How long to spend in Portland (with suggested itineraries)!

Capture and bask in the quirky, hip, weird, and rich vibe of Portland. The city is home to the world’s biggest bookstore, vibrant craft beer scenes, and popular doughnut shops. Portland always has awesome things in store for every visitor – whether you plan to go on a weekend trip or stay longer and experience how locals live. Here’s how long to spend in Portland, Oregon with suggested itineraries from one day to a whole week…

The things you can do in Portland in a day

Perhaps you are on a business trip, layover, or road trip and landed in Portland territories. There are various places in the city you can explore in just a day.

  • Fuel up for some coffee in Downtown PortlandThe famous Stumptown Coffee Roasters in downtown Portland

The city is famous for its undying love for java. While strolling along the streets of Downtown, there are trendy coffee shops and craft roasters nearby. The Stumptown Coffee Roasters is a local favorite with locations spreading around Portland. There are about eighty coffee roasters in Portland, treating coffee as more than just a drink but a culture.

  • Powell’s City of Books

Powell's Books - largest bookstore in the world

It occupies almost a whole block and stands three stories high. The bookstore is so vast that you need to have a map to explore. You might also chance upon book readings as they host such events almost daily, with more than 500 author visits annually.

  • International Rose Test Garden

The International Rose Test Garden

Spend as much time as you want in the country’s oldest and continuously-operated public rose test garden. The garden is home to 10 000 roses and is also filled with roses named after the characters in the plays of William Shakespeare.

  • Pioneer Courthouse Square

Pioneer Courthouse Square Portland

This is a 40 000 square foot area hosting more than 300 events yearly. It is a vibrant urban park and one of the most visited places in the city. There is no need to rush when in the area.

  • Cap off the tour with a sumptuous meal in Nob Hill

Nob Hill Portland Oregon

It takes about a twenty-minute walk and various Victorian architecture where boutiques, cafes, and restaurants find a home. Paley’s Place Bistro & Bar serves Pacific Northwest cuisine. Do not forget to taste some craft beer while in the area.

The things you can do in Portland in two days

The weekend comes, and you decide to spend it in Portland. You can treat yourself to good food, well-crafted drinks, and excellent scenery for two days.

  • Voodoo Doughnuts

Voodoo Doughnut Portland

How about pairing a well-crafted coffee with sweets? The Voodoo Doughnut is a fan favorite in the city with locations near Powell’s main bookstore, and the other is in the city-suburban area across the river.

  • Portland’s food carts

5th Avenue Food Cart Pod

Head to the 3rd Avenue food cart area, which sits downtown. Most cuisines are from fresh, local ingredients.

  • Oregon Museum of Science and Industry

Oregon Museum of Science and Industry

This interactive museum houses eight labs and five halls full of hands-on exhibits devoted to chemistry, physics, paleontology, etc. The museum is for kids, families, and those curious about science.

  • Portland’s nightlife

Teardrop Cocktail Lounge

Your two-day stay won’t be complete without witnessing the city’s vibrant nightlife. As visitors say, this city in Oregon has a unique vibe that never fades, even on sundown.

  • Vintage shop and cafe hop on Division Street

Best vintage stores in Portland, Oregon

You will never run out of things to do on Division Street, as this is the city’s trendiest neighborhood where visitors can easily stroll for hours. It spans approximately fifty blocks of coffee houses and vintage-inspired boutiques.

  • Tour the breweries

Barley Head Brewery

It is a must to taste Portland’s beer when in the city. Going on a brewery tour will provide insights about Portland while taking you to the excellent breweries.

  • Crystal Springs Rhododendron Garden

Crystal Springs Rhododendron Garden

Portland is also home to several parks and natural attractions. Escape the metro’s hustle and bustle, visit this gem, and explore the network of trails through rhododendron ponds and groves.

Where to stay?

Pearl District Portland

For visitors, some famous neighborhoods include Hawthorne, Downtown, Nob Hill, and the Pearl District. Accommodations like the Crystal Hotel, which sits in the city’s heart, are close to several attractions like Powell’s City of Books.

The things you can do in Portland in three days

Portland sure is a city that needs to be explored for days. The town’s abundance of natural parks, creative scenes, delectable beverages, and cuisine is worth the extended stay. You can visit the locations mentioned above and attractions and add the below to your list.

  • Pittock Mansion

Pittock Mansion Roses

Besides all the famous and hip destinations this city offers, you can also learn and appreciate Portland’s culture and history by visiting this mansion. It even provides an excellent viewpoint of the city.

  • Portland Art Museum

Portland Art Museum - Portland

It’s worth visiting as this art museum is the oldest in the Pacific Northwest. It houses most of Oregon’s prestigious collections, such as the pieces from the European masters, contemporary American works, and Japanese screen prints.

  • Saturday market

Portland Saturday Market - Portland

Since its launch in 1974, the Portland Saturday Market has featured hundreds of booths showcasing local arts and crafts, clothing, pet, and toy supplies manufactured from every imaginable material.

  • Tom McCall Waterfront Park

Tom McCall Waterfront Park Spring

The park hosts several activities here and offers one of the best views of the Portland skyline. Even when the city is not celebrating anything, the park still serves as an excellent place for afternoon strolls and picnics.

  • Forest Park

Skyline Boulevard in Forest Park - Portland

The city boasts several parks for outdoor enthusiasts. Portland may be famous for having more rain, but that does not prevent visitors from exploring nature. There are varieties of hikes for all levels and activities for visitors curious about birds.

Where to stay?

Society Hotel Portland Oregon

Most touristy destinations sit in west Portland Northwest and Pearl Districts. The Society Hotel exudes a rustic hipster of vintage aesthetics and exposed bricks. Meanwhile, the Park Lane Suites & Inn is in the residential northwest neighborhood, still walking distance from the vibrant Pearl District.

The things you can do in Portland in five days

While you can mix and match all the mentioned attractions in this article, this itinerary below will guide you in exploring the city for five days.

Day 1: You can spend the first day exploring downtown Portland. With compact blocks, an exciting mix of architectural types, buildings, and parks, this neighborhood is ideal for walking or biking and visiting the following:

Portland Japanese Garden

  • Pioneer Courthouse Square
  • Portland Art Museum
  • Tom McCall Waterfront Park
  • Japanese Garden
  • International Rose Test Garden
  • Powell’s City of Books
  • Pittock Mansion

Day2: The Oregon Coast is an ideal destination for relaxation and avoiding the city’s hustle and bustle.

Cannon Beach, Oregon, Summer

  • Cannon beach
  • Devil’s Cauldron or Devil’s Punchbowl
  • Tillamook Creamery
  • Rogue Brewing

Day 3: Northeast Portland has distinct neighborhoods; each has a unique flair, food style, and shopping scene.

Alberta Street Portland Oregon

  • You can explore the Alberta neighborhood, which shows a quirky artist vibe with several delicious restaurants and cute shops. The shops here sell arts and crafts supplies, gifts, handmade dresses, and a funky vintage selection.
  • Boise District in Northeast Portland also has shops for local art prints and cards, camping gear, backpacks, and western clothing styles.

Day 4: You can use your car or rent for the fourth day and head to Columbia Gorge to see the state’s lovely scenery. Spend some time at the Multnomah Falls and have a meal at the Multnomah Falls Lodge.

Day 5: Explore the breweries and vineyards in the city. Besides craft beers, Portland is also famous for its pinot noirs.

Where to stay?

Alberta Arts Gem Brimming with Color and Light - Airbnb1

  • Pearl District
  • Woodlawn
  • Mississippi Avenue
  • Alberta Street

The things you can do in Portland in a week

Tom McCall Waterfront Park - Portland

Day 1: Explore the West of Portland by starting from the waterfront loop. Stroll along with the beautiful view of the city and stop by at the Saturday market (if your visit falls on a Saturday).

There are various activities and attractions to check out in the Pearl District. Warm up on your trip by exploring the vibrant and creative scene of the city.

Day 2

Boutique shopping in the Pearl District

  • Rent a bike and head to the East of Portland.
  • Shop from boutiques, resale, and vintage stores between 32nd and 50th Hawthorne Blvd.
  • Climb or walk up Mt. Tabor and explore dog parks, reservoirs, and hiking trails and watch the sunset.

Day 3

Wine tasting tour Willamette Valley

  • Go on a wine tasting tour in the Willamette Valley
  • Explore the art galleries, breweries, and restaurants at the Cannon beach

Day 4

Arlene Schnitzer Concert Hall - Portland

  • Hike the trails at the Harts Cove or Drift Creek Falls
  • Spend some time on the Oregon coast before heading back to the city
  • Watch a movie at the city’s historic theaters like the Academy, Laurelhurst, Arlene Schnitzer Concert Hall and Hollywood. 

Day 5: Get to know the city more by exploring notable neighborhoods, including:

Multnomah Village Portland

  • Mississippi Avenue is home to bars, restaurants, and an enormous center for recycled building materials.
  • Multnomah Village is a charming little neighborhood with toy stores, cafes, and tea shops. Experience the old-school Portland in this area.

Day 6: Explore the outdoors

Columbia River Gorge Oregon

  • Columbia River Gorge
  • Forest Park
  • Mount Hood
  • Trillium Lake and White River

Day 7:

Voodoo Doughnut Portland

  • Voodoo Doughnuts or Blue Star
  • Pittock Mansion
  • International Rose Test Garden
  • Powell’s City of Books
  • Portland Art Museum

Where to stay?

Central Eastside Portland Oregon

  • The city’s Central Eastside is close to the river and ideal for walking to downtown Portland and other attractions.
  • For first-timers, you stay in the Pearl District or Downtown Portland.


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