A Weekend in Portland, Oregon Itinerary

Looking to spend a weekend in Portland, Oregon? 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!

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!

Watch how we spent an epic day eating and sightseeing in Portland here!

Looking for more things to do in Oregon? Check out these guides & videos:

Before embarking on your adventure, please review the Leave No Trace principles to ensure you leave every place better than you found it, so that others can enjoy these beautiful places for many years to come!

These seven principles include planning ahead and preparing, hiking and camping on durable surfaces, disposing of waste properly (pack out what you pack in!), understanding campfire rules and always fully extinguishing your fires, respecting wildlife, and being considerate of other visitors. 

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

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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:


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. Grab lunch at Nong’s Khao Man Gai, which is an awesome spot for Khao Man Gai, which is a chicken and rice dish from Thailand. It sounds and maybe even looks bland, but it’s SO good!
  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 Por Que No?, which is a great Mexican spot and one 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. We LOVE this place so much! Every flavor of doughnut or chai we have tried has been amazing. The owners care a lot about the community as well!
  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.

    There are many other spots to explore along the Columbia River Gorge, but this list is just our go-to list if we only have part of a day. If you have more time, we recommend stopping at some of the many other spots along the way (they are usually well marked!).
    • Portland Women’s Forum State Scenic Viewpoint or Crown Point Vista House (OPEN): These are super quick spots where you can just drive up, park, and soak up the views!
    • Latourell Falls (OPEN): 2 miles round trip, 643 ft elevation gain. The loop trail at Latourell Falls is pretty easy and quick and takes you by both Latourell falls and Upper Latourell falls! If you’re short on time, you could just visit Latourell falls, which is close to the parking area.
    • Angel’s Rest Trail (OPEN): 4.5 miles round trip, 1,476 feet elevation gain. This hike is pretty steep, but you’ll be rewarded with views of the Columbia River Gorge! It does get busy, so be prepared to share the trail.
    • Multnomah Falls (OPEN): This is a classic Columbia River Gorge stop and a must-do! You can visit the iconic view of the falls just a quick walk from the parking lot, but you can also walk up onto the bridge and up to the top of the falls (2 miles round trip, 823 feet elevation gain).
    • Oneonta Gorge (CLOSED): 1 mile round trip, minimal elevation gain. This hike is absolutely incredible! You walk through a gorge and creek bed (yes, in the creek!) to reach a beautiful waterfall at the end. You’ll have to climb over logs and walk through water, so we only suggest making this trek if you’re physically able and don’t mind getting wet.
    • Ponytail and Horsetail Falls (OPEN): 2.6 miles round trip, 610 feet elevation gain. We love this trail! It’s not too long of a hike and you get to see two waterfalls! But the best part? You can walk behind one of them (Ponytail Falls)!
    • Rowena Crest Viewpoint (OPEN): This quick overlook is located a bit farther from the other stops on this list, but it has views of both Washington and Oregon, the Columbia River, and a super cool horseshoe curve in the road (pictured above!)
  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!






Ready to get weird in Portland?

Pin this weekend in Portland guide to help plan your trip!

about us

Hi y’all! We’re Adam, Kathryn, and Kona, an adventurous married couple (+ pup!) living on the road in our self-converted sprinter van! You can often find us driving all around the US and Canada, scoping out the best coffee shops, eating tacos and ice cream (we’re a 5+ taco and 2+ scoop household), and enjoying nature.


affilliate disclosure

This website contains affiliate links from websites such as MileValue.com, Amazon.com, Booking.com, and Rentalcars.com. If you use the links provided and make a purchase, we get a small commission at no extra cost to you. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. We only recommend products we truly love, actually use during our adventures, and think you can benefit from too!


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