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A Perfect Weekend in Portland, Oregon (2-Day Itinerary)

If you’re looking to visit one of America’s most up-and-coming once hidden gems, Portland is the place to go! It’s filled with unique neighbourhoods, trendy shops, delicious cuisine, and much more. There’s truly something for everyone during a weekend in Portland, Oregon if you’re into culture, a quirky vibe, and a good time.

weekend in portland oregon

Are you looking to have the perfect weekend in Portland? With no shortage of special experiences to be had in Portland, this two-day itinerary will break it down for you. We’ll also share how to get around, where to stay, and our favourite spots to check out.

If you’re excited to try new foods, Portland will definitely impress you! From visiting a famous bookstore to exploring incredible culture, get ready for an unforgettable weekend in Portland, Oregon.

Read more: A Culture Lover’s Guide to New York, Los Angeles, and Seattle

How to Travel Around Portland 

Getting around Portland is known to be convenient. Because of its walkability and public transportation, you can easily spend a weekend in Portland without a car.

Light Rail System

The Max Light Rail System is efficient for travellers to get around the city. There are more than 90 stations and 60 miles of tracks that connect downtown Portland to the metro area. It provides easy transport to and from the airport, too.

The train runs about every 15 minutes throughout the day, every day. It is a little less frequent in the early mornings and late evenings. You can purchase a day pass for $5, less for honoured citizens and children. You can find ticketing machines at the rail stations or use your phone for the Hop Fastpass system.

portland bridges

Portland Streetcar

The Portland Streetcar takes passengers around downtown, the Pearl District, and other popular areas. The streetcar provides modern, frequent, and affordable transportation. It operates 3 lines and about 16-miles of Portland’s Central City.

The Portland Streetcar works similarly to the rail system. It runs about every 15 minutes and you can access it from early morning until late evening. You can pay per ride onboard any streetcar or use the Hop FastPass system.

On Foot

Portland is considered the 13th most walkable large city in the US. Most people say that they feel safe walking around the city, especially since there are police foot patrols in high-foot-traffic areas. 

Many areas are easy to explore on foot including the Pearl District, Old Town Chinatown, and Downtown. In fact, you’ll find in this guide that there are many attractions close to one another and are easier to visit by walking from one place to another.

portland cherry blossom

Day One in Portland

Now that you know how to get around, let’s take a look at how to spend the first day of your weekend in Portland. Explore the city’s culture, do a little book shopping, and enjoy some delicious food.

Visit Powell’s Bookshop

Check out new, used, and rare books at the famous Powell’s Bookshop. Their main location is located in the Pearl District and has over one million books. It also features a cafe and bookstore. You can find another location on the other side of the river which also has a cafe.

Get Coffee and Doughnuts

What better way to spend a weekend in Portland than by indulging in tasty coffee and treats? In fact, doughnuts are a Portland staple to the extent that they even have an underground doughnut tour.


Blue Star Donuts is a household name in Portland. Before the pandemic, there were several locations throughout the city. However, it’s now down to a couple of locations including one right below downtown Portland just a mile from Powell’s main bookstore.

Enjoy a creative, gourmet doughnut with a cup of noteworthy coffee at Bluestar. Their menu includes a chocolate almond ganache, blueberry bourbon basil, and so many more unique options.

Voodoo Doughnuts

Another fan favourite for Portland locals and tourists alike is Voodoo Doughnuts. There are two locations — one in the old town and also close to Powell’s main bookshop while the other is across the river, in the town’s larger and more suburban area.

voodoo doughnuts portland oregon

They make fresh, creative doughnuts daily. Their signature voodoo doll doughnut and coffee are iconic and they offer tons of other delicious menu options, too. 

Get Creepy at The Freakybuttrue Peculiarium and Museum

Any proper weekend in Portland entails a weird but absolutely fascinating trip to the Freakybuttrue Peculiarium and Museum. This unmatched museum boasts unique exhibits and countless photo ops. You can purchase art from the gallery and cool souvenirs from the gift shop. If you’re craving a sweet treat, they’ve even got an ice cream parlour.

Indulge at Portland’s Food Carts

If you look forward to eating your way through a new city, Portland is the place for you! Portland’s food cart scene is unlike any other. Instead of moving around, Portland’s food carts settle in groups making it easy to sample a few at a time.

Local chefs use fresh, local ingredients to craft mouthwatering cuisine. The 3rd Avenue food cart pod located downtown is a great one featuring diverse eats! Here are just a few tasty options:

  • LoveVerona Pizza&Pasta: hearty Italian dishes
  • Stretch the Noodle: flavorful Asian eats
  • Moonlight Mediterranean: various bites including gyros and hummus
  • La Pinata Takos: delicious Mexican pod

Read More: The Best Portland Tattoo Artists

Enjoy Portland’s Nightlife 

Portland’s unique vibe doesn’t fade when the sun goes down. In fact, there’s a mix of nightlife including dance clubs, karaoke, and alcohol-free fun. Here are some noteworthy spots for happy hour, music, and more.

Portland is filled with many opportunities for fun at night! Check out this full guide.

Day Two in Portland

We’ve got another entertaining day coming your way to finish off your weekend in Portland. Check out stylish cafes and shops and spend some time with nature.

Cafe Hop and Vintage Shop on Division Street

division street portland oregon

Division Street is one of Portland’s trendiest neighbourhoods where you can easily wander for hours. This area spans about 50 blocks and is filled with things to do and see. Here are a few noteworthy stops to make.

Visit the Portland Japanese Garden

Escape the city while staying close by and enjoy nature in this tucked-away garden. The Portland Japanese Garden is beautiful all year long. Stroll through 12 acres of gardens, intimate walkways, and an authentic Japanese Tea House. It also provides a scenic view of Mt. Hood.

Take a Portland Food and Craft Ale Tour

With over 70 breweries, Portland is a beer-lover’s paradise. Even if you aren’t a craft beer fanatic, a Portland food and craft ale tour is a unique experience. Tours provide insight into the city while taking you to the best breweries, too. 

There are tons of Portland beer tours and here are a few favourite options.

  • Craft Brew Tours: This tour takes you on a 3-stop journey. Learn about and taste a few of Portland’s specialties: coffee, donuts, and beer.
  • Brews Cruise: Pedal through the Pearl District and the historic Old Town while stopping to enjoy delicious beers at local breweries.
  • Microbrewery Tour: This evening bus tour lets you sit back and relax while you learn about the micro-brewing process. The bus stops at local breweries for you to sample beers. 

Where to Stay in Portland, Oregon

You can’t really go wrong in any area of Portland. Most of the city offers so many things to enjoy. However, we know it helps to have some guidance given that Portland is a big city with so many options. Popular neighbourhoods for travellers include Downtown, Hawthorne, Pearl District, and Nob Hill.

Here are some accommodations worth checking out.

Crystal Hotel

Located close to Portland’s city centre, Crystal Hotel is near many attractions including Powell’s Bookstore. Each room is eccentric and themed after a famous song. There’s a cafe, bar, and saltwater pool at the hotel. In the evening, enjoy live performances. If you’re travelling with a furry companion, it’s also pet-friendly.

Dossier Hotel

This trendy, modern hotel is also located close to Downtown surrounded by restaurants, shops, and parks. The rooms at Dossier are comfortable and precisely decorated with art. The hotel features a bar, restaurant, and gym. 


These sophisticated hotels offer apartment-living vibes. They’re conveniently located throughout Portland’s popular areas. Barsala offers several locations throughout the city.

  • KoZ: Pearl District
  • Couch9: Pearl District
  • The Canyons: North Portland
  • The Nexus: Kerns neighborhood

Final Thoughts

A trip to Portland, Oregon makes for one of the best weekend getaways. We hope this guide will help you have a memorable experience. 

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