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The Ideal 3 Days in Portland Itinerary (Oregon)

The Ideal 3 Days in Portland Itinerary (Oregon)

Planning your 3 Days in Portland Itinerary? You’re in the right place! Here you’ll find the perfect guide to discover Portland’s gems and delicious treats, and to make the most of your time in the city.

This is a guest post by Valentina of Valentina’s Destinations.

If you are road tripping through Oregon, be sure to spend at least 3 days in Portland, a truly fabulous city. Oregon is a state in the Pacific Northwest known for its lush forests, plethora of waterfalls, and overall immense natural beauty.

Portland is Oregon’s quirky capital city that’s home to some of America’s best food trucks, doughnuts, and craft beer.

There’s more than just food to enjoy in Portland. It’s one of the best places in the country to go thrifting. You’ll be sure to discover some amazing vintage pieces! There’s also scenic hiking, world-class museums, and an International Rose Test Garden. Tourists will find no shortage of activities to enjoy in Portland rain or shine, so if you were still wondering whether to spend 3 days in Portland or any other city in Oregon, your answer is right here!

The best time to visit Portland is June through August. Around this time, the weather is consistently warm and you’ll be able to enjoy roses in full bloom. Room rates and traffic dies down by September. May is also a safe bet for travelers seeking to avoid the crowds. Avoid visiting in December or February, frequent rains and chilly temperatures aren’t so pleasant. 

▶ For short-term travelers, it is recommended to stay in downtown Portland. Find more information about Portland Hotels.

Now, let’s tackle this Portland Itinerary for 3 days, perfect for a fantastic Portland weekend trip. Start packing, what are you waiting for?!

Day 1 | Portland Itinerary

On your first day in Portland you’ll take a walking tour of downtown, that with its artsy and hipster character reminds me of some parts of Downtown LA.

You’ll also explore Powell’s City of Books, shop for vintage clothes, and experience Pacific Northwest style sour beers. Since enjoying all of Portland in 3 days is not quite possible, we’ll begin with the important aspects of the city: pastries!

Ken’s Artisan Bakery

Start your day with a fresh danish from Ken’s Artisan Bakery. If you’ve ever considered baking your own bread, you might have come across Ken’s book “Flour Water Salt Yeast.” This book has won a James Beard award and an IACP (International Association of Culinary Professionals) award. 

If you haven’t read the book, you might be convinced to purchase it after your visit. If you have tried your hand at making some of Ken’s recipes, you’ll find a visit to his flagship bakery all the sweeter.

At Ken’s Bakery, you’ll find a healthy assortment of bread, croissants, cookies, sandwiches, and soups. You can also grab a coffee brewed with Proud Mary coffee beans. Classic favorites include the Goat Cheese and Leek croissant, and Ken’s Hero sandwich. There’s no better way to start your day!

Secrets of Portlandia Tour

Secrets of Portlandia is Portland’s most popular walking tour. It’s a free walking tour that runs on tips, so be sure to tip your guide. The Secrets of Portlandia tour takes place every day at 11 AM. You’ll meet in front of the Pioneer Courthouse.

Along the tour, you’ll learn more about Portland’s history and culture through entertaining and comedic stories. It’s an engaging experience that you won’t forget. Highlights include Old Town, Chinatown, and the Pearl neighborhoods. You’ll also hear ghost stories and learn the story of VooDoo Doughnuts. 

This tour is a perfect way to kick off a visit to Portland. Your guide can assist with insider tips and restaurant recommendations. 

➤ If you’d like to experience the city from a slightly different perspective, check out this Downtown Portland Bike Tour. You’ll ride through Portland’s historic west side, explore art galleries, food carts, and breweries, and head to Waterfront Park for amazing river views. Your guide will fill you in with all the details about Portland’s history and culture. ➥ BOOK IT HERE

➤ As an alternative for your first glimpse of the city on this 3-day itinerary in Portland, choose the Portland Afternoon City Tour. It’ll take you to see the city’s top sights and attractions, to visit the only ”vertical street” in North America and see more than 500 varieties of roses at the International Rose Test Garden. Views of waterfalls, docks and cobblestone streets are also guaranteed in this Portland itinerary tour. Round-trip transportation from your hotel is included. ➥ BOOK IT HERE

Powell’s City of Books

Powell’s City of Books is the largest independent new and used bookstore in America. It’s located in Portland’s Pearl District in downtown Portland. It’s been featured by several blogs and magazines over the years. 

If you have room in your suitcase, consider a book from Powell’s as a memorable souvenir. You can find anything from rare collectables to budget-friendly classics. There are so many books at Powell’s that they occupy a city block. In fact, there is over an acre of retail space and over 3,000 sections. If you’re a bookworm, you’re in danger of spending here the whole of your first two days in Portland, Oregon. Even so, don’t miss this iconic place!

While you are in the neighborhood, take this opportunity to snap a photo near the Keep Portland Weird Mural and the Portland Oregon White Stag Sign. You can visit these instagrammable hot spots in under 15 minutes from Powell’s City of Books. 

Vintage shopping

When in Portland, shop! Portland is world-renowned for its collection of vintage shops. There are about 50 vintage shops in Portland, and many more antique boutiques. Clothes aren’t made like they used to be! High-quality pieces from bygone eras never go out of style!

Don’t miss your opportunity to go vintage shopping in Portland. You won’t regret it!

You can find a handful of cool vintage shops in Hawthorne district. Magpie, House of Vintage, Red Light Clothing Exchange, and In Real Life are all located along a short stretch of Hawthorne Boulevard.
Magpie is a great place to find 90s tees as well as children’s apparel. House of Vintage is a sprawling store with sections for different dealers. 60 dealers offer unique clothing pieces, jewelry, and accessories. There are also some furniture, pop culture items, and collectables; a real treat for shopaholics, and probably their favorite part of this 3 day Portland itinerary! 

Cascade Brewing Barrel House

Portland isn’t just the ‘City of Roses,’ it’s also ‘Beervana.’ This nickname is well-deserved as there are just about 70 breweries within city limits. That’s more breweries in one city than there are anywhere else!

With so many breweries to choose from, you’ll need a little help deciding where to start.

End the first evening of your Portland travel itinerary with a classic city’s favorite, a pint of barrel-aged Northwest Sour Ale. Cascade Barrel Brewing opened their doors over 20 years ago. Although, it wasn’t until 2006 that they started making and perfecting sour beers. Cascade Brewing was instrumental in pioneering the classic Northwest-style beer movement. 

Day 2 | Portland Itinerary

On Day 2 in Portland, you’ll discover why they call it the ‘City of Roses,’ and catch some spectacular views. 

HunnyMilk for brunch

Start day 2 in Portland with a delicious breakfast at HunnyMilk. HunnyMilk is first come first served, so they don’t take reservations. Although, you’ll have an easy enough time finding a table before 10 AM. 

HunnyMilk specializes in brunch. They offer hearty selections of creative concoctions. They also serve craft cocktails and coffee, quite necessary to start the second day of your itinerary for Portland, Oregon. Once you’re satisfied and awake, let’s get moving!

International Rose Test Garden

No visit to Portland is complete without checking out the International Rose Test Garden. You’ve probably heard Portland being referred to as ‘the city of roses.’ The first rose bush came to America’s Pacific Northwest in 1837. 

Although, it wasn’t until the 1890s when Georgina Pittock sensationalized them and created the Portland Rose Society. Consider visiting the Pittock Mansion, it’s not too far from the International Rose Test Garden. 

In the 1900s, roses were planted in great numbers for the Lewis and Clark Exposition being held in Portland. Although, the most famous historic event that led to Portland’s claim to fame in Roses was WWI. At the time, European hybridists began sending their roses to Portland to protect them from the bombings, and the international rose test garden was born! Now, it holds the title of being the oldest continuously running public rose garden in America. 

Portland Japanese Garden

While visiting the International Rose Test Garden, it’s easy enough to stop by the Portland Japanese Garden. This 12-acre urban oasis contains 8 different landscape areas. You’ll discover babbling brooks and quaint walkways.

Since the garden overlooks the city, you can see all the way to Mt. Hood on a clear day. This is considered one of the most authentic Japanese gardens in America, together with the Japanese Tea Garden in San Francisco. It was visited by the former Ambassador to Japan Nobuo Matsunaga. 

Lunch at Higgins 

Stop at Higgins for lunch. This is an excellent place to try Pacific Northwest-style cuisine. Higgins is located downtown. It’s a casual spot that is proud to serve farm-to-table, in-season, favorites. 

Hike in Council Crest Park

Head over to Council Crest Park. It’s the highest point of elevation in the city. As you might expect, it offers phenomenal views. From here, you can gaze over the surrounding cityscape and even spot some of the surrounding mountain peaks.

If you don’t feel like hiking – there’s no need. Just drive up all the way up to the scenic vista. It’s an excellent spot for a picnic. Alternatively, you can hike to Council Crest. The Marquam Trail is one access point. From Marquam Park, you’ll hike just over 3 miles out and back while gaining nearly 800 feet in elevation.

This is a moderate hike that takes most trekkers about 2 hours to complete. It’s heavily trafficked, so you can expect to run into others along the trail. 

Dinner at Departure Restaurant 

Departure Restaurant is one of Portland’s rooftop bars. It’s a hip place with characteristically urban views. After a day out in nature, you’ll enjoy dining here as a reminder that you’re in a big city.

Departure won a Traveler’s Choice award in 2020. Their menu features pan-Asian cuisine in an elegant setting. Be sure to make your reservation an hour before sunset for the ultimate romantic experience. 

Day 3 | Portland Itinerary

Now that you’ve been 2 days in Portland, you probably get what all the fuss is about! On your third day in the city, you’ll try one of the famous VooDoo doughnuts and take a day trip outside the city. You can get to the Willamette Valley or Columbia River Gorge area in under an hour from Portland.

If you’re spending the weekend in Portland, one of these should definitely make it into your itinerary.

Voodoo Doughnuts 

Start the last of your 3 perfect days in Portland with an epic Voodoo Doughnut

VooDoo Doughnuts is Portland’s claim to doughnut fame. VooDoo’s flagship location in downtown Portland is right by the ‘Keep Portland Weird’ Mural and the Portland Oregon sign. 

VooDoo is famous for its unconventional flavors. Try ‘Espresso Yo’self,’ ‘the Homer,’ and ‘Viscous Hibiscus.’ Since there are several locations across the city, there’s no excuse to miss this! 

On your third day, this Portland Itinerary gets you outside of the city! Two of the best day trips from Portland include Willamette Valley and the Columbia River Gorge. Although, if you have more than 3 days, you should consider visiting Bend. Bend, Oregon is an excellent springboard destination for travelers hoping to visit Crater Lake National Park or the Painted Hills. 

Option 1: Willamette Valley Winery Day Trip

The first option for a day trip from Portland in this 3-day itinerary is Oregon’s Willamette Valley. Wine enthusiasts will delight. While Oregon has 19 distinct viticultural areas, the Willamette Valley is the largest and most visited. It’s an easy day trip since you can drive there in under 1 hour. Oregon wine month is May, so you’ll have access to additional wine events if you are lucky enough to visit around this time. 

Oregon’s first vines were laid down by pilgrims following the Oregon Trail in the 1840s. Today, over 700 independent wineries dot the state of Oregon. Among them, over 70 varietals are grown. Due to Oregon’s cool climate, it’s the Pinot Noir grape that is exceedingly popular. 

Visit Domaine Serene Winery in Oregon’s Willamette Valley. Its sprawling and elegant estate is worth seeing for yourself. Visit for a wine tasting and light fare. Next, head over to Penner-Ash for another unforgettable experience.

Penner-Ash Wine Cellars has an equally impressive estate with gorgeous panoramic views of rolling hills. Reserve your spot on their winery tour and tasting for the ultimate experience. It’s a great way to learn about the unique Oregon soils and gravity flow winery. 

➤ This Willamette Valley Wine Tour takes you on a 7.5-hour trip to visit 3 to 5 vineyards in the valley, allowing you to sample as many wine varieties as you wish without having to worry about driving, and you’ll enjoy a picnic style lunch at one of the wineries. ➥ BOOK IT HERE

Option 2: Columbia River Gorge Day Trip

If you’ve got access to a vehicle, the Columbia River Gorge is worth including in your Portland, Oregon itinerary. This pristine recreation area was formed by moving glaciers, excess snowmelt, and the unrelenting rain which the Pacific Northwest is so famous for.

It’s only 30-45 minutes driving outside of Portland. Yet, there are almost endless opportunities for adventure. When in Oregon, it’s customary to visit a waterfall. There are hundreds of waterfalls in Oregon and more than 90 in just the Columbia River Gorge area. 

While visiting the Columbia River Gorge, be sure to check out Multnomah Falls. It’s one of the most visited tourist attractions in the state of Oregon. This is Oregon’s tallest waterfall at over 600ft. Climb the steep hiking trail to the popularly photographed bridge mid-way. Panoramic views galore! For travelers looking for a quieter trail, consider hiking to Wahkeena Falls and Fairy Falls

When driving through the Columbia River Gorge area, you must stop at the Crown Point Vista House. At this century-old observatory, you’ll discover some of the most mesmerizing 360° views. 

➤ If you’d rather not drive or didn’t rent a car during your Portland 3-day itinerary, you can still visit the area with the Columbia River Gorge Waterfalls Tour. This half-day tour is limited to 12 people, so you’ll enjoy a personalized experience. You’ll get to explore the Multnomah Falls and Historic Lodge, discover several waterfalls in the area and visit the Bonneville Fish Hatchery, the largest in Oregon! ➥ BOOK IT HERE

➤ If chasing waterfalls is not your thing, you can still enjoy the beauty of the area in this 2-Hour Columbia River Gorge Sightseeing Cruise. The boat takes you under the Bridge of the Gods, and you’ll also pass the Bonneville Dam, Native American fishing platforms and locations where kite and wind surfers practice their skills, gainins spectacular sights as you glide along. A full-service bar is available on board, to make your trip even more enjoyable. ➥ BOOK IT HERE

 ➤ Alternatively, if what you’re looking for is more adventure, the Columbia River Gorge Tour should be your choice. You’ll explore the wonderful area and nature trails riding a bike, and you’ll stop for hikes at some breathtaking waterfalls. The tour is suitable for all skill and fitness levels, and includes snacks and round-trip transportation. ➥ BOOK IT HERE

3 Days in Portland, Oregon – Frequently Asked Questions

How many days should you spend in Portland Oregon?

3 days are enough to enjoy the best of Portland and its main attractions. You can even squeeze in a day trip to the Willamette Valley or Columbia River Gorge during that time! If you’d like to visit the Oregon Coast or explore some of the National Forests nearby, however, you should add a couple more days to your itinerary.

Is Portland worth visiting?

Yes! Portland is a beautiful city surrounded by nature and offering many diversions; from hikes and waterfalls nearby to wineries, delicious pastries and breweries, vintage shops to die for and great culture. But enough with the spoiling, start packing for Portland!

Author Bio: Valentina has always been obsessed with researching, organizing, and planning her vacations. She knows that many people don’t have the time and energy to do this, but they still want to get the most out of their travels.

Valentina’s Destinations allows her to help other busy professionals maximize their experiences. Valentina is originally from Serbia, but she grew up in Chicago. She loves hunting down local restaurants, unique experiences, and hidden gems. Follow her adventures on Instagram & Facebook!


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