The Ultimate Weekend In Portland, Oregon Guide: Easy 2 Or 3 Day Itinerary!
Sitting on the Willamette River with the Pacific Coast to the west and Mount Hood to the east, you’ll find Portland, Oregon. The city surrounded by waterfalls and rainforests, is known for excellent dining and nightlife, outdoor activities, and of course, general weirdness.
Why is Portland so weird? Well I don’t know… Perhaps we should ask one of the participants of the World’s Largest Naked Bike Ride, or one of the leprechauns in the World’s Smallest Park, or maybe just ask one of the folks taking a photo of the carpet at PDX… you get my point?
Okay but seriously, alongside Portland’s “weird” is a friendly, beautiful city with much to enjoy.
Read on for what to do with a weekend in Portland, Oregon!
The Best Things To Do With Your Weekend In Portland, Oregon
Day 1: Weekend In Portland, Oregon
Voodoo Doughnuts
Be sure to visit this unique and quirky doughnut shop for a serious sugar rush to start off your weekend in Portland! Among the classics they have many unique options, such as an cereal covered doughnuts and voodoo dolls.
To visit the original location you’ll want to go to 22 SW 3rd Avenue. Be sure to stop by early, the line can get very long!
Note: You’ll hear many people debating whether Voodoo or Blue Star Donuts is better, do yourself a favor and taste test both.
“Keep Portland Weird” Sign
Part of visiting Portland is embracing the weird and celebrating the fun, quirky nature of the city that welcomes all characters.
Right across from the original Voodoo Doughnuts location is the iconic “Keep Portland Weird” sign. So while you’re in the area grab a coffee from Stumptown Coffee Roasters and snap a pic at the beloved mural!
The mural is located on the back of Dante’s at 350 W. Burnside St. in a parking lot viewable from 3rd Ave.
Powell’s City Of Books
Powell’s Books is the largest independent bookstore in the world. The four story building occupies an entire city block and has a cafe with lots of seating, a bookworms dream!
Wander the store and enjoy their vast selection of approximately 1,000,000 books. This is definitely one of the best places to find yourself when spending a weekend in Portland.
Tom McCall Waterfront Park & Willamette River
Tom McCall is a cherry blossom-lined, waterfront park used for recreation and pedestrian commuters alike. Take a walk along the Willamette River, enjoy a picnic, or visit the Oregon Maritime Museum if that suits your fancy.
The Willamette River is a core feature of Portland so it’s no surprise some of the most fun things to do in downtown Portland, Oregon occur on this body of water! Here you can kayak, go for a boat tour, even go in a submarine!
Tip: While you’re in the area snap a photo at the “White Stag” sign, AKA the “Portland Sign” and at Mill Ends Park which is the world’s smallest park!
Portland Saturday Market
If visiting on Saturday be sure to also check out the Portland Saturday Market! The open-air market offers over 250 stalls of local crafts and gifts as well as food and entertainment. Portland has tons of creative small businesses and this is a great way to check them out!
It’s open from March – Christmas Eve from 10 am – 5 pm.
If you’re not able to visit the market check out Portland’s many festivals and street fairs, check out Travel Portland’s event schedule.
Explore Portland International Rose Test Garden
The International Rose Test Garden is an absolute must if you’re spending a weekend in the City of Roses!
The garden was originally established in the early 1900’s by Jesse Currey who feared hybrid roses grown in Europe wouldn’t survive WWI. Today it’s the country’s oldest rose garden of this kind and attracts visitors from around the world.
The 4.5 acre garden is free and open daily.
If you’re not visiting April through October, when the roses are in bloom don’t worry there’s still loads of stuff to do in Washington Park.
Washington Park
The International Rose Test Garden is located in the Washington Park which is home to tons of Portland’s best attractions!
A few things worth checking out in Washington Park include:
- Portland Zoo
- World Forestry Center
- Hoyt Arboretum
- Portland Japanese Garden
Of course you can also walk, bike, picnic, or play games as you would in any other park, too!
Lan Su Chinese Garden
Want more gardens? Or looking for something on a smaller scale? Check out the Lan Su Chinese Garden in Old Town!
This is a peaceful botanical garden featuring rare plants native to China, decorative stonework and a tea shop.
The Lan Su Chinese Garden is a great place to stop for a quiet walk in downtown Portland!
Day 2: Weekend In Portland, Oregon
Sunrise At Pittock Mansion
Pittock Mansion is a historic home near Washington Park that happens to have some of the best city views. Sunrise is especially spectacular here so roll yourself out of bed during the wee hours, I promise this won’t disappoint.
The estate is open to the public with self-guided or guided tours available for purchase or you can simply walk the grounds for free.
Did You Know? This French Renaissance-style château was built in the early 1900’s and dedicated to the city of Portland in the 60’s.
You can drive to the mansion or take the popular 2.5 mile hike through Forest Park.
Forest Park & Macleay Park
If you enjoy outdoor activities this area has miles of trails worth exploring and is a great way to spend your morning!
While you’re here you’ll definitely want to explore the Witch’s Castle (also known as the Macleay Park Shelter or Witches Castle).
It’s an abandoned, graffitied two-story stone structure along the Balch Creek. Accessing the “castle” requires a little bit of a hike but it’s fairly easy. You’ll find the structure near the intersection of Wildwood and Lower Macleay Trail.
Visit A Museum
Portland has tons of great museums with tons of variety, I recommend picking one or two to explore during your weekend in Portland!
Popular Museums In Portland:
- Portland Art Museum
- Oregon Museum Of Science & Industry
- Oregon Historical Society
- Rice Northwest Museum of Rocks & Minerals
- World Forestry Center
- Oregon Jewish Museum and Center for Holocaust Education
- Oregon Rail Heritage Center
- Japanese American Museum of Oregon
Quirky Museums In Portland:
If you love odd museums you’ll have the best time in Portland! Check out some of these quirky displays you’ll only find in Stumptown.
- Stark’s Vacuum Museum
- The Freakybuttrue Peculiarium & Museum
- Ernest Starr Memorial Museum of Dental Anomalies
Looking for free things to do in Portland? Check out The Best Free Things To Do In Portland Oregon which includes a list of free museums in Portland!
Day 3: Weekend In Portland, Oregon
If you’re in Portland for a long weekend I highly recommend going for a day trip! There are so many beautiful places to explore near downtown!
Day Trips From Portland Oregon
Some of the best day trips from Portland are:
- Cannon Beach known for stunning, rocky coastline, you can’t go wrong with the Oregon Coast – 1.5 hours from Portland.
- Multnomah Falls, the tallest waterfall in Oregon – 30 minutes from downtown.
- Silver Falls State Park has one of the highest concentration of waterfalls in the country – located an hour from Portland.
- Columbia River Gorge, a stunning canyon reaching depths of 4,000 feet overlooking the Columbia River – 30 minutes to an hour from downtown Portland.
- Willamette Valley Vineyards known especially for high quality Pinot Noir! – 1+ hour from Portland.
Things To Do At Night In Portland, Oregon
Foodie Tour
Portland, Oregon is consistently named one of the top foodie cities in the United States, and for good reason! This small city boasts an impressive assortment of dining options with cuisines from all over the world.
Accessibility to farm-fresh produce, some wickedly creative chefs, and an abundance of adventurous diners are all factors which make Portland, Oregon one of the top foodie destinations in the US.
Go for your own tour our follow along with a guide for some of Portland’s best grub:
- Bike & Food Cart Tour
- “Restaurant Row” Tour
- Portland Pizza Tour
- Ice Cream Tour
- Brunch Food Tour
- Custom Food Tour
Vegan Foodie Tour
Vegans, rejoice! Portland is a plant-based mecca, there are countless options to choose from in just about any category of food you can imagine.
Portland has over 50 vegan-only restaurants, in a city with just over a half a million residents, that is pretty crazy and so exciting if you’re a plant-based foodie.
Go for a self-guided tour or schedule a professional tour with Forktown.
Food Halls & Cart Pods
In addition to tons of excellent restaurants in Portland there’s also hundreds of excellent food carts and trucks! Food halls and cart pods are a great way to support small business and indulge in all the delicious food.
Below are just a few of the most popular marketplaces and cart pods, but know there are many more!
- Prost Marketplace
- Hawthorne Asylum
- Portland Food Hall
- Cartopia
- Pine Street Market
- Cartlandia
Visit A Brewery
Craft beer drinkers will feel right at home in Portland! There are no shortage of breweries here, in fact, the area is home to over 80 of them!
Join an official tour, spend an afternoon brewpub hopping on your own, or just stop in for a pint after a long day of sightseeing. No matter which you do, you’ll be a happy beer drinker here in Portland.
Best Breweries In Portland, Oregon
There are many excellent breweries in the region but a few popular options are:
- Upright Brewing
- Breakside Brewery
- Deschutes Brewery
- Von Ebert Brewing
- Ex Novo Brewing Co.
If you love craft beer festivals be sure to check out Zwickelmania and Portland Craft Beer Festival, these are always some of the most fun events in downtown Portland, Oregon!
Want to go for a beer tour? Check out this Bike Brewery Tour or small group Bus Brewery Tour.
Catch A Show
On any given night here you’ll find local and national artists playing a vast variety of genres in venues throughout the Portland metro area. Whether you want to catch a sold out show at the Moda Center or Revolution Hall or tuck into an unsuspecting bar, there is something for any occasion here.
McMenamins Crystal Ballroom
The Crystal has been attracting music lovers and dancers for 100 years plus. From folk to jazz, and indie to soul this historic Portland music hall has seen it all.
The gorgeous building features high ceilings and grand chandeliers, a balcony, and floors that bounce… seriously.
The ballroom complex includes multiple rooms at varying sizes so you’ll be sure to find something you enjoy here!
Getting To Portland, Oregon
Portland International Airport – 20 minute drive to downtown Portland
At the airport be sure to check out the ugly carpet, it’s a thing.
From the airport arrange an Uber/Lyft, taxi, or rental car into downtown.
Tip: If you’re traveling from a city within the region check out the train schedule, Amtrak is a great option! This was our preferred method when traveling from Portland to Seattle.
Looking for cheap flights? Be sure to sign up for Going (formerly Scott’s Cheap Flights) to get cheap flight alerts delivered right to your inbox. It’s a free service I’ve used for years and couldn’t recommend more.
Where To Stay For Your Weekend In Portland, Oregon
Downtown and the Pearl District are great options for weekend visitors. The two areas are relatively small and border each other, so don’t stress too much about which is better.
Between these two areas you’ll find plenty of hotels and property rentals within walking distance of restaurants, breweries, and many other attractions.
We stayed downtown at Hotel Lucia, the location was perfect and allowed us to walk just about everywhere we wanted to go.
Some additional options include:
- The Clyde Hotel Portland
- Portland Marriott Downtown Waterfront
- The Nines
- Inn at Northrup Station
- The Paramount Hotel
- Moxy Portland Downtown
- Sentinel Hotel
- KEX Portland
Getting Around Portland
Unless you’re planning to leave the downtown area you don’t need a car. You can take advantage of public transportation, walking, biking (they have bike share programs such as Biketown), and the occasional Uber/ Lyft.
The downtown area is small so you’ll have no problem getting around.
If you plan to do day trips outside Portland you’ll either need a car or you can join a tour.
As you can see, there’s so much to do with just one weekend in Portland, Oregon! I look forward to returning and exploring more of the wonderful and weird the Portland area has to offer!
Any questions or additional ideas? Please leave a comment!
If you’d like to follow along with my travels in real time, check out @seen.by.amy on Instagram or @seenbyamy on TikTok!
Looking for more ideas? Below are additional Portland and Pacific Northwest guides or head on over to Travel Portland!
More Information For Your Portland, Oregon Vacation:
More Information For Your West Coast Travels:
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Amy! I have always wanted to see those falls you have in the picture. I’m going to put this on my bucket list!
It looks amazing, huh? Portland’s so beautiful.