The ultimate guide to Portland in a weekend

Portland in a weekend

Ah, Portland in a weekend! Iconically weird and lovably quirky, it’s one of the most popular cities in the Pacific Northwest. Home to hipsters and amazing coffee, there’s plenty to explore in Portland. So, if you’ve only got two days to see the city, you’ll want to plan out the itinerary.

Here, we’re sharing when to visit, the best places to stay, things to do, and where to eat. Who knows – after reading this, you might consider extending your trip a few extra days!

When to visit in Portland

Portland has weather that you’d probably expect from the Pacific Northwest. It’s often gloomy and rainy, which doesn’t equate to the best travel weather in most other cities. But you can still have an amazing weekend in Portland rain or shine.

Temperatures in Portland are mostly bearable and from June to September, you’ll have better odds of sunny skies. Still, the summer months might be more crowded with higher prices. Braving the weather means more time eating and drinking, chasing waterfalls, and getting cozy in some of Portlands best coffee shops.

Where to Stay in Portland

Whether you want to be in the middle of the action or you’re ok with being on the outskirts of town, there’s accommodation just for you in Portland.

The Nines is where to stay for luxury and class, just off Pioneer Square. Bluebird Guesthouse and Evermore Guesthouse are also great options if you want to stay in southeast Portland for its proximity to both the downtown area and outdoor experiences.

River’s Edge Hotel & Spa and The Benson are both located in downtown Portland if you’re planning to stay in the city. But, Airbnb is also another popular option for Portland visitors. When looking up Airbnbs or other home rentals, popular areas to should search for are:

  • Pearl District
  • Alberta Street
  • Mississippi Ave
  • Woodlawn

If you’re looking for a classic hotel room without much fuss, Kimpton Hotel Vintage Portland, Hilton Portland Downtown, or Hotel Eastlund are all comfortable options with great locations.

Things to Do

As a popular tourist destination, Portland has no shortage of things to do. Take a walk through the Japanese Gardens in the West Hills. Or, snap that Insta-worthy photo in front of the “Keep Portland Weird” wall or with the iconic St. Johns Bridge.

Go shopping on Union Way where you’ll find shops like Spruce Apothecary and Quin Candles. You also shouldn’t miss stopping into Powell’s City of Books for the largest selection of used books in the world. It’s a Portland must-do. If you pick up more must-haves than you bargained for, drop off your bags at a luggage storage shop so you can shop the rest of Portland without feeling like a pack mule.

As hipster central, there’s a brewery on almost every corner. Take a brewery tour with Brewvana or Brew Cycle. Or, check out Portland’s local breweries on your own. There’s Base Camp Brewing Co., The Commons, Migration Brewing, Deschutes Brewing (a crowd favorite), Rogue Distillery, and more.

As much as there is to do in the city of Portland, nature-lovers will also have plenty to experience. Explore the outdoors at Forest Park and Washington Park. Then, as luck would have it, east of Portland is the Columbia River Gorge which has stunning waterfalls such as Multnomah Falls, Wahclella Falls, Latourell Falls, and Lower Oneota Falls.

Hit the town for a bit of nightlife in Portland. Bit House Saloon or Multnomah Whiskey Library are both unique and memorable ways to spend an evening. Or head to Bible Club, a speakeasy that will make you feel rebellious (in the best way)

Other popular nightspots like Killingsworth Dynasty, Radio Room, and Hale Pele. Plus, there’s Doug Fir which is a bar and music venue making it a great place for a night on the town.

The Kennedy Soaking Pool and Portland’s Saturday Markets come highly recommended and you may even stop my Pittock Mansion to take in the views of Portland from above.

Places to eat in Portland

In Portland, it’s sacrilegious to eat at a chain restaurant. With so many incredible independent establishments for every craving, eating in Portland is a unique experience all its own.

Let’s start with breakfast (as you do). Mother’s Bistro serves classic homestyle breakfasts that will remind you of your own mom’s kitchen and Pine State Biscuits offers delicious breakfast foods you won’t want to miss.

If you’re not much of a breakfast person, that’s ok. But in Portland, you won’t want to skip the coffee. Stumptown Coffee is the place to go for iconic Portlandian coffee. However, other heartwarming options include Coava Coffee Roasters, Good Coffee, Heart Coffee Roasters, or Sterling Coffee Roasters for a classic Portland latte.

Surprisingly, Portland also has its fair share of unbelievable donut shops. No one’s quite able to come to a consensus about which is best but the leaderboard shows both Blue Star Donuts and Voodoo Doughnut. Why not try them both? You’ll also find good donuts at 180 Donuts and Pip’s Original Doughnuts and Chai.

Check out Portland’s iconic food carts such as Portland Mercado for Mexican essentials or Central Eastside Food Carts offering international cuisines. In fact, Cartlandia is a full food cart village with 32 establishments that will knock your socks off.

Budget-friendly restaurants in Portland include Nong’s Khao Man Gai, Rontoms, The Sundra, Life of Pie Pizza, and Portland Penny Diner. But, if you’re ready to put on your fancy pants and splurge on dinner, head to St. Jack, Paley’s Place, Andina, or Le Pigeon.

Pok Pok offers Thai food with a modern twist (and it started as a food cart!) while Bamboo Sushi is the place to be for a sushi meal.

For dessert, there are a few spots you should try. Fifty Licks or Salt & Straw has some of the best ice cream flavours in the country. Or you might head to Sugarpine Drive-In for delectable sweet treats only Portland could provide.

Whether visiting your trendiest friend from college or you’ve chosen Portland as your girl’s weekend vacation destination, this city won’t disappoint. As you can see, it’s got some incredible things to do and unique food spots that will make you wish you’d stayed longer.

So, throw on your beanie and just try not to become a coffee snob. Portland is about to change your life!

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