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

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 for 48 fun and delicious hours in the Portland area.

​Where to stay


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:


Getting Around

Portland has a great public transportation system! 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!





  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. 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 parts of the Portland area and a must see if you’re nearby! Unfortunately last summer 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.


    1. Portland Women’s Forum State Scenic Viewpoint or Crown Point Vista House (OPEN)
    2. Latourell Falls (OPEN)
    3. Angel’s Rest Trail (OPEN)
    4. Multnomah Falls (OPEN)
    5. Oneonta Gorge (CLOSED)
    6. Ponytail and Horsetail Falls (OPEN)
    7. Eagle Creek Trail (CLOSED)
  3. Grab a massive ice cream cone at East Wind Drive-In
  4. Visit the town of Hood River
    1. Lunch at Full Sail Brewing Company. There are a lot of breweries in the area if you enjoy beer!
    2. Walk around and explore the shops
    3. Grab coffee at Stoked Roasters
  5. Check out the Rowena Crest Viewpoint
  6. Drive back to Portland and grab dinner at Güero or Teote​​.
  7. If you want drinks after dinner, head to Multnomah Whiskey Library, which is a beautiful bar in downtown Portland. 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!







  • Our top pick: ​Drive to the Oregon Coast and visit Cannon Beach (1.5 hours each way from Portland). Check out our Weekend on the Oregon Coast guide for ideas!
  • Visit the beautiful Portland Japanese Garden
  • Do the 4T Trail, which is a unique way to explore Portland by trail, tram, train, and trolley!
  • Visit Cathedral Park to see the gorgeous St. John’s Bridge
  • Hike to Tamanawas Falls–3.3 miles, 597 ft elevation gain (~1.5 hours each way from Portland)
  • Visit Trillium Lake for a beautiful view of Mount Hood (~1.5 hours each way from Portland)
  • Chase waterfalls at Silver Falls State Park (~1.5 hours each way from Portland)


Ready to get weird in Portland?

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

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