Famous Old Town Portland Oregon neon sign on May 05, 2014 in Portland, Oregon. The sign faces westbound traffic as it enters downtown Portland coming across the Willamette River.

Best Things to Do In Portland

BY Fifty Grande Editors | August 31, 2020

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Portland? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Portland?”

 

We’ve all got that one friend who has an out-there hobby, listens exclusively to 8-track tapes and dresses ironically, though she/he doesn’t always seem to have a firm grasp on what that really means. Just like that guy from high school, we love Portland for its unique charm and keep-you-on-your-toes attitude. The city embraces peculiarity and celebrates eccentricity, qualities that produce its world-class cuisine, art and entertainment. This city might seem weird, but it also doesn’t care. It strives for quirkiness (see: “Keep Portland Weird” slogan). Between the food carts, fern-crested waterfalls, diehard cycling commuters and free-flowing PBR, you’ll embrace it too. Here’s how to explore the best of Portland right now:

You’re here for food carts

Like whales, Portland food carts come in pods. Unlike whales, they’re delicious and basically everywhere. These pint-sized eateries serve up some of the city’s boldest and most inventive food. You’ll find everything from bulgogi burritos to shawarma to Latin chicken, served up fast. 

Cartopia sign in Portland
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Cartopia sign in Portland.

Cartopia

1207 SE Hawthorne Blvd, Portland, Oregon, USA

Southeast Portland’s premier late-night food cart roundup. Chicken & Guns and Pyro Pizza are consistent local faves.

Prost Marketplace in Portland
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Prost Marketplace in Portland

Prost! Marketplace

4237 N Mississippi Ave, Portland, OR 97217, USA

Grab Indian fusion from Desi PDX or BBQ from Matt’s, then enjoy it with a half-liter of Kölsch or Weissbier and a soccer match on Prost!’s inviting patio.

You’re also here for Pok Pok

UPDATE: As of November 1, 2020, Pok Pok is officially closed for good according to a Facebook post from owner Andy Ricker.

Pok Pok started as a grab-and-go thai “street food” spot and became renown for it’s Vietnamese wings, one of Portland’s most iconic must-have meals. The resto garnered tons of national praise, expanded in Portland and beyond, and chef/restaurateur Andy Ricker won the 2011 James Beard Award for Best Chef: Northwest. Ricker downsized Pok Pok’s Portland footprint due to a variety of factors after Covid hit. But this location is open (and potentially Pok Pok Wing in Southeast). 

Pok Pok in Portland
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Pok Pok in Portland

Pok Pok

3226 SE Division St, Portland, OR, USA

UPDATE: As of November 1, 2020, Pok Pok is officially closed for good according to a Facebook post from owner Andy Ricker.

 

Find your inner adventurer

When you’re exploring its culinary offering and reveling in Portland’s uniqueness, it’s easy to forget that the city is surrounded by nature.

Vehicles drive through a stone tunnel leading to the entrance of Forest Park, the largest park in Portland, Oregon.
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Vehicles drive through a stone tunnel leading to the entrance of Forest Park, the largest park in Portland, Oregon. Shutterstock

Forest Park

Forest Park, Portland, OR, USA

Forest Park is one of the largest urban parks in the United States with more than 80 miles of hiking trails. It’s an in-town getaway for hikers, mountain bikers, dog walkers and trail runners. Nestled among the lush ferns and moss is Pittock Mansion, a Renaissance-style chateau built by the Portland publisher Henry Pittock.

Lush Landscape of Columbia Gorge National Scenic Area
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Lush Landscape of Columbia Gorge National Scenic Area. Shutterstock

Columbia River Gorge

Columbia River Gorge National Scenic Area, Forest Service Office, Wasco Street, Hood River, OR, USA

Follow the Columbia River east and you’ll find several waterfalls worth chasing. The tallest and most popular is Multnomah Falls, but you should also stop at Horsetail Falls, Bridal Veil, Shepperd’s Dell and Latourell Falls — all stunning waterfalls in the same proximity. 

Mt. Hood panorama and downtown Portland Oregon buildings. Shutterstock
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Mt. Hood panorama and downtown Portland Oregon buildings. Shutterstock

Mt. Hood

Mt Hood, Oregon, USA

If you fly into PDX or drive east on 84 you can’t miss Mt. Hood’s snow-capped peak standing over the city. Just more than two hours from downtown Portland, this is the perfect day trip for trail-hungry hikers. Mountaineers can go for the summit, but the foothills offer plenty of moderate trails with stunning views of the peak. Or just drive the Mt. Hood Scenic Byway to take in its majesty from the road.

Ascend to hop heaven

The Pacific Northwest is the worldwide leader in hop production. Like a citrusy bite on your ale? You can thank Oregon. With so many hop varieties nearby, Portland breweries produce some of the best IPAs you’ll ever have, and there’s no shortage of craft beer brewers doing it — 117 breweries in the Portland Metro Area. Ecliptic, Great Notion, Wayfinder, Ruse, Upright and Breakside are all excellent choices. 

Great Notion Brewing in Portland, OR.
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Great Notion Brewing in Portland, OR.

Great Notion Brewing

2444 NW 28th Ave, Portland, OR 97210, USA

This is the place for hazy IPAs and barrel-aged sours. And check out the fish tacos. (There’s a few locations)

Wayfinder Beer in Portland, OR
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Wayfinder Beer in Portland, OR

Wayfinder Beer

304 SE 2nd Ave, Portland, Oregon, USA

Exceptional German-style beers in the industrial district. Definitely try the “Twin Peaks”-inspired Black Lodge sandwich. 

Upright in Portland, OR
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Upright in Portland, OR

Upright Brewing

240 North Broadway, Portland, Oregon, USA

Specializes in small-batch, farmhouse-style ales on tap and by the bottle. 

Cool places to stay

Portland has a knack for converting old buildings into hip hotels. For example…

The Jupiter Hotel in Portland, OR.
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The Jupiter Hotel in Portland, OR.

The Jupiter

910 East Burnside Street, Portland, OR, USA

Repurposed from a midcentury motor inn, The Jupiter connects its guests directly to Portland’s music and art scenes with an in-house gallery and a live music venue (the Doug Fir Lounge) on the same property.

McMenamins Kennedy School in Portland, OR
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McMenamins Kennedy School in Portland, OR

McMenamins Kennedy School

5736 NE 33rd Ave, Portland, Oregon, USA

It’s a converted elementary school that contains multiple bars and restaurants, a movie theater and a soaking pool. 

Where to see a show

Check out two of Portland’s most unique venues.

Mississippi Studios in Portland, OR.
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Mississippi Studios in Portland, OR.

Mississippi Studios

3939 N Mississippi Ave, Portland, Oregon, USA

A northeast Portland spot that’s unpretentious and intimate with great acoustics and plenty of up-and-coming talent. They’ve got local beers on tap and the adjacent Bar Bar has great burgers.

McMenamins Crystal Hotel and Ballroom in downtown Portland Oregon off of Burnside. Microbrew craft beer restaurant
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McMenamins Crystal Hotel and Ballroom in downtown Portland Oregon off of Burnside. Microbrew craft beer restaurant. Shutterstock.

McMenamins Crystal Ballroom

1332 W Burnside St, Portland, Oregon, USA

The Crystal Ballroom, renovated out of the historic Coalition Hall, hosts bigger acts (including Oregon bands like Everclear and The Decemberists). But the most interesting part? The floor bounces. 

Binge on five stories of books

A cornerstone of the city’s literary community. Did we mention that it’s gigantic?

Powell's Books In the city of Portland, Oregon. Powell's Books is the largest independent bookstore in the world.
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Powell's Books In the city of Portland, Oregon. Powell's Books is the largest independent bookstore in the world. Shutterstock

Powell’s Books

1005 W Burnside St, Portland, OR, USA

Powell’s is the world’s largest independent bookstore, with five stories of new and used books at their downtown Portland location. They often host cool readings and book signings with bestselling authors, so check their schedule before you go. 

Eat fun and weird donuts

You’re probably familiar with Voodoo Doughnuts, the slightly morbid shop where you can get a doughy pastry shaped like a voodoo doll, complete with jelly blood. But the PDX donut scene goes much deeper: Check out shops like Heavenly Donuts, Blue Star Donuts, Delicious Doughnuts, NOLA Doughnuts and Donut Queen.

Heavenly Donuts in Portland
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Heavenly Donuts in Portland

Heavenly Donuts

1915 N Lombard St, Portland, OR, USA

Classic comfort donuts like Long Johns, fritters and old fashioneds. Simple but effective, and perfect with some black coffee. 

Blue Star Donuts in Portland, Oregon
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Blue Star Donuts in Portland, Oregon

Blue Star Donuts

672 #2 S Gaines St. Portland, OR

They’re not afraid to experiment with flavors — like their blueberry bourbon basil, orange olive oil, or passionfruit cocoa nib donuts.

Get your garden on

Western Oregon winters are essentially one long drizzle, but it does wonders for Portland’s greenery. This temperate climate is perfect for lush, flower-lined gardens.

Portland Japanese Garden in Portland, OR.
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Portland Japanese Garden in Portland, OR. Photo: Shutterstock.

Portland Japanese Garden

611 SW Kingston Ave, Portland, Oregon, USA

Trickling water. A breeze through the pagoda. Koi fish circling. The Portland Japanese Garden might be a common tourist spot, but it still exudes peace. Trek to Washington Park to visit and you’ll find cascading ponds, manicured bonsai trees, an authentic teahouse and traditional Japanese architecture.

Rose Garden in Portland, Oregon. Photo: Shutterstock.
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Rose Garden in Portland, Oregon. Photo: Shutterstock.

International Rose Test Garden

400 SW Kingston Ave, Portland, Oregon, USA

It’s across the street from the Japanese Garden and houses 650 rose varieties (there’s a reason for the “Rose City” nickname).

Wander these nabes to get a sense of the city

Every corner of Portland’s neighborhoods has its own persona, but if you need somewhere to wander and soak up the atmosphere, try these.

Sign in the Alberta Arts District in Portland, Oregon.
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Sign in the Alberta Arts District in Portland, Oregon. Photo: Shutterstock.

Alberta Arts District

Alberta Arts District, Portland, OR, USA

This NE Portland neighborhood is all of the city’s culture, taste and yes, weirdness in a microcosm. Here, business owners and young hipsters mingle at some of the coolest bars and coffee shops around. You’ll likely find a line around the corner for Salt & Straw ice cream (but it’s worth it), and locals sipping sake at Zilla Sake House or mezcal at Teote Mezcaleria. Plus, Alberta houses boutiques selling local goods, art galleries showcasing local artists and makerspaces where anyone can dive into DIY crafts.

Barista coffee shop in the Pearl District of Portland, Oregon. Pic: Shutterstock..
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Barista coffee shop in the Pearl District of Portland, Oregon. Pic: Shutterstock.

The Pearl District

Pearl District, Portland, OR, USA

The Pearl District is a hot spot for trendy restaurants and repurposed warehouse spaces. And on the first Thursday of every month, it hosts one of the city’s most lively art celebrations. Artists and dealers gather here to showcase and sell their work. Galleries stay open late with live music, free wine and snacks. 

 

Take a boozy trip down Distillery Row

Whether you need to restock your liquor cabinet or just want some top-shelf cocktails, Distillery Row has you covered. Grab a Distillery Row Passport and sip your way down the line. 

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New Deal Distillery

900 SE Salmon St, Portland, OR, USA

They make all kinds of liquor, but specialize in vodkas and gins. Feeling bold? Try the Hot Monkey Vodka, which is made with hot peppers.

House Spirits Distillery
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House Spirits Distillery

House Spirits Distillery

65 SE Washington St, Portland, Oregon, USA

Now partially owned by actor Ryan Reynolds, their Aviation American Gin put them on the craft distilling map.

Eastside Distilling in Portland, Oregon.
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Eastside Distilling in Portland, Oregon.

Eastside Distilling

1001 SOUTHEAST WATER AVENUE, SUITE 390, PORTLAND, OR

Don’t miss their whiskey that’s infused with marionberry, a type of blackberry first cultivated at Oregon State University.