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Hip, funky and fun, Portland, Oregon is a perfect weekend destination! Boasting abundant green space, cool urban districts and a fabulous foodie scene, travelers visiting Portland in a weekend can truly experience the city.
Our Portland Itinerary features the top highlights – and visitors to Oregon can use our outline to create their best weekend trip to the City of Roses!
Weekend in Portland Itinerary
Spending a weekend in Portland, Oregon is an excellent way to get acquainted with the city that proudly proclaims to be weird.
From peculiar sights to natural attractions, visitors will find there is plenty to do on a weekend trip to Portland.
Based on diligent research and experiences from several visits, we have created a 3-Day Itinerary Portland that is perfect for weekend trips!
About Our 3 Days in Portland, Oregon Itinerary
In our weekend trip planner, we outline a day-by-day plan for visiting Portland in 3 days.
It is assumed that you will arrive mid-afternoon on Friday (or Saturday) and stay until the evening on Sunday (or Monday).
Although our itinerary does include a few ‘weekend only’ events, those activities can easily be substituted for weekday adventures.
Therefore, this itinerary for Portland, Oregon can really be used for a trip over any days of the week!
Portland Weekend Itinerary
In this article, we have outlined how to spend 3 perfect days in Portland. In addition to our plan for a weekend trip to Portland, Oregon, we also include a useful map of attractions and essential tips.
Pin, Save or Bookmark our Portland Travel Guide to plan your Trip to Oregon!
Day 1 of Your Portland Weekend Trip
Begin your Portland 3-Day Itinerary by get settled into your accommodations (suggestions below), then set out to discover one of the city’s most vibrant districts, Pearl.
Pearl District
The Pearl District is an absolute must in every Portland, Oregon vacation itinerary! Once the warehouse district, the Pearl has evolved into a stylish enclave of residences, art galleries, green parks and some fabulous restaurants.
Powell’s City of Books
Start your exploration of the Pearl District at the landmark Powell’s, which is the largest independent bookstore in the world. The massive space covers an entire city block and ranks on many lists of Top Bookstores in America.
Things To See in Portland Pearl
After perusing the literature, take a stroll through North Park Blocks, a green urban oasis since 1869.
Next, walk north on 11th Ave – the best street in Pearl District – passing boutique shops, cafes and restaurants along the way.
Stride through Jamison Square, which features fountains where you can cool your feet in the summertime, then walk through the wetland habitat on the raised boardwalk in Tanner Springs Park.
At The Fields Park, hop on the Willamette River Greenway Trail and make your back south to Chinatown and Old Town Portland.
Discover Old Town Chinatown Portland
Although not as impressive as San Francisco – there is an ornamental gate at NW 4th Ave and W Burnside St.
The real highlight of the area is the lush Lan Su Chinese Garden. Other attractions are the Steel Bridge (a double-decker bridge built in 1912) and Union Station (built in the late 1800s and is listed on the National Register of Historic Places).
Portland Underground Tunnel Tour
The Shanghai Tunnels are a fascinating place to see in Portland. Guided tours depart multiple times a day, taking visitors into the subterranean space to learn about history of the tunnels and the ghosts that reside in them. Book it!
Ground Kontrol Classic Arcade
Ease into the evening with a barcade experience at the vintage Ground Kontrol. Patrons can play their favorite retro games while sipping a beer. It’s the best place in Portland to get your pinball on!
Dinner, Drinks and Live Music in Portland, OR
There are many different ways to spend the first night of your Portland weekend. Where you end up will likely depend on your style and mood.
Personally, we believe the PNW craft beer scene is not to be missed. However, downtown PDX has stellar dining options – especially on the rooftop perches above the city.
Additionally, there are historic spots, cozy corners, international eats and plenty of live music. We are highlighting a few of the best places to go in Portland, OR on your first night.
Portland Craft Beer
Nicknamed ‘Beervana,’ Portland boasts an astounding number of breweries. Getting a taste of locally produced brew is practically essential during your 3 days in Portland.
The Pearl District is home to a range of restaurants and some of the best breweries in Portland. Among the many, our favorite spot is Deschutes Brewery and Public House. The menu is elevated pub grub and the 26 brews on tap are always fresh and tasty!
Brewery Crawl and Cocktail Hop in Portland
From Deschutes, visitors can create their own Portland brewery tour, making stops at 10 Barrel Brewing, Backwoods Brewing Company and Old Town Brewing.
Looking for a fun activity for your girls’ or guys’ weekend in Portland? Discover great craft beer and meet fellow travelers on a pub tour!
Not a fan of beer? No problem! For handcrafted cocktails, try Teardrop Lounge, Fools and Horses or Abigail Hall.
Eat and Drink with a View in Portland
Travelers who would rather include fine dining and fancy cocktails in their Portland vacation have some superb options, too.
Portland City Grill is an exceptional spot that offers 360-degree views from the 30th floor of the US Bancorp Tower. For after dinner drinks and city lights, head up to one of the best Portland rooftop bars – like Departure or XPORT.
Historic and Cozy Vibes
Dating to 1879 and boasting a unique ambiance, Huber’s Cafe is one of the best places to eat on a 3-day weekend in Portland.
From the popular roasted turkey dinners to their famous Spanish coffee, Huber’s is a good choice for happy hour, dinner or a late night snack.
After a meal, head for the cozy but chic Multnomah Whiskey Library. Here bottles line the shelves along exposed brick walls and leather chairs face a roaring fireplace.
Tea and International Fare
Portland might be boozy, but you certainly don’t need to drink in alcohol to have a good time in this city!
Start with a late afternoon tea flight at Smith Teamaker or Behind The Museum Cafe. Then indulge in international fare at one of the best Asian restaurants in Portland. Top picks are Thai Peacock, Masu Sushi or Luc Lac Vietnamese Kitchen.
Portland Live Music
If live music is your jam, check out who is playing at the historic McMenamins Crystal Ballroom, which has seen a slew of acts grace its stage since the early 1900s.
Alternatively, see what is happening at The Armory Theater (aka Portland Center Stage) for an intimate performance. Just don’t stay out too late, because tomorrow is another full day of fun!
Day 2 of Your Portland Itinerary
Start with some classic food experiences, then see more city center Portland sights. End the day across the Willamette River exploring the distinctly different districts in East Portland.
Stumptown Coffee Roasters
The city’s coffee craze is serious business – and Stumptown Coffee is the place to experience it. A local Portland favorite since 1999 (although now owned by Peet’s), Stumptown embodies the Third Wave Coffee Movement.
Voodoo Doughnut
In 2000, Voodoo opened in Portland, OR…and so the doughnut craze began. With a line of creative flavors – like Bacon Maple Ale – the shop quickly made headlines.
Their Portland Cream Doughnut has been proclaimed the city’s official doughnut. Who ever knew there was such a thing?
Patrons line up out the door and down the block everyday for the sugary treats – and when in Portland, go on and join the crowd!
More Portland Donuts
Donut connoisseurs will want to check out Blue Star as well. Their gourmet donuts include flavors like Blueberry Basil Cake and Mexican Hot Chocolate.
For different donut experience, make your way to Pip’s Original Doughnuts and Chai. The old-fashioned shop will likely have a line, but the freshly fried donuts are melt-in-your-mouth delicious. Oh – they taste best with a flight of chai teas!
Pro Tip: If you really want to go crazy, join a guided Donut Tour during your three days in Portland, Oregon.
Portland Saturday Market
Recognized as the longest running outdoor arts-and-crafts bazaar in the US, the Saturday Market is a must-see on your weekend getaway to Portland, Oregon.
Opened in 1974, the free outdoor market features nearly 400 local vendors. Plus, there is live music and heaps of international food truck options.
Pro Tip: Wander under the Burnside Bridge where you have the best view of the famous neon White Stag Sign – a must-see in Portland.
Downtown Portland Tours
Cycling is a popular Portland trip idea. In the afternoon, hop on two wheels for a guided bike tour of Portland downtown attractions.
Sights on the route includes Pioneer Courthouse Square, Tom McCall Waterfront Park and Fifth Avenue Food Cart Pod. Find out more!
Alternatively, visitors interested in learning more about the foodie scene can join a Portland Food Tour.
This small-group walking tour includes multiple stops at some of the best Portland food carts. This excursion is limited to just 10 people. Reserve your spot!
Explore Portland’s Eastside
Now midway through your Portland travel itinerary, cross the Willamette River to explore some of the other fun areas of the city.
Buckman District
Delve into the Buckman Neighborhood. If you need a late afternoon pick-me-up, stop at Rimsky’s. This eclectic (and some say haunted) coffeeshop located in an old Victorian style house.
Next, if you want to stay on theme, take a walk through nearby Lone Fir Cemetery, an enchanting final resting place for many of the city’s most prominent citizens.
If the weather is cooperating, make your way to Eastbank Esplanade and Audrey McCall Beach. The green belt is a great place to stretch your legs and provides super views of the Portland skyline.
Hawthorne Blvd
Hawthorne is one of the coolest places to visit in Portland, Oregon. True to the spirit of the city, this street is home to an array of hip shops, independent retailers and eclectic eats.
Visitors can dig for vintage threads at House of Vintage, Magpie or Red Light Clothing Exchange. For more nostalgic shopping, stop by the local family-run Excalibur Comics or search for vinyl at Jackpot Records and Tomorrow Records.
Pro Tip: Those who prefer to spend the entire day in East Portland can skip downtown sightseeing and start with brunch at Jam on Hawthorne!
Mount Tabor
This little park was once a volcano, but now provides incredible views on clear days. Take one of the numerous paths that weave through the forest and around the reservoir to get to the top of Mt Tabor.
East Portland Evening Out
The city’s east side districts are a fun and vibrant place to delve into for a night of food, drinks and entertainment.
Spend an Evening in Buckman
If you want to eat dinner in Buckman, stay on Hawthorne Street – which hosts numerous restaurants. The eateries range from fine dining to farm fresh to funky fare.
Our favorite spot for a meal in Buckman is the Cartopia Food Carts. Located on the northwest corner of the Ladd’s Addition neighborhood, this food cart pod offers a variety of delicious fare. We suggest getting a bite from multiple vendors for a complete Portland foodie experience!
Still hungry? No shame! Venture around the corner to Asylum Food Carts and get a savory Dutch-themed waffle sandwich from Smaaken.
Another popular dining establishment on Hawthorne is Por Que No. This popular Mexican eatery serves unbelievably good tacos and refreshing margaritas.
Buckman Brewery Hop or Patio Cocktails
After dinner, sample more craft beer hopping from brewery to tap room in Buckman. Rogue Eastside Pub, Grand Fir Brewing and Lucky Labrador Brew Pub are a few of the many Buckman brewery tap rooms.
Alternatively, sip cocktails at Rontoms – a laid-back spot with live music and good food. Plus, they have a patio with picnic tables and ping pong!
Dinner and Drinks in Division
On the other hand, go a bit further south to Division, where you can feast on famous burgers at PDX Sliders.
Then, attend the Saturday midnight showing of The Rocky Horror Picture Show at Clinton Street Theater.
North Mississippi Avenue and Alberta Arts District
Shops, restaurants, bars and theaters line the festive five-block stretch of North Mississippi Avenue in the historic North Portland neighborhood of Humboldt.
Nearby, the Alberta Arts District is another area that is bustling with restaurants, bars and culture. Go underground to Les Caves Wine Bar, make your own Bloody Mary in a converted gas station at Radio Room or check in on Great Notion Brewing.
More Evening Portland Entertainment Options
Eating and drinking isn’t the only way to spend a night out in Portland. The city is well-known for it’s theater shows and sports teams.
McMenamins Bagdad Theater and Pub is a renovated 1927 movie house and the Hawthorne Theater is a fun performance venue with a wide variety of acts.
Sports enthusiasts can catch a Portland Trail Blazers game at Moda Center or join the ‘Army’ of Portland Timbers fans for a match at Providence Park.
Day 3 of Your Portland Weekend Itinerary
Wrap up your Portland, Oregon weekend spending time in the beautiful outdoors. Then visit more cool districts and end the day at a renovated schoolhouse.
Pine State Biscuits for Breakfast
This modern diner excels at hearty, home cooked meals that are downright good. Go for the rich and decadent Reggie Deluxe sandwich on a fresh made biscuit (but expect a line to get it).
Outdoor Portland Activities
The nature surrounding this city is astounding! Lush and green, savoring these outdoor spots is one of the top things to do in Portland in 3 days.
Washington Park, Portland Rose Garden and the Japanese Garden
A public green space the 1870s, Washington Park is a 410-acre site featuring several attractions – and visiting it is a must on your Portland, Oregon itinerary!
In addition to 15 miles of hillside trails, top attractions include the Oregon Zoo, Hoyt Arboretum, the International Rose Test Garden and the exceptional Portland Japanese Garden.
The Redwood Observation Deck, memorials, statues, museums and playgrounds are more Washington Park highlights.
Forest Park
West of Washington Park, visitors can hit the trails in the even larger Forest Park. The urban hillside overlooks the Willamette River and features 70 miles of walking paths.
Rather than tackling the trails on your own, join a local guide for a hike on the best trails to the top sights. Get the details!
Discover NW 23rd
After trekking through the parks, if you want to spend the entire day in the area, aim for NW 23rd Avenue. Wander through the quaint Northwest District and eat lunch at Nob Hill Food Carts.
Afterwards, go to the interactive and entertaining Freakybutture Peculiarium, which is a fantastic place for funny photo ops and getting a little weird in Portland!
Willamette River Boat Rides
Alternatively, get out on the river! A tributary of the Columbia River, the Willamette flows right through the heart of Portland.
One of the top options for river activities is taking a Willamette Jet Boat ride. There are different tours to choose from – like Willamette Falls, the Shipyards or a quick scenic sprint along the waterfront and under bridges. These absolutely thrilling rides guarantee that passengers will get wet, so be prepared for that!
An alternate option is to travel by jet boat on a 3.5 hour trip under Portland bridges and up the Columbia River to see Multnomah Falls. If a soppy speedboat ride isn’t your style, opt instead for a relaxing Lunch Sightseeing Cruise.
East Portland Outdoor Parks
If you still have time in your Portland vacation itinerary (or if this is not your first trip to Portland), consider exploring an extinct volcanic cinder cone and an interesting grotto.
The Rocky Butte Natural Area is an excellent neighborhood park. The extinct volcano features a gorgeous lookout point that is definitely worth including in your 3 Days in Portland Itinerary. If you get a clear day, the elevated Rocky Butte Park peak offers stellar views of Mount Hood.
Nearby, The Grotto is another fantastic place to see. The National Sanctuary of Our Sorrowful Mother is an outdoor shrine that dates to 1924. Today, visitors come to celebrate mass, walk the beautiful gardens and in December revel at the Christmas Festival of Lights.
McMenamins Kennedy School
Spend the last few hours of your Portland 3 Day Itinerary at the McMenamins Kennedy School. Don’t worry – you won’t be sitting in a boring classroom!
McMenamins is an Oregon brand that is known for renovating historic buildings and transforming them into truly spectacular venues – and Kennedy School is one of the best. In addition to the multiple bars and pool, the property is also a hotel.
Those with a car might want to travel further afield to the McMenamins Edgefield property. Located in Troutdale (at the beginning of the historic driving route to the Columbia Gorge Waterfalls), Edgefield is a 74-acre entertainment hub, inclusive of a hotel, winery, distillery, brewery, restaurants, pool, theater, golf and gardens!
More Things To Do in Portland, Oregon
We have highlighted the best things to do for your Portland Itinerary 3 Days trip. However, we also suggest checking out some museums or embarking on a day trip from Portland, Oregon.
Portland Museums
If foul weather keeps you from being outdoors, don’t despair! There are plenty of cool places to see in Portland that are indoors.
OMSI
The Oregon Museum of Science and Industry is one of the best museums in Portland. Featuring interactive and engaging science-based displays, the venue is family friendly (but appeals to visitors of all ages).
The Pittock Mansion
Located just north of Washington Park, Pittock Mansion was built in 1914. Today, visitors can tour 23 rooms decorated in period pieces. Plus, the garden has a phenomenal viewpoint (which can be visited for free).
The Oregon Historical Museum
The Oregon Historical Society Museum delves into the history of the land and people – tracing it from pre-historic to modern times.
The Portland Art Museum
Displaying a fine collection of artwork from around the world, the Portland Art Museum has both a permanent collection and rotating exhibits.
Portland Views from Above
Throughout our Portland Three Day Itinerary, we featured some of the best viewpoints in the city – but there are two more we want to highlight.
Portland Aerial Tram
On a clear day, there may be no better view than from the OHSU viewpoint. That said, getting there via gondola is half the fun!
Transporting passengers from the South Waterfront to the hillside Oregon Health and Science University hospital campus, the aerial tram takes just 4 minutes to ascend to the top.
For a group experience, join a guide for sunrise from the viewpoint – along with craft coffee and donuts. Get the details!
Portland Airplane Tour
Want an even better way to see Portland sights than from above? Visitors can take a short, scenic plane ride to view Portland from a truly unforgettable vantage point. Book it!
Portland Day Trip Options
Taking a day trip is an excellent way to see more of the stunning region. We are featuring a few of the highly-touted excursions from Portland.
Multnomah Falls and Columbia River Gorge
If you have a car, use our detailed Guide To Columbia River Gorge. We share the absolute best way to see the waterfalls on a Portland road trip.
If you want to leave the driving to someone else, consider a highly rated half-day tour. A guide offers interesting information about Oregon, while participants take in breathtaking vistas along the scenic byway.
Alternatively, choose from a morning or afternoon bike ride adventure tour of Columbia River Gorge. Find out more!
Willamette Valley Wine Tasting Tour
Spend the afternoon visiting 3 incredible wineries in the picturesque Willamette Valley. This small-group tour features transport by minivan (and pick up/drop off at downtown hotels) and wine tastings at all three stops. Get details!
Oregon Coast Tour from Portland
The Pacific Coastline in Oregon is a magnificent sight! We actually recommend taking a few days to complete the route – which you can read about in our complete guide to an Oregon Coastal Drive.
Those short on time can still get a glimpse of the coast on a full-day tour. This Portland day trip itinerary includes incredible scenery from Cannon Beach, Ecola State Park and Oswald West State Park. Learn more!
Vancouver, Washington
Just north across the Columbia River is the city of Vancouver, WA – and it’s a fabulous place to explore during your 3 Day Weekend in Portland.
The city feels more like a small town and is often referred to as a suburb of PDX. The area offers a fantastic waterfront, a handful of interesting sights and a buzzing craft beer scene. Use our tips for Things To Do in Vancouver, WA to plan your day!
Crater Lake National Park
Many visitors are tempted to squeeze a road trip to Crater Lake into a weekend Portland itinerary. Honestly, we think the 4-hour drive each way is too long during a quick visit.
That said, if you are planning a longer trip to Oregon and need additional Portland vacation ideas, Crater Lake can be a fabulous option.
Portland Oregon Map
Use this Google Map to find your way to all the best things to do in Portland, Oregon.
Travel Tips for Your Portland Itinerary
Now that you know what to do in Portland in a weekend (or longer), we have some final honest advice for your trip.
Organizing Your Portland 3 Day Trip
As you plan a trip to Portland, Oregon, staying organized it key. Our Trip Planning Printables are perfect for making sure nothing falls through the cracks!
How To Get to Portland, Oregon
The Portland International Airport is the main airport in Oregon. PDX is well-connected via public transport, but private ground transportation is also available and should be booked in advance.
When buying plane tickets, we start our search for the lowest airfare on SkyScanner – just be sure to follow our detailed Tips for Booking Flights.
Do You Need a Car in Portland, Oregon?
For our Weekend in Portland Itinerary, it is not necessary to rent a car. The city has an exceptional network of public transportation – including TriMet Bus and MAX Light Rail.
Uber is also available as well as Lyft. Plus, it’s fairly easy to get around Portland on foot, scooter and by bicycle.
Additionally, visitors can get to top Portland attractions on the Hop On Hop Off Pink Trolley. It makes stops at all the best sights in Portland, and provides live on-board commentary and an open-air seating area.
Where To Stay in Portland, Oregon
We believe the ideal place to stay is close to all the best Portland, Oregon sights to see.
The Paramount Hotel
We have stayed in various properties on our trips to Portland – and can personally recommend The Paramount Hotel.
Located in the heart of downtown, they offer clean rooms, comfy beds, an on-site restaurant, and sincere staff – all at an affordable price. Check availability!
Benson Hotel
We have yet to stay at the Benson, but it is an iconic hotel in the Portland city center. Top features are the elegant rooms and attentive service. Check rates!
Read our Tips for Booking Hotels to ensure you get the best value!
What To Pack for Your 3 Day Portland Itinerary
It’s finally time to pack for that Portland vacation. Grab your FREE Packing Checklist and let’s get to Oregon!
Walking Shoes
We cover a lot of ground in Portland for 3-Days! We recommend wearing a pair of comfortable walking shoes. I like these trainers from New Balance and Kris prefers Merrell trail shoes.
Portland Weather Appropriate Clothing
While summer days in Portland can be hot, nights will still be cool. We recommend packing clothes that can be layered. Extra layers are also essential if going on a boat tour or into the Oregon mountains.
Remember to bring a wide brimmed hat, good sunscreen and insect repellent, too. In the non-summer months, it is ideal to have a packable raincoat and a travel umbrella!
Travel Camera
Rather than relying on your phone, we suggest using an actual travel camera. We shoot with a Canon Rebel and a 18-135mm lens. This set-up comes bundled with all kinds of fun accessories, making it a perfect budget camera for budding photographers!
Day Bag
Whether you travel with a backpack or a suitcase, for long days of Portland sightseeing you will also want a great day pack to organize and secure all of your everyday items!
Start planning your US Trip! Search for the lowest airfares, the best accommodations and fun things to do…then start packing! Want more advice? Head over to our Travel Planning Page for tips on traveling – and for country-specific information, take a look at our Travel Guides Page!
PNW Travel Guides
The Pacific Northwest ranks as one of our favorite places to visit in the United States – and we have heaps of tips for fellow travelers!
- What To See in Seattle in 3 Days
- Things To Do in Spokane
- Why Visit Florence, Oregon (hint: the best Central Oregon Coast Hikes)
- What To Do in Bend, Oregon
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