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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 experience the best of the city. Our Portland Itinerary features the top city highlights – and visitors to Oregon can use our outline to create their Best Weekend in Portland trip plan.
Portland in a Weekend
Spending a weekend in Portland, Oregon is an excellent way to get acquainted with the city that so proudly proclaims to be weird. With an easy-going atmosphere and cool 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. Since my cousin had moved, on my subsequent visits, 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 the best 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 best help fellow travelers, we offer suggestions for alternate Portland trip itineraries at the end of the post. 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.
Weekend in Portland Itinerary
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.
This Portland blog contains everything you need to plan your trip! Save, Bookmark or Pin our Portland, Oregon travel itinerary so that you can access it while planning your trip to Portland!
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 cities most vibrant districts, Pearl.
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.
Start your exploration of the district at the landmark Powell’s City of Books, which is the largest independent bookstore in the world (for new and used books). The massive bookshop covers an entire city block and ranks on many lists as one of the Top 10 Bookstores in America.
After perusing the selection of books, take a walk through the North Park Blocks, a green city oasis since 1869.
Detour Into Old Town Chinatown Portland
Detour from Pearl District into the Old Town Chinatown District. Although not as impressive as other American Chinatown districts – like the one in San Francisco – there is an ornamental gate (at NW 4th Ave and W Burnside St). However, 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).
Make your way back into Pearl District and walk through Jamison Square, which features fountains where you can cool your feet in the summertime.
Evening Entertainment: Dinner, Drinks and Live Music in Portland OR
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 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 brewed 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 brewery tour in the district, making stops at 10 Barrel Brewing, Rogue Pearl Public House, Back Pedal Brewing and Von Ebert Brewing. For handcrafted cocktails, try Teardrop Lounge and Vault Cocktail Lounge.
Looking for a fun activity for your girls’ or guys’ weekend in Portland? Discover the best craft beer in the city on a mid-day craft beer tour!
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. They even have an in-house brewery!
Day 2 Of Your Weekend in Portland Itinerary
On the second day of your Three Days in Portland, start with some classic Portland food experiences, then see Downtown Portland sights, and end the day across the Willamette River in the Buckman District.
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!
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 now, as well). Their gourmet donuts include flavors like Blueberry Basil Cake and Mexican Hot Chocolate.
Pro Tip: If you really want to go crazy, try donuts from both 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, the Portland Saturday Market is a must-see on your weekend getaway to Portland, Oregon. Opened in 1974, the free outdoor market features more than 350 local vendors – plus there is always live music and heaps of international food truck options (and it’s open Sunday as well!).
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 the city – 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 more interested in learning about the food culture in the city 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 restaurants and food carts in the city – and the guide shares the city history throughout the tour. This tour is limited to just 12 people, so reserve your spot in advance!
Buckman District Portland
In the evening of your second day in the city, 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) 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.
An Evening Out on Day 2 of Your Portland Weekend Trip
The city’s vibrant districts are a fun place to delve into a night of food, drinks and entertainment.
Spend an Evening in Buckman
If you want to stay in Buckman for dinner, head to Hawthorne Street – which is filled with character and lined with vintage stores. The district hosts numerous restaurants – from fine dining to farm fresh to funky fare.
That said, our favored 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 to best enjoy the experience.
After dinner, sample more Portland craft beer as you bar hop from brewery to tap room in Buckman. Use this link to Google Maps for the locations of 6 recommended Buckman brewery tap rooms.
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 Ikes Fish Sauce Wings at Pok Pok – 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.
A Night on North Mississippi Avenue
Shops, restaurants, bars and theaters line the festive five-block stretch of North Mississippi Avenue in a historic North Portland neighborhood. An area of recent renewal, the lively district is on point for a fun night out!
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.
Sports enthusiasts can catch a game when visiting Portland. The NBA Portland Trail Blazers play an in area just across the river from downtown. The city also hosts an MLS soccer team, the Portland Timbers – and numerous other teams (like the collegiate baseball Portland Pickles and the junior ice hockey Portland Winterhawks).
Day 3 of Your Portland Weekend Itinerary
On Day 3 of your weekend in Portland, Oregon you will need to decide between a few of the best city attractions. Either spend time in the beautiful outdoors – or, in the event of foul 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.
Pine State Biscuits for Breakfast
Start the final day of your weekend in Portland at a city hot spot: Pine State Biscuits. The modern diner excels at hearty, home cooked meals that are lip-smacking 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 city’s nature is astounding! 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 city 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. Memorials, statues, museums and playgrounds are more park highlights – and a reason to stick around the area even longer.
West of Washington Park, visitors can hit the trails in the even larger Forest Park. The hillside urban park overlooks the Willamette River and features 70 miles of trails. Interested trekkers can detour from the park to walk across the historic St. Johns Bridge.
If you want to spend the entire day in the area, wander through the quaint Northwest District and eat lunch at a hip local restaurant – or dine at the charming Nob Hill Food Carts. Afterwards, cool down with some ice cream from Salt and Straw, an artisan Portland-based ice creamery featuring unique flavor combinations.
Willamette River Boat Rides
Alternatively, get outdoors and 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 three tours to choose from – Willamette Falls, the Shipyards or a quick scenic sprint along the waterfront and under bridges. The rides – which are good, thrilling fun – guarantee that passengers will get wet!
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 your Portland vacation is not your first trip to the city and you are looking for more unique outdoor adventures, consider heading to the east side of Portland.
Extinct Volcanic Cinder Cones
On Portland’s east side, there are two excellent neighborhood parks – both of which are extinct volcanos – that you can include in your Portland Itinerary.
- Mount Tabor: Numerous paths weave through forests, around reservoirs and up Mt Tabor.
- Rocky Butte Natural Area : A gorgeous lookout point, the elevated Rocky Butte Park offering stellar views of Mount Hood.
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.
Indoor Activities: Portland Museums
If foul weather keeps you from being outdoors during your weekend in Portland, then consider visiting one of the many fascinating Portland museums.
Top city museums to include on your 3 day Portland itinerary are:
- OMSI (Oregon Museum of Science and Industry)
- Pittock Mansion (which is located just north of Washington Park and has a phenomenal viewpoint!)
- Oregon Historical Museum
- Portland Art Museum
- The Freakybutture Peculiarium and Museum
Portland Day Trip Options
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 waterfalls, wineries, the Columbia River Gorge and the Oregon Coast. We are featuring a few of the most highly-touted Portland tours.
Morning Multnomah Falls and Columbia River Gorge Waterfall Tour
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 the 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 detailed blog post: Oregon Coastal Drive!
However, visitors short on time can still get a glimpse of the coast on a full-day tour. The Portland day trip itinerary includes the incredible scenery from Cannon Beach, Ecola State Park and Oswald West State Park. Learn more here!
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 one-way 4-hour drive is just a bit too long during your short weekend trip. That said, if you are planning a longer trip and need additional Portland vacation ideas, Crater Lake can be a fabulous option. We share more tips for a longer vacation to Portland in the next section.
More Portland Itineraries
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 city 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 regional itinerary, there are numerous ways to spend your time in the city. 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 city 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 the city has on offer!
2-Day Portland Itinerary
With 2 days in Portland there is just enough time to see the city 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 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 city districts – 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 city 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 from the city.
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 – like Mississippi, going to Forest Park or hop on the other side of 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 spend time in the city and time on the coast.
7-Day Portland Trip Ideas: City and Coast
To create the best Portland and Oregon Coast Itinerary, you can simply use our day-by-day 3-Day Portland Itinerary – and then use 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. Our route then loops looping back up to Portland.
7-Day Portland Trip and Crater Lake
Visitors who have already been to the coast could instead create a similar Portland to Crater Lake Itinerary. Spend 3 days in Portland (as outlined) then take a 4-day round-trip adventure to Crater Lake. If time permits we completely 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! We think both cities are fabulous! Because of their proximity and ease of getting between the two cities, instead of picking one over the other, we 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 to see the two cities (but a week would be better and might even 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.
More 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.
When Is The Best Time To Visit Portland, Oregon?
We think the best time to visit Portland, Oregon is in the summertime into 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, be aware that humidity can be high during the height of the 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 many visitors, the usually mild winters make it a great winter destination – plus, it’s perfect for celebrating the holiday season.
How To Get To Portland, Oregon
Portland can be reached by plane, train, bus or car. We prefer flying – we are JetSetting Fools, after all! On our most recent Portland trip we arrived from Columbus, OH and departed to Montana. When we need to buy plane tickets, we start our search for the best airfare on SkyScanner – you can find our detailed tips for Booking Flights here.
The Portland International Airport – PDX – is the main city airport. The airport is well-connected to the city via public transport, but private ground transportation from the airport is also available and can be booked online.
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.
Where To Stay in Portland, Oregon
We think the best place to stay in Portland is in the heart of the city near the best Portland, Oregon sights to see.
For your 3 Day Portland Itinerary, we recommend staying in a hotel, rather than an Airbnb apartment. We usually love staying in Airbnb accommodations – because they tend to be less expensive, plus they have a kitchen for basic 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.
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!
Pro Tip: We have yet to stay at the historic Benson Hotel, but it is an iconic, luxury hotel in the Portland city center.
What To Pack For Your Portland Trip
Walking Shoes for Portland
We cover a lot of ground in our Portland 3-Day Itinerary! We recommend wearing a pair of comfortable city walking shoes during your neighborhood 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 mountains. Remember to bring a wide brimmed hat, good sunscreen and insect repellent, 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 more information.
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 camera. We use a Canon Rebel with an everyday 18-135mm lens. The camera comes bundled with all kinds of fun accessories, making it a perfect budget camera for a budding photographer.
Not necessary in the city, but 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
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!
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