spot is a must-visit.
  4. Cascade Brewing Barrel House: For fans of sour beers, Cascade is a paradise. This brewery has been a pioneer in the American sour beer movement, with a tap list that offers a rainbow of tart and fruity options.

🍺 If you’re looking for someone to take the guesswork out of your brew hopping experience; join a brewery hopping tour here.

7. Take a Food Tour 

When in Portland, taking a food tour is a must-do. This city isn’t just known for its stunning landscapes; it’s a culinary powerhouse!

Take a walking tour through Portland’s buzzing streets and hidden alleyways to uncover local foodie secrets.

From gourmet doughnuts to artisanal cheeses, and the freshest farm-to-table delights, every stop is a delightful surprise. And don’t even get me started on the food trucks!

8. The Entertainment Center and Soaking Pool at Kennedy School (McMenamins)

The McMenamin’s Kennedy School was once an elementary school but has been turned into a full-fledged entertainment center with a hotel, several restaurants, bars, a movie theatre, and the renowned soaking pool!

However, the soaking pool is the highlight of the place. If you visit Portland in the winter, you will definitely enjoy basking in the steamy outdoor pool.

Away from the hustle and bustle of the city, the McMenamin’s Kennedy School Soaking Pool is surrounded by serene gardens and a tranquil environment.

9. Ice Cream At Salt And Straw

Just like Voodoo Doughnuts has unique toppings, you’ll find unique ice cream flavors at Salt & Straw as well.

Salt & Straw is an ice cream shop with delicious handmade ice cream. What sets it apart is the out-worldly yet highly demanded ice cream flavors, including pear and blue cheese, Arbequina olive oil, and strawberry honey balsamic with black pepper. Yes, these are ice cream flavors, if you’re wondering! 

A Long Weekend In This Pacific Northwest City ( 3 Days in Portland )

If you have three days in Portland, here are a couple of extra things to add to your itinerary

10. Hike Or Walk Around Mount Tabor Park

There are almost 200 parks in Portland, but what’s so special about Mount Tabor Park? It’s built on top of a volcano! Not near, not around, but it sits right on top of the extinct Mount Tabor volcano!

What’s more interesting is that the walkways and trails of the park are paved using cinders from the ancient lava of the volcano. Remember that when you’re strolling in the park! 

You will find three walking/hiking trails at the park: The 1-mile Red Trail, the 1.7-mile Green Trail, and the 3-mile Blue Trail. Once you reach the summit, you can have a spectacular view of Southeast Portland, the West hills, and the beautiful summer sunset if you’re on time. 

You can also have a view of the volcanic cinder cone, and if you’re there on the 3rd Saturday of August, you can get a chance to see the PDX Adult Soapbox Derby, where a large number of racers zoom down Mount Tabor.

Other activities at Mount Tabor Park include a basketball court, kids playground, volleyball and tennis courts, and an outdoor amphitheater. There’s also a dog park around the base of the hill, while you will find several picnic spots scattered randomly all over the park.

A Week In Portland, Oregon

Get Out and Explore A Weekend In Portland

As I said, there’s a lot to do in Portland, and just one weekend is not enough to visit all the places. However, I have put together some of the most popular places to visit in Portland for a weekend.

From exploring abandoned houses to sniffing your way through the prettiest rose garden and, of course, enjoying a picnic on lava cinders, you will indeed find the best things to do for a weekend in Portland in this extensive guide.

So, pack your bags, and put on some robust hiking boots, to experience all that Portland has to offer!

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