Portland Itinerary A Perfect Weekend in Portland, Oregon by JetSettingFools.com

Portland Itinerary: Plan a Perfect Weekend in Portland, Oregon

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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 best of the city. Our Portland Itinerary features the top highlights – and visitors to Oregon can use our outline to create their Best Weekend in Portland trip plan!


Weekend in Portland Itinerary

Spending a weekend in Portland, Oregon is an excellent way to get acquainted with the city that so proudly proclaims to be weird. With a relaxed atmosphere and creative culture, visitors can get a good feel for Portland even in a short amount of time. From peculiar sights to natural attractions, visitors will find there is plenty to do on a weekend trip to Portland.


Planning a Portland Weekend Itinerary

On my first weekend trip to Oregon (and my very first time to the Pacific Northwest), I traveled to Portland to visit my cousin. Being in the company of a local, I wasn’t tasked with creating my own Portland, Oregon itinerary; she knew all the best places to go and had insider secrets. On that trip, I spent two days in Portland – and absolutely fell for the city.

Not long after my initial trip, I was itching to go back to discover even more. My cousin had since moved, so I took on the complete responsibility to plan a trip to Portland, Oregon from beginning to end. Intent on expanding my exploration, I created fun weekend trip itineraries that included the must see Portland sights, beautiful nature and the best food.

Based on diligent research and my experiences from several visits, we have created a 3-Day Itinerary Portland that is perfect for weekend trips!


3 Days in Portland, Oregon Itinerary: A Long Weekend

In our weekend trip planner for Portland, 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 Portland weekend itinerary does include a few ‘weekend only’ events, those activities can easily be substituted for weekday Portland adventures.

Therefore, this itinerary for Portland, Oregon can really be used for a trip over any days of the week!


A Longer or Shorter Trip to Portland, OR?

Furthermore, we understand that not all travelers are planning a Portland, Oregon 3-Day Itinerary. Some visitors are limited to just one day in Portland, while others may be creating a 5-Day Portland Itinerary.

To help fellow travelers, we offer suggestions for alternate Portland trip itineraries at the end of the article. Whether you are planning to see Portland in a day or are devising a longer Portland trip itinerary, you can use our tips to plan your ideal vacation to Oregon.

Looking for more to do in OR State? Use our guide to the Best Things To Do in Oregon

How To Spend a Perfect Weekend in Portland, Oregon by JetSettingFools.com


Weekend in Portland Itinerary

View of Winter in Portland, Oregon, United States of America

In our trip plan, we have outlined how to spend 3 perfect days in Portland. In addition to our day-by-day plan for a weekend trip to Portland, Oregon, we also include a useful map of attractions and essential tips – like how to get there, where to stay, when to visit Portland and what you will need to pack. 

Save, Bookmark or Pin our Portland Travel Guide to plan your trip to Oregon!


Day 1 Of Your Portland Weekend Trip

On Day 1 of your Portland 3-Day Itinerary, get settled into your accommodations (suggestions below), then set out to discover one of the city’s most vibrant districts, Pearl.

How To Plan a Weekend in Portland Oregon by JetSettingFools.com


Pearl District Portland

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 Portland restaurants.


Powell’s Bookstore

Start your exploration of the Pearl District at the landmark Powell’s City of Books, which is the largest independent bookstore in the world. The massive bookshop covers an entire city block and ranks on many lists as one of the Top 10 Bookstores in America.


Things To See in Portland Pearl District

After perusing the selection of books, take a walk through North Park Blocks, a green urban oasis since 1869. 

Make your way through the Pearl District, walking north on 11th – the best street in Pearl District – passing boutique shops, cafes and restaurants along the way. Walk through Jamison Square, which features fountains where you can cool your feet in the summertime, stroll through the wetland habitat on the raised boardwalk in Tanner Springs Park. 

At The Fields Park (which has a great play area for visitors planning a Kid Friendly Portland Itinerary), hop on the Willamette River Greenway Trail and make your back south to Chinatown and Old Town Portland. 


Discover Old Town Chinatown Portland

Make your way into the Old Town Chinatown District. Although not as impressive as other American Chinatown districts – like San Francisco – there is an ornamental gate (at NW 4th Ave and W Burnside St) and a handful of other sights to include in your Three Days in Portland Itinerary.


Things To Do in Portland Chinatown

The highlight of Chinatown – and one of the absolute best things to do in Portland – is the lush Lan Su Chinese Garden.

Other attractions in the district to add to your Portland Itinerary are the Steel Bridge (a double-decker bridge built in 1912) and Union Station (the city’s main transportation hub, which was 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 during your weekend in Portland. The guided tours depart multiple times a day, taking visitors into the subterranean space to learn about the history of the old tunnels and the ghosts that reside in them. Book it here!


Ground Kontrol Classic Arcade

Ease into the evening with a barcade experience at the classic Ground Kontrol Arcade. Patrons can play favorite retro games while sipping a beer. It’s the best place in Portland to get your pinball on! 


Evening Entertainment: Dinner, Drinks and Live Music in Portland OR

There are many different ways to spend the first night of your Portland weekend – so where you end up will depend on your style and mood. 

Personally, we think the PNW craft beer scene is not to be missed. However, downtown PDX has a stellar dining scene – especially in 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 claims to have more breweries than any other city in the world – so getting a taste of locally produced craft beer 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 favored spot is Deschutes Brewery and Public House – for both food and craft beer. The menu is elevated pub grub and the fresh beer – of which there are 26 brews on tap – is exceptional.


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 Von Ebert Brewing. For handcrafted cocktails, try Teardrop Lounge and Abigail Hall.

Looking for a fun activity for your girls’ or guys’ weekend in Portland? Discover the best craft beer on a mid-day craft beer tour


Dinner and Drinks with a View in Portland 

Travelers who would rather include fine dining and fancy cocktails in their Portland Itinerary have some superb options, too. 

Portland City Grill is an exceptional restaurant that offers 360-degree views from their 30th floor location in the US Bancorp Tower. In fact, if you arrive early enough, you can partake in the phenomenal happy hour specials – all while enjoying the panoramic views over Portland.

For after dinner cocktails and city lights, head up to one of the best Portland rooftop bars – like Departure Bar, XPORT or Tope (where they also have excellent tacos!). 


Historic and Cozy Vibes

One of the best things about spending a 3-day weekend in Portland is the quirky and cool establishments that dot the cityscape – and Huber’s Café is one of them. 

Dating to 1879 and boasting a unique ambiance, Huber’s is one of the best places to eat 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, where bottles line the shelves along exposed brick walls and leather chairs face a roaring fireplace. 


Tea and International Fare

Portland might be famous for beer, but you certainly don’t need to drink in Portland to have a good time. 

Start with an early evening tea flight at Smith Teamaker, then indulge in international fare at one of the best Asian restaurants in Portland. Top picks are Thai Peacock Restaurant, 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 and entertaining performance. Just don’t stay out too late, because tomorrow is another full day of fun! 


Day 2 Of Your Weekend in Portland Itinerary

On the second day of your Three Days in Portland Itinerary, start with some classic Portland food experiences, then see Downtown Portland sights. End the day across the Willamette River exploring the distinctly different districts in East Portland.

How To Spend 3 Days in Portland Oregon by JetSettingFools.com


Stumptown Coffee Roasters

The city’s coffee craze is serious business – and Stumptown Coffee is the place to experience it on your weekend in Portland, Oregon. A local Portland favorite since 1999 (although now owned by Peet’s Coffee), Stumptown embodies the Third Wave Coffee Movement. 


Voodoo Doughnut Portland

In 2000, Voodoo Doughnut 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 and 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 breakfast treats – and on your weekend in Portland, you should join the crowd!


More Portland Donuts

Visitors who don’t want to stand in line, but still want a darn good doughnut, might want to check out Blue Star Donuts instead (although there are sometimes lines here as well). Their gourmet donuts include flavors like Blueberry Basil Cake and Mexican Hot Chocolate.

However, for a classic donut experience, make your way to Pip’s Original Doughnuts and Chai. The old-fashioned donut shop will likely have a line, but it’s worth it for the freshly fried donuts that are melt-in-your-mouth delicious. Oh – and they taste best with a flight of chai teas! 

Pro Tip: If you really want to go crazy, try donuts from multiple spots. Or, better yet, join a guided Donut Tour during your three days in Portland, Oregon.


Portland Saturday Market

Recognized as the longest running outdoor arts-and-crafts market in the US, the Portland 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 always live music and heaps of international food truck options.

Pro Tip: Wander from the market north under the Burnside Bridge where you have the best view of the famous neon White Stag Sign – a must-see Portland, Oregon landmark. (Look for it on the north side of the bridge on Couch Street). 


Downtown Portland Bike Tour

Cycling is a popular mode of transport in the city – which is why taking a spin on two wheels is one of our top Portland trip ideas.

In the afternoon, hop on a bicycle for a guided tour of Portland downtown attractions and districts. Biking is one of the best ways to get around Portland – and on the tour, you can learn more about the city’s history as you pedal through the streets. Portland sightseeing on the route includes Pioneer Courthouse Square, Tom McCall Waterfront Park and Fifth Avenue Food Cart Pod. Find out more!


Another Popular Portland Tour

Alternatively, visitors interested in learning more about the food culture can add a Portland Food Tour to their Portland 3 Day Itinerary. The small-group walking tour includes 5 food stops at some of the best Portland restaurants and food carts. This tour is limited to just 12 people, so reserve your spot in advance!


Explore a Fascinating District in Portland’s Eastside 

By mid-afternoon of your second day of your Portland travel itinerary, cross the Willamette River to the east side of Portland to explore some of the best districts. 


Buckman District

Delve into the Buckman Neighborhood, a foodie haven and craft beer paradise that you shouldn’t miss on your Portland Weekend itinerary.

If you need a late afternoon pick-me-up, stop at Rimsky’s – an eclectic (and some say haunted) cash-only 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 Portland’s most prominent citizens.


Hawthorne Street

Hawthorne is one of the coolest places to visit in Portland, Oregon. True to the spirit of the city, there street is home to an array of hip shops, independent retailers and eclectic eats. 

Pro Tip: Travelers who want to spend the entire day in East Portland can skip downtown sightseeing and start with brunch at Jam on Hawthorne, one of the best places to eat breakfast in Portland. Then, with a full belly, begin a full day of shopping along Hawthorne!


Hawthorne Street Vintage Shopping

Visitors can dig for vintage threads at House of Vintage, Village Merchants, 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. 


Mount Tabor

The east side of Hawthorne ends at Mount Tabor. The little park was once a volcano, but now provides incredible views. Take one of the numerous paths that weave through the forest and around the reservoir to get to the top of Mt Tabor. 


An Evening Out on Day 2 of Your Portland Weekend Trip

The city’s east side districts are a fun and vibrant place to delve into 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, in addition to being lined with vintage stores and boasting heaps of character, also hosts numerous restaurants. The eateries range from fine dining to farm fresh to funky fare.

That said, our favorite spot for a meal in Buckman is the Cartopia food cart pod. Located on the northwest corner of the Ladd’s Addition neighborhood (one of the oldest planned neighborhoods in Portland), the Cartopia food cart pod offers a variety of delicious fare. We recommend getting a bite to eat 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 – that is not a food truck – is Por Que No – a popular Mexican eatery serving unbelievably good tacos and refreshing margaritas. (Numerous Portland locations if you’re full!).


Buckman Brewery Hop or Patio Cocktails

After dinner, sample more Portland craft beer as you bar hop from brewery to tap room in Buckman. Cascade Brewing Barrel House, Grand Fir Brewing, Lucky Labrador Brew Pub and Away Days Brewing Company are a few of the favorite Buckman brewery tap rooms. 

Alternatively, sip cocktails at Rontoms – a laid-back restaurant with live music and good food. Plus, they have a patio with picnic tables and ping pong. 

The Goodfoot – with a basement live music venue and an upstairs pub – is a fun place for nightlife in Buckman.


Dinner and Drinks in Division

On the other hand, you could leave Buckman and go a bit further south to Division, where you can feast on famous burgers at PDX Sliders – which many say is a Portland, Oregon Itinerary must-do!

Then, attend the Saturday midnight showing of The Rocky Horror Picture Show at Clinton Street Theater.

Top Tip: Pok Pok – and specifically their fish sauce wings – were long a staple on Division Street, but they have sadly closed their doors.


A Night on North Mississippi Avenue or in 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 in Portland, OR that is bustling with restaurants, bars and culture. Go underground to Les Caves Wine Bar, drink a divine Bloody Mary in a converted gas station at Radio Room or sip local craft beer at 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 district movie theaters that show Indie films – plus there are heaps of stages where visitors can catch a major production or independent play. Plus, Portland is home to numerous professional sports teams.

McMenamins Bagdad Theater and Pub is a renovated 1927 movie theater and the Hawthorne Theater is a fun performance venue with a wide variety of acts.

Sports enthusiasts can catch a game when visiting Portland. The NBA Portland Trail Blazers play at Moda Center, just across the Willamette River from downtown or you could join the ‘Army’ of Portland Timbers fans for a MLS soccer match at Providence Park. Numerous other teams (like the collegiate baseball Portland Pickles and the junior ice hockey Portland Winterhawks) play at various times throughout the year.


Day 3 of Your Portland Weekend Itinerary

On Day 3 of your weekend in Portland, Oregon you will see more of the best attractions. Spend time in the beautiful outdoors (or use our tips in the next section for rainy day museums), visit more cool districts and end the day at a renovated schoolhouse. 

3-Day Portland Itinerary by JetSettingFools.com


Pine State Biscuits for Breakfast

Start the final day of your weekend in Portland at a local hot spot: Pine State Biscuits. The 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 long line to get it).


Outdoor Portland Activities

The nature surrounding the city is astounding! Lush and green, spending time at 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 city park since the 1870s, Washington Park is a 410-acre park featuring several attractions – and visiting is a must on your Portland, Oregon itinerary!

In addition to the 15 miles of hillside, forested trails, the top park 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 park overlooks the Willamette River and features 70 miles of trails. Enthusiastic trekkers can make a detour to walk across the historic St. Johns Bridge. 

Rather than tackling the trails on your own, visitors can join a local guide for a hike on the best trails to the best sights – including the International Rose Test Garden, the Japanese Garden and the Witch’s Castle. Get more 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 a hip local restaurant – or dine at the charming Nob Hill Food Carts.

Afterwards, go to the interactive and incredibly entertaining museum, The Freakybutture Peculiarium and Museum, which is a fantastic place for funny photo ops and getting a little weird in Portland!

Walk along NW 23rd popping into boutique shops and galleries – and then cool down with ice cream from Salt and Straw, an artisan Portland-based ice creamery featuring unique flavor combinations.


Willamette River Boat Rides

Alternatively, get out on the river! A tributary of the Columbia River, the Willamette River flows right through the heart of Portland and is fun for outdoor recreation. One of the top Portland vacation ideas for river activities is taking a Willamette Jet Boat ride.

There are different jet boat tours to choose from – like Willamette Falls, the Shipyards or a quick scenic sprint along the waterfront and under bridges. The rides – which are absolutely thrilling – 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. Book it here!

If a soppy speedboat ride isn’t your style, opt instead for a relaxing Lunch Sightseeing Cruise for your Portland weekend itinerary.


East Portland Outdoor Parks

If you still have room in your Portland vacation itinerary (or if this is not your first trip to Portland) and you are looking for unique outdoor adventures, consider a couple of the best east side parks – including an extinct volcanic cinder cone and an interesting grotto. 

The Rocky Butte Natural Area on Portland’s east side 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 in Portland, OR. 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 revel in the Christmas Festival of Lights (during the month of December). 


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. Instead, you will be sipping cocktails or soaking in a saltwater pool (just be sure to make advance reservations for a swim!).

Headquartered in Portland, McMenamins is an Oregon brand that is known for renovating historic buildings and transforming them into truly spectacular venues of entertainment – and Kennedy School is one of the best. In addition to the multiple bars and pool, the property is also a hotel. (We talk more about places to stay in Portland below.) 

Visitors with a car might want to travel further afield to the McMenamins Edgefield property. Located in Troutdale (which marks 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 (oh, my!).

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More Things To Do in Portland, Oregon in 3 Days

Snow on Mt Hood, Portland, Oregon

We have highlighted the best things to do for your Portland Itinerary 3 Days trip – but we have a few more suggestions. 

In the event of wet weather, check out some of the museums in Portland. Or, if you want to see more of the region, embark on one of the day trips around Portland, Oregon.


Indoor Activities: Portland Museums

If foul weather keeps you from being outdoors during your weekend in Portland, don’t despair! There are plenty of cool places to see in Portland that are indoors. In fact, we already mentioned spending time at The Freakybutture Peculiarium and Museum – but there are many fascinating Portland museums.

We are featuring just a few of the top museums to include on your 3 Day Portland Itinerary. 



The Oregon Museum of Science and Industry is one of the best museums in Portland, OR. Featuring interactive and engaging science-based displays, the museum 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 see the 23 rooms in the mansion that are decorated in period pieces. Plus, the garden has a phenomenal viewpoint (which can be visited without paying entry into the mansion). 


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. 


OHSU Skyline Viewpoint and Gondola

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 viewpoint. 

For a group experience, join a guide for sunrise from the viewpoint – along with craft coffee and donuts. Get the details!


Portland Airplane Tour

What better way to see Portland sights than from above?! Visitors can take a short, scenic plane ride to view Portland from an incredible vantage point. Book it here!


Portland Day Trip Options

Columbia River Gorge Waterfall Trip Itinerary

During your weekend trip to Portland, taking a day trip is a perfect way to see more of the stunning surrounding region. Top day trips from Portland to add to a weekend in Portland are the Columbia River Gorge Waterfalls, wineries and the Oregon Coast. We are featuring a few of the highly-touted Portland tours. 


Morning Multnomah Falls and Columbia River Gorge Waterfall Tour

If you have a rental car, use our detailed Guide To The 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 that features the area’s beautiful waterfalls along the scenic byway. A guide offers interesting information about Oregon, while participants get to take in the breathtaking vistas. Book your spot!

Either way, the gorge is a perfect destination to include on a Portland weekend trip. 


Columbia River Gorge Adventure by Bicycle

When visiting Portland in a weekend, there is plenty of time to discover the outstanding beauty of the Columbia River Gorge on bicycle. The tour guide leads participants on an easy bike ride, making stops along the way to hike to nearby waterfalls. Guests can choose from morning or afternoon day trips from Portland. Find out more!


Willamette Valley Wine Tasting Tour

On your Portland trip, spend the afternoon visiting 3 incredible wineries in the picturesque Willamette Valley. The small-group tour features travel by minivan (and pick up/drop off at downtown hotels) and wine tastings at all 3 stops. Get more details!


Oregon Coast Tour From Portland

The Pacific Coastline in Oregon is a magnificent sight! We actually recommend taking a few days to complete a coastal drive – which you can read about in our complete guide to an Oregon Coastal Drive

However, visitors short on time can still get a glimpse of the coast on a full-day tour. This Portland day trip itinerary includes the incredible scenery from Cannon Beach, Ecola State Park and Oswald West State Park. Learn more here!


Vancouver, Washington

Just north of Portland 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 – which feels more like a small town and is often referred to as a suburb of PDX – 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 trip from Portland. 


Crater Lake National Park

Many visitors are tempted to squeeze in a road trip to Crater Lake into a weekend Portland itinerary – but, honestly, we think the 4-hour drive each way is too long during your short weekend trip. That said, if you are planning a longer trip to Oregon and need additional Portland vacation ideas, Crater Lake can be a fabulous option. We share many more tips for a longer vacation to Portland in the next section!


More Portland Itineraries

Portland Rose Garden Roses

Many people planning a trip to Portland wonder, “How many days in Portland, Oregon is enough?” While we think three days in Portland, Oregon is an ideal amount of time to see the sights, we could easily spend weeks exploring the city and region. However, what ultimately determines how long to plan a Portland vacation itinerary is interests, money and overall allotted time-frame.

Perhaps your time is limited to just a 2-Day Itinerary for Portland – or maybe you are planning a week-long Oregon vacation itinerary. To help in the planning process, we are sharing our top suggestions for alternative itineraries.


Portland Itinerary 1 Day

Whether you are taking a day trip to Portland or are planning to see Portland in one day as part of a larger PNW itinerary, there are numerous ways to spend your time. For us, a perfect Portland 1-Day Itinerary would include top sights, the best districts and iconic food.

To make the absolute most of a day in Portland, we recommend starting with a half-day tour by vehicle that takes in the top sights. Then, in the afternoon of your Portland 1 Day Itinerary, pick one district (or park) that is most appealing to you – and go discover it on foot. Depending on which neighborhood you choose, you could stop for a Voodoo Doughnut or Salt and Straw ice cream, then pop into a few craft breweries to get a good taste of what Portland has on offer!


2-Day Portland Itinerary

With 2 days in Portland there is just enough time to see the highlights. In order to create the best Portland 2-Day Itinerary, we recommend using parts of our above outlined 3 Day Portland Itinerary. However, for the best flowing Portland Itinerary 2 Days, on your first day, we recommend following our tips for Day 2. Then, on the second day, spend the morning at a park or on the Multnomah Falls tour; spend the afternoon in the Pearl District exploring the sights and sounds on foot.


Alternate Portland Itinerary 3 Days

While we think our outline for a 3-Day Itinerary in Portland, Oregon is the best way to see the city, it is certainly not the only way! Visitors who want to spend more time in nature can easily cut out some of the city sightseeing in favor of urban parks and the waterfalls tour.

And, vice versa, travelers most interested in city attractions can eliminate some of the outdoor adventures and spend more time in the districts and neighborhoods – like the Alberta Arts District or Mississippi/Williams.


4-Day Portland Itinerary

With 4 days in Portland, visitors have enough time to see the top attractions and go on a day trip from Portland. To create the best Portland Itinerary 4 Days, we recommend following our outlined plan for 3 days in Portland, then, on the last day, go on a full day tour.


Portland 5-Day Itinerary

Creating a 5 days itinerary in Portland, Oregon allows ample time for sightseeing, active adventures and a day trip. With 5 days in Portland, we recommend following the 4-Day Itinerary for Portland, Oregon (directly above), then spend the last day exploring another neighborhood or hop over the Columbia River and visit Vancouver, WA!


Oregon Itinerary One Week

As we already mentioned, we would have no problem planning a Portland travel itinerary for several weeks. That said, we think the best way to plan a Portland 7-Day Itinerary is to divide your time between the city and the coast.


7-Day Portland Trip Ideas: City and Coast

To create the best Portland and Oregon Coast Itinerary, you can use our day-by-day 3-Day Portland Itinerary – and then add on our Oregon Coastal Drive Itinerary. Our coastal drive trip plan features four days driving down the coast, visiting cute coastal towns (like Florence, OR) and hiking some amazing Oregon trails


7-Day Portland Trip + Bend and Crater Lake

Visitors who have already been to the Coast of Oregon could create a Portland to Crater Lake Itinerary. After 3 days in Portland, take a 4-day round-trip adventure to Crater Lake. If time permits, we recommend a visit to Bend, Oregon on the way back to Portland. 


Visit Portland or Seattle?

Many people debate whether to visit Seattle or Portland – and, we admit, it’s a tough call! Because of their proximity, we actually suggest visiting both by creating a Seattle and Portland Itinerary.

To make the most of a Seattle-Portland Itinerary, we think you should plan at least five days (but a week would certainly be better and might give you time to check out hip Spokane).

Top Tip: To plan a Seattle and Portland vacation, you can use the tips from our Seattle Itinerary!


Portland Oregon Map

Use this link to Google Maps to find your way to all the best things to do in Portland, Oregon.

Portland Itinerary Map by JetSettingFools.com


Travel Tips For Your Portland Itinerary

Now that you know what to do in Portland in a weekend, we have a few more tips for your trip.


Organizing Your Portland 3 Day Trip

We have shared detailed information about how to plan a trip to Portland, Oregon.

As you make your trip plans and reservations, we recommend using a travel planner to keep track of the details. Our Trip Planning Printables are perfect for making sure nothing falls through the cracks! 

Travel Planner Printables by JetSettingFools.com


Portland Food and Drink

Throughout our Best Weekend in Portland Itinerary we highlighted top restaurants and hip bars. The eateries that we shared are some of the most popular places to eat in Portland, OR – so we highly recommend making reservations in advance, if possible. 


When Is The Best Time to Visit Portland, Oregon?

We think the best time to visit Portland, Oregon is summertime to early autumn; specifically, from June until early October. Summers in Portland tend to be dry and sunny – which is perfect for outdoor activities (and the rose gardens).

The mild temperatures is what makes summer the best time to travel to Portland. However, the high humidity can be stifling and it’s also the height of wildfire season.

Late autumn through spring can be rainy, which could seriously put a damper on hikes and even neighborhood exploration. That said, with an umbrella, raincoat and some patience, it can be a fine time of year to visit Portland. In fact, for visitors from the Northeast or Midwest, the milder weather makes Portland a great US winter destination.


How To Get To Portland, Oregon

Portland can be reached by plane, train, bus or car. On our most recent Portland trip we flew from Columbus, OH and departed to Montana. When we need to buy plane tickets, we start our search for the best airfare on SkyScanner – but first be sure to read our detailed Tips for Booking Flights.

The Portland International Airport – PDX – 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.


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 the TriMet Bus and MAX Light Rail systems. Uber is also available as well as Lyft. It is easy to get around Portland on foot, scooter and by bicycle as well.

Additionally, visitors can get to the top Portland attractions on the Hop On Hop Off Pink Trolley Bus. In addition to making stops at all the best sights in Portland, the trolley also provides live on-board commentary and an open-air seating area for the best views. They offer 1- and 2- day passes. Get tickets here!


Where To Stay in Portland, Oregon

We think the best place to stay in Portland is central to all the best Portland, Oregon sights to see. That said, travelers with a car might prefer staying beyond downtown in one of the unique McMenamins hotels. 


The Paramount Hotel

We have stayed in various hotels on our trips to Portland – and can personally recommend staying at The Paramount Hotel. Located right in the heart of downtown, The Paramount Hotel offers clean rooms, comfy beds, an on-site restaurant, and sincere staff – all at an affordable price! Check rates and availability!


The Benson Hotel 

We have yet to stay at the historic Benson Hotel, but it is an iconic, luxury hotel in the Portland city center. Top features are the elegant rooms and top-notch service. Bonus amenities are the gym, laundry facilities and business center. Check rates for your stay!


McMenamins Kennedy School

We highlighted the McMenamins Kennedy Schoolhouse as one of the fun places to spend an evening imbibing and swimming, but it is also one of the best places to to stay in Portland! Located near the Alberta Arts District, travelers can use public transit and Uber to get to Downtown Portland sights and other districts. 

In addition to the multiple bars and heated swimming pool, the property also has an on-site movie theater. Each room is uniquely designed – some are even on old classrooms – and they all have ensuite bathrooms. The hotel does sell-out often, so book it in advance

Other fun McMenamins hotels in Portland are the McMenamins Crystal Hotel in Downtown PDX (check rates!) and the McMenamins Edgefield Portland Hotel outside of the city center (check availability!). 


Choosing where to stay in Portland for a weekend? Find the top hotels and great rates on Booking.com – and use our Top Tips for Booking Hotels to ensure you get the best value!


Portland Vacation Rental

Like many big cities, there are several holiday apartments that visitors can rent for their weekend stay. That said, for your 3 Day Portland Itinerary, we recommend staying in a hotel, rather than an Airbnb apartment.

We usually love staying in Airbnb accommodations –  they tend to be less expensive and feature a kitchen for preparing simple meals. However, for a short weekend trip to Portland, Airbnb fees can be excessive and with all the fabulous Portland food, you likely won’t be dining at your accommodations!


What To Pack For Your Portland Trip

We have a few final tips for your Portland vacation! Get our top Packing Hacks and more on our Ultimate Packing List. Need a Packing Checklist? Get your FREE Packing Checklist here!


Walking Shoes for Portland

We cover a lot of ground in our Portland 3-Day Itinerary! We recommend wearing a pair of comfortable walking shoes during your exploration. I like to wear these Columbia shoes for women and Kris likes Merrell trail shoes. Both of these shoes are good for most of the nearby Portland hikes, too!


Portland Weather Appropriate Clothing

While summer days in Portland can be hot, nights can be cool. We recommend packing clothing for your trip that can be layered – and even in the summertime, you will likely want at least a lightweight jacket. Extra layers are also essential if going on a jetboat 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, too!


Portland, Oregon Travel Guide

In our Portland weekend trip itinerary, we have outlined the best things to do in Portland, Oregon. However, it is always a good idea to have a travel guidebook – like this one – for even more information and to take notes!


Travel Camera for Oregon Photography 

Portland is an incredibly photogenic city! Rather than capturing the sights with your phone, we recommend upgrading to an actual travel camera. We use a Canon Rebel with an everyday 18-135mm lens. This camera comes bundled with all kinds of fun accessories, making it a perfect budget camera for budding photographers!



If you do plan on taking day trips from Portland into the nearby nature, we highly recommend bringing binoculars with you. 


Day Bag for your Portland Trip

Whether you travel with a backpack or a suitcase, for your long days of Portland sightseeing you will also want a great day pack to organize and secure all of your everyday travel items!


Oregon Travel Guides

Oregon ranks as one of our favorite places to visit in the United States – and we have heaps of tips for fellow traveler! Use our travel guides to help plan your perfect trip to Oregon. 


Start planning your US Trip! Search for the lowest airfares, the best accommodations and fun things to do…then start packing!  Want more travel planning tips? Head over to our Travel Planning Page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides Page!


We Want To Know: Is there anything you would add to our Portland Itinerary? What is your favorite way to spend a Weekend in Portland? Give us your best tips and advice in the comments below!


Visiting Other Top Destinations in The USA? 

We have been fortunate to travel to some of the Best Weekend Destinations in the country – and check out our top Underrated Places to Visit as well!

You can also take a peek at our detailed guides for Indy, Pittsburgh, Cincinnati, Denver, and Chicago. How about a weekend in New Orleans, Nashville, PhoenixBoston, Austin, or San Diego?


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Portland Itinerary A Weekend in Portland, Oregon by JetSettingFools.com