Portlandia with a Local: A Weekend Getaway to Portland, Oregon

Portlandia with a Local: A Weekend Getaway to Portland, Oregon

One of the most popular requests I get is for tips and suggestions on what to do here in Portland, Oregon. I’m very grateful to live in the heart of the city, on the east side of the Willamette River, within walking and biking distance of superb restaurants, drinks of all varieties, and lots of things to do.

I’ll attempt to distill my Portland favorites down into one manageable page here for your next weekend getaway to Portland. I’ve paired my ideas with some of my favorite Instagram moments, to give you a feel for what Portland really looks and feels like.

weekend getaway to portland oregon

Classic Portland Experiences to See or Skip?

I’d like to start out by just addressing some of the classic Portlandia moments, because I know you’re going to ask me about them.

Powell’s Books: See. Spare a couple of hours here just to browse the aisles and aisles of books. It’s such a joy and one of my favorite treats. There’s an in-store coffee shop and you can bring books there to look at before purchasing.

Voodoo Donuts: Skip. The best donuts in Portland are Blue Star Donuts. If you are downtown and in need of a sweet treat, go across the street to Blue Collar Baking for handcrafted bundt cakes and cookies. Their motto is self-explanatory: “we’re not afraid of butter.”

River Cruise: See. I go on the Portland Spirit champagne brunch cruise every year for my birthday. I wouldn’t call it the best city boating experience I’ve ever done, but it’s definitely decent and fun.

overlooked portland

Overlooked Portland Treasures

One of the best things about Portland are the neighborhoods. This is where the real “Portlandia” experiences that you are no doubt looking for will happen. Two of my favorite neighborhoods (I’ll use their street name, for simplicity):

leaves 'arch'

N Mississippi Street: Lots of quirky shops, food, drink. I don’t go here often but when I do, I want to stop everywhere: the cute urban nursery, the old drugstore turned into a coffee shop, the salt and chocolate store (yes, really).

SE Division: Lots of new construction has transformed this neighborhood, not always in a good way. But there’s my favorite food cart pod (Tidbit), my favorite tea shop, a great wine bar, and the new shops popping up are a lot of fun.

There’s also lots of great food and shops on both SE Belmont and SE Hawthorne, and for art galleries you should head up to NE Alberta street.

ladds addition

And although Oregon is associated with rain, we have so many urban parks, you can’t miss a bit of nature while you’re here. My favorite is the Eastbank Esplanade, the path that runs along the river on the east side between the Steel Bridge and Hawthorne Bridge; you can run, bike, or walk.

city view forest partk

Slightly harder to navigate, but there’s also Forest Park, one of the largest urban parks in the country. If you want a sneak peek, check out the International Rose Test Garden, which will help you better understand the story behind why Portland is called the Rose City.


Where to Eat in Portland

I have to admit, this is a really difficult section to address, because Portland is, to be blunt, perhaps one of the best culinary destinations in the world, and I’ve been to many of the best restaurants in the world and the best culinary cities in the world. I can count on one hand the number of venues on my “never again” list; because Portlanders are foodies, restaurants with subpar food usually don’t make it long.

teote restaurant

I suggest you explore the neighborhoods, and use Google to guide you to food genres that appeal to you the most. Portland’s strengths are pizza, southeast Asian, and generally carbohydrate-heavy foods (think fries, tots, biscuits, pancakes, etc.)

portland food

Here’s my challenge for you while you’re here: 1) go to a food cart at least once, 2) dine with one of our James Beard award winners (good list here) one night, and 3) try a dish you would never get at home, such as arepas (Latin American), Korean, unique ice cream flavors, or exotic charcuterie. Then you’ll appreciate the true depth and diversity of Portland’s culinary talents.

wine in portland oregon


One of my favorite things to do in Portland is go wine tasting. You’ll want to check out my previous roundup of the Best Portland Urban Wineries and pick a couple to check out during your visit. Pairings Portland is also a great local wine shop with lots of classes and events that are open to visitors. I strongly suggest flying into Portland on Alaska Airlines, because you can check a case of wine for FREE on your way home.

eastside distilling

We also have a lot of distilleries here! My faves would include New Deal Distillery (great vodka and ginger liqueur) and Eastside Distilling (fantastic bourbon and seasonal liqueurs). FYI, the Made in Oregon shop in the Portland airport carries several different local spirits, so if you don’t end up having room in your checked luggage, you have a second chance here.

But Portland is mostly well-known for beer. Almost everywhere you’ll go you will find fresh local beers on tap. Some beer spots I like: Breakside Brewing in northwest Portland, Green Dragon in southeast Portland, and Bridgeport Brewing in northeast Portland. If you’re up for a beer adventure, pick up a copy of Hop in the Saddle and follow the self-guided beer-by-bike tours.

As for Portland’s other big export — coffee — you can’t go wrong, because we have local coffee brewing almost everywhere. Heart Roasters and Coava are my favorites.

sentinel hotel

Deluxe Portland Sleeps

Portland has a lot of options for getting a good night’s sleep — everything from AirBnB to a really tiny hotel. However, I’m a traditionalist; given my previous experiences with AirBnB, I’ll pick the boutique hotel any day. Sadly, most hotels are downtown, which I consider the least interesting part of Portland, so come ready to jump on a bus or bike. Here are my favorite Portland hotels:

The Sentinel: Luxurious but kitsch. Central location an easy walk to Powell’s, food trucks, and bus/train links. This is a very old hotel they remodeled just last year and they’ve done a great job with it. (View from balcony above.)

Hotel Vintage Plaza: Wine-themed accommodation in another very central location; you’ve got beer, chocolate, coffee, and wine on each side of this hotel. Another hotel that’s undergone excellent renovations and upgrades recently.

riveredge hotel

Riverplace Hotel: Waterside relaxation. I love this spot because you are in a fairly quiet part of the riverfront, still easily walkable to downtown sights, but there are cocktails in the lobby bar and a great wine bar just around the corner. Despite the highway crossing the horizon (pictured above), the view really is quite relaxing, and you’re right on the river path if you want to walk or bike in either direction.

pacific city dunes


If you happen to have an extra day or two in Portland, I strongly encourage getting out of town for the day if the weather suits. You can head to the Oregon Coast, one of the most magical places on earth. Here are my favorite Oregon coast spots.

You could also go east and explore the Columbia River Gorge and Multnomah Falls — probably one of the easiest and most popular Portland daytrips.

Or you could head south into wine country. The Willamette Valley is filled with so many great wineries, I can’t pick my favorites. You’ll just have to come back and visit us again.

Portlandia with a Local: A Weekend Getaway to Portland, Oregon

Andy Hayes

Andy Hayes is the founder and creator of Plum Deluxe. He authors our award-winning weekly email newsletter, The Blend and curates our popular organic tea of the month club.

What Tea We're Sipping on Right Now

spiced cranberry tea

Holiday Embrace Herbal Tea (Cranberry Chai / Orange)

We love this spicy cranberry tea shared with family and friends during the holidays. $7/oz.

Add to cart

Candy Cane Herbal Tea (Vanilla / Peppermint)

A tasty and invigorating treat. $7/oz

Add to cart

Chocolate Rosemary Caramel Herbal Tea

Savory and sweet - the perfect balance. $7/oz

Add to cart

Loose Tea Accessories + Teaware

Care Packages (Tea Gift Sets)


Sweets & Treats

Popular Tea Themes Right Now:
Fruit Flavored Tea, Any Dessert Flavored Tea, Our Best Floral Teas