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Portland is well established as the ‘hipster’ capital of the U.S.A and for good reason. Loaded with unique breweries, locally-owned shops, and food trucks throughout the city, it’s easy to understand while you’ll already be wishing you had more than one weekend to spend in Portland!
*Fun Fact: You’ll also love Portland because it’s one of the greenest cities in the world! You’ll often see people choosing to walk, cycle or rollerblade to their destinations. Portland locals LOVE spending time outdoors, often choosing to picnic in parks and spend their weekends’ hiking.
If you’re a first-timer in Portland I can assure you that this guide is going to help you make the most out of your short time there! Keep in mind, instead of giving you a minute by minute itinerary, I’ve instead decided to give you the best options to build your own itinerary for the weekend! Mix and match however you’d like to spend your time depending on the type of trip you’re after (if it was me I’d just end up spending the entire time eating…)
Where to stay in Portland
First things first, when you have a limited amount of time in a city, where you stay is more important than ever. Luckily Portland is well equipped with a public transportation system, so getting around without a car is a breeze.
If you’re looking for a central place to stay that’s close to both downtown and the waterfalls and outdoorsy activities that Portlandians love, then I would recommend staying in the southeast Portland district. Both Bluebird Guesthouse and Evermore Guesthouse are both in an ideal location, they are pretty affordable (hard to come by in Portland!) and they have great reviews from other travelers.
You can also stay in Downtown Portland, which is a better option if you don’t plan on leaving the city for any quick hikes or half-day trips during your stay (If you’re driving, keep in mind that you’ll usually have to pay for parking overnight and you won’t be able to find parking that easily). Hotels I recommend in downtown Portland include: The River’s Edge Hotel and Spa give off that Portland-esque charm, while The Benson has a vintage luxury feel to it. However these both cost around $200/night.
Finally and always my favorite option is to look at Airbnb. Usually, I recommend that people book on Airbnb so they can save money by cooking for themselves… I can promise you won’t want to do that in Portland. Portland has way too many good food options for that! You will still be able to find better prices and comfortable accommodations on Airbnb.
Where to eat in Portland
- Mother’s Bistro – A gorgeous restaurant that you’ll want to eat at for brunch and dinner! You can tell they’re menu is well thought out and all their food is fresh and delicious.
- Voodoo Donuts – Did you even visit Portland if you didn’t stop by the famous Voodoo Donuts? I don’t think so… (Fun Fact: You can also get legally married here!)
- Maurice – The PERFECT brunch spot.
- Bluestar Donuts – A great contender for best donut in Portland.
- Stumptown Coffee – You’ve probably heard of Stumptown if you’ve done any research about Portland at all. What I can tell you is that it totally lives up to its reputation. Most likely to be the best coffee you have in Portland.
- Salt & Straw– A MUST visit for your weekend in Portland. Get in line and be ready to fall in love with ice cream all over again. (I’ll be disappointed in you if you get any less than two scoops.)
- Cartlandia– Cartlandia is going to be the number one reason you decided to spend the weekend in Portland. You won’t find anything like it anywhere in the world. Cartlandia is home to 32 food carts. So go hungry and try lots.
- Bamboo Sushi – Bamboo Sushi is known for being one the first sustainable restaurants in the country (which fits in perfectly with Portland’s entire atmosphere!)
- Pok Pok – A Portland classic that had its roots in a food truck! This classic Thai twist will definitely satisfy your cravings.
- No Bones Beach Club – A Vegan restaurant with one of the best menus I’ve ever tasted. Make sure to have a helping of the cauliflower wings, the brunchos, huevos and don’t forget mimosas!
Oh no… did I mention too many places to eat at in just one weekend in Portland? Well as I hinted to above, Portland is the kind of place where you are going to want to be eating all the time. Any of the above-mentioned restaurants and coffee shops that you try will not disappoint. One thing that Portland prides itself on is amazing, high-quality food.
What to do in Portland
Now let’s break down the best things to do in Portland (because we all need a break from eating, of course).
You’ll find an amazing range of activities in Portland, many of which you’ll even be able to enjoy completely for free. Here are my favorites (similarly to your food options, I recommend choosing however many of these fit into your weekend itinerary).
- Powell City Books – Powell’s is the largest used bookstore in the US (maybe the world?) and while it’s not quite as big as a city, it does take up the entire city block in Portland. This is a unique bookstore that even has a map to help you navigate the rows and rows of books. Make sure to leave extra room in your suitcase because I’ve never known anyone to walk into Powell City Books and walk out empty-handed.
- Take a free walking tour of Portland – Free walking tours are amazing for seeing as much of a city as possible in the shortest amount of time (like just a weekend trip for example!). I usually recommend taking a walking tour on the first day so you can plan the rest of your trip from what you learned and saw already.
- Take a wine tour – I recommend taking a tour with the Willamette Valley Wine Tour. You’ll usually visit three wineries: Rex Hill, Erath, and Stoller Estates. All wineries are breath-taking but as you’ll quickly learn, the Stoller Estates as an award winning tasting room.
- Craft your own brewery tour – Along with amazing wine and coffee, Portland is also well known for its local breweries. Choose a neighborhood and start your own brewery tour! You’ll be able to walk or take public transportation between destinations. It’s a great way to see the city and taste tons of unique beers you won’t find anywhere else.
- Lan Su Chinese Garden – This is a bit of a hidden gem in Portland. It’s also the most authentic Chinese garden outside of China! It costs $12.95 for general admission or $9.95 for students. (Fun tip: Post a picture of yourself there on your Instagram and see if people think you’re in China!)
- Watch the sunset at St. Johns Bridge – You might not know this but Portland is home to 12 bridges and each one is more beautiful than the last. It’s hard to argue that any are more beautiful than St. Johns Bridge at sunset. Make sure to check it out and let me know what you think!
- Wander through the Japanese Gardens – If beautiful gardens are your thing then Portland is your city. The Japanese Gardens are a beautiful escape for the hustle and bustle of the city and a great place to walk off your second lunch to make room for dinner!
- Visit Columbia River Gorge – just east of Portland, you’ll find waterfalls and hikes in the Columbia River Gorge! Whether you’ve got the whole day to spend or just wanted an easy hike to escape the city, you’ll find it all here.
As I’m sure you’ve realized with the length of this guide, Portland is an amazing city with lots to offer its visitors. While there’s a lot you can do there, it’s also a great city to visit on a weekend. You can choose to jampack your itinerary with everything I’ve mentioned above or you can take it easy, just eating and walking your way through the city.
Either way, I can promise that spending the weekend in Portland will not disappoint and I hope this guide helps you to plan your trip!
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