A Weekend in Portland

A weekend in Portland Oregon | Portland Oregon itinerary | Portland Guide | Things to do in Portland | Best food Portland | Where to eat Portland | Columbia River Gorge | Portland hikes | Where to stay in Portland | Portland Things to Do | Portland Food

Looking to spend a weekend in Portland? We’re sharing a detailed Portland itinerary and guide with everything you need to know before you visit including where to stay, what to eat and drink, the best things to do in Portland, and more! Ready to plan your own Portland adventure? Keep on reading!

Just 3 hours from Seattle lies the quirky, fun, and delicious city of Portland. We love spending a weekend in Portland! It reminds us of a hybrid of Seattle and our hometown of Austin. Similar to Austin, it is proud of its title of being a “weird” city, is home to tons of great restaurants and food trucks, and has an artsy culture/vibe. 

We always have a blast exploring the beautiful outdoors, checking out unique shops, eating at cheap, local eateries, and drinking tons of coffee.

Heading to Portland soon? Here’s our go-to itinerary and guide with all of our favorite things to do in Portland if you only have 48 hours!

Note: this guide contains affiliate links, which means that if you use the links provided and make a purchase, we get a small commission at no extra cost to you. We will only ever recommend products we truly love, actually use during our adventures, and think you can benefit from too!

When to visit Portland

Portland Weather

While the temperatures are bearable year round in Portland and snow isn’t a huge issue in the city, Portland, similar to the rest of the Pacific Northwest, can be a bit rainy during certain times of the year.

If you want lots of sunshine, the best time to visit Portland is between June-September (May and October can also be great, but sometimes more of a gamble). The temperatures are perfect, the sun is out, and there is way less rain. The snow in the mountains is also melting, which means that more hikes are accessible.

However, if you don’t mind getting a tiny bit wet, we have visited Portland during rainier months and have always had a blast! There is still so much to do when it rains, like chase waterfalls, eat more food, drink more coffee, and wander around shops. You could even go visit a ski resort! The rainier months will definitely be less busy and cheaper, so if you don’t mind some gloom, the late fall, winter, and spring may be a great time for you to visit!

Getting to Portland

PDX Carpet

Portland is home to Portland International Airport (PDX), which is one of our favorite airports in the US! It has tons of local eateries inside, which we love, plus some ugly carpet that has become a popular thing to photograph on Instagram.

PDX is located about 13 minutes Northwest of the city and is about a 20 minute drive or 55 minute MAX ride to downtown Portland.

Getting Around Portland

Portland Oregon

Portland has a great public transportation system, like the MAX light rail! Between that, walking, and Uber/Lyft, you can easily get around the city. However, if you want to explore the Columbia River Gorge (on this guide) or any nature spots outside of the city, we highly recommend renting a car for a portion of your trip!

​Where to stay in Portland

A weekend in Portland Oregon | Portland Oregon itinerary | Portland Guide | Things to do in Portland | Best food Portland | Where to eat Portland | Columbia River Gorge | Portland hikes | Where to stay in Portland | Portland Things to Do | Portland Food


Similar to our other guides, we highly recommend staying at an Airbnb while in Portland. There are many neighborhoods in Portland and here are some options of where you could stay:

PS: If it is your first time staying at an Airbnb, click this link to get $40 off your first stay!


If you would rather stay at a hotel, here are some good options:


  1. Get breakfast at Pine State Biscuits. We recommend the Reggie Deluxe! If you’re looking for a fancier breakfast experience, check out our “if you have extra time” section!
  2.  You can’t visit Portland and not have coffee! Some spots to check out:
  3. Admire all of the beautiful roses at the International Rose Test Garden
  4. View Portland from above at the Pittock Mansion, which is a great quick and free stop!
  5. Explore the aisles of books at Powell’s City of Books, a Portland institution and the largest independent new and used bookstore in the world.
  6. Grab a doughnut at VooDoo Doughnuts or Blue Star Donuts (or both!)
    • VooDoo is an iconic Portland spot with fun toppings, while Blue Star is known for fancier gourmet doughnuts. There’s a battle over which is better, so we suggest trying both and deciding for yourself. 🙂
  7. Snap a photo in front of the Keep Portland Weird Wall and walk down to the waterfront to see the White Stag Sign.
  8. Lunch at Nong’s Khao Man Gai
  9. Spend the rest of the afternoon checking out some of Portland’s cool neighborhoods and streets, which are full of local shops, restaurants, and breweries. Some of our favorites include: Alberta Arts District (lots of fun murals!), Pearl District, Mississippi Avenue (Pistils Nursery is so cute!), Division/Clinton, Hawthorne.
  10. Dinner at Pok Pok or Por Que No?, both are delicious and two of our favorite places to eat in Portland!
  11. Enjoy delicious ice cream at Salt & Straw (multiple locations). This is one of the best ice cream shops we have ever been to!


  1. ​Start the morning with mini doughnuts and chai flights at Pip’s Original Doughnuts and Chai
  2. Spend the day driving and exploring the Columbia River Gorge
    The Columbia River Gorge is a GORGEous area just 30 minutes from Portland with tons of waterfalls, hiking, and scenic views. In our opinion, it’s one of the best things to do in Portland! Unfortunately in the summer of 2017, the Eagle Creek Fire tore through the area, making many beloved spots inaccessible for now. Our recommended list includes some of these spots, but we will mark them as closed and change their status once opened to the public again.
  3. Grab a sweet treat on your way back to Portland at Sugarpine Drive-In, an awesome little spot with sandwiches, salads, and soft serve sundaes.
  4. Head back to Portland. For dinner, check out Güero or Teote​​. Both are fast-casual spots with delicious food!
  5. If you want drinks after dinner, head to Hale Pele or Multnomah Whiskey Library, which is a beautiful bar in downtown Portland.
    For Multnomah Whiskey Library, walk ins are welcome, but it is a very popular spot, so expect a wait. While reservations are only technically available for members, they do have a Hall Pass where for $25/person, you can get a reservation without being a member. 

If you have extra time…

Have more than a weekend in Portland? Here are some other suggestions of things to check out!






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