Ready to get weird? Then let’s head to the city where locals advocate to “Keep Portland Weird.” Portland is a bustling metropolis and Oregon’s biggest city. It’s got all the hallmarks of a big city—an innovative culinary scene, hip neighborhoods, a thriving music scene and breweries on every corner—and is in close proximity to the great outdoors.

It’s no wonder why everyone loves Portland! There’s a little bit of everything on offer in Portland, and if you go during dry season, you’ll experience long sunny days. Sound like a city too good to be true? Well, I can’t write a Portland City Guide without mentioning the fact that it rains A LOT. Like, 9 months out of the year.

The redeeming factor is that the city gets entrenched in 50 shades of green and it’s absolutely breathtaking.

In this Portland City Guide, I’m covering everything you need to have the absolute best trip to Portland. From unique sights, delectable eats and eclectic nightlife, let’s get hip and weird in Portland, Oregon.

Why You Should Go

Where do I start? If the breweries, artisanal cafe’s and varied food doesn’t appeal to you, there’s also amazing vintage shops, off-beat attractions, museums, gardens, waterfalls, and more. There’s literally something for everyone in Portland, which is exactly why you should visit. Whether you want a tranquil getaway in the great outdoors, or to get on the brewery scene and listen to local artists, you can tailor your visit to Portland to your preferences.

What To See in Portland

Portland is filled with unique neighborhoods, markets, and sights. Here’s a look at some of the most popular, unique and fun attractions to see in Portland.

Portland Saturday Market
One of Portland’s top tourist attractions is the Portland Saturday Market. Stroll this massive outdoor market and peruse locally made arts and crafts, try exotic foods and listen to live music, all set amidst the charming backdrop of Historic Old Town Portland. Basically, it’s a must see!

Underground City Tour Of Shanghai Tunnels
If you’re looking for a unique experience in Portland, I highly recommend taking an underground tour of the Shanghai Tunnels. Set beneath Old Town Chinatown, these tunnels are a group of large passageways. You’ll get insight into Portland’s scandalous history—including crime facts, controversial myths and remnants of Portland’s biggest sins. If you’re big on crime history and offbeat attractions—this one’s for you!

Wander The Pearl District, Especially On First Thursday
If you time your trip right, you’ll get to enjoy the bustling and artsy scene of Portland’s First Thursday in the Pearl District. Stroll the eclectic streets exploring local art exhibitions. Even if your trip doesn’t align with First Thursday, the Pearl District is the nexus of art, culture, and the best bars and restaurants. Ultimately, whatever you need, you can find at the Pearl District. Not to mention this neighborhood is in the heart of Downtown Portland, making it a perfect stop on your hop through Portand’s best.

Spend An Afternoon In Powells Books on Burnside
If you’re a book lover, you can’t miss Powells City of Books, which happens to be the world’s largest independent bookstore. This is no meager mom and pop shop, Powells literally houses and entire city block full of rare, unique, new and sold-out prints of books. The grand total? 1 million books! But you don’t have to be a bookworm to appreciate the sheer volume and size of Portland’s prized book store which just so happens to be located on Burnside, a major intersection where old Portland meets new.

Give yourself a lazy afternoon to explore the halls of this awe-inspiring bookstore, or sip on a latte and cozy up to a good book.

Take A Stroll At Tom McCall Waterfront Park
One of the best things about Portland is the Waterfront. Here you can take a break from the big city, nestle beneath a shaded tree, take in the views and enjoy the gorgeous fountains. Locals and tourists come to Tom McCall Waterfront Park for respite, activity and a little oasis. Perhaps the best part of the waterfront is that it gives you a glimpse of nature in the heart of downtown. This is perfect if you’re planning a day of exploring but want time to mellow out in a beautiful park. Stroll the 1.5 mile greenbelt which stretches along the sparkling Willamette River.

Visit the Rose Garden and Japanese Garden

Another gorgeous dose of nature awaits you at Portland’s beautiful gardens. Visit the Rose Garden in Washington Park to enjoy over 10,000 rose bushes! To see the roses in full bloom, plan to visit between April and October.

Another beautiful garden is the Portland Japanese Garden. Explore 12 sprawling acres of scenic waterfalls, views and gardens. This tranquil haven is a beautiful timeout from the busy streets of Portland. Take a break to enjoy a cup of tea at the tea house, learn about Japanese history and enjoy a fusion of art, nature and tranquility in this authentic Japanese garden.

Where You Should Eat

With all this exploring, you’re bound to build up an appetite! Good thing you’re in one of the most diverse food meccas in the U.S. From exotic to quirky to world-class, let’s explore some of Portland’s finest eateries.

Voodoo Doughnut if you are not gluten Free
You may have to live under a rock to have not heard of Voodoo Doughnuts in Portland. People literally travel to Portland to wait in line for up to an hour for the sole purpose of trying one of these world-famous donuts. While I can’t say I’ve tried it personally due to my gluten-free diet, the line out the door and buzz about Voodoo makes it one of the top places to eat in Portland for a yummy snack. Good news for vegans—you can totally get down on some vegan donuts here.

Sample Food Carts
Food carts have come a long way in recent years, but in Portland, they’re an institution. Sampling the various food carts is an essential part of living in, and visiting Portland. As you drive through Portland, you’ll see corners and streets lined with food carts and stalls scattered throughout the city. Whether you stop for burgers at the 5th Avenue Food Cart Pod, or stop downtown for tacos, food carts are a must try on your trip to Portland. One of the most hip spots to visit is Cartlandia, a buzzing food cart pod in to sample artisanal burgers, exotic international fares, and sweet treats.

Insider Tip: if you want Voodoo doughnuts without the line—visit Cartlandia’s Voodoo truck to cross two Portland must-see’s off your list in one spot.

Explore Unique One Of A Kind Sodas At Rocket Fizz
A unique and quirky place to try is Rocket Fizz. Sample their collection of one-of-a-kind sodas, sweet candy’s and tantalizing desserts. If you love candy shops, then you’ll go nuts over Rocket Fizz. It’s such a unique place to sample tasty soda pop’s in a variety of flavors and no matter what mood you’re in, Rocket Fizz is sure to bring a smile to your face and bring out your inner child.

Explore the Vineyards and Countryside
Portland is nestled amidst the sprawling and picturesque Willamette valley. A lovely day trip from Portland awaits you, and in just a 40 minute drive you’ll be immersed in the sprawling Ponzi Vinyards. Tap into your inner wino at the Tasting Room. Or, explore the lush countryside at Smith Berry Barn, where you can pick berries, visit the nurseries and shop for local and fresh produce.

Check Out my GF Dining Guide
I’ve literally only scraped the surface of all the delicious foods on offer in Portland, OR. So, be sure to check out my dining guide for all the top Gluten free restaurants, breweries and bakeries in Portland!

Nightlife in Portland

Even after you’ve tuckered yourself out from the day’s activities, you’ve got to sample Portland’s thriving nightlife. One of the best things about Portland is that it’s a nexus for breweries, local music and creative arts scenes. Here’s a quick sample of Portland’s nightlife:

See A Show At the Crystal Ballroom
The Crystal Ballroom is one of Portland’s crown jewels. Located in one of Oregon’s token establishments, McMenamins, the Crystal Ballroom is a historic music venue in downtown Portland with grand chandeliers, vaulted and ornate ceilings, a floating dance floor and music hall highlighting all sorts of acts from country to hip-hop.

Hop Around To Different Breweries
Fun fact: The Portland Metro Area contains 117 breweries, with 77 located in the city of Portland. So, you can’t exatly visit this Brewery hotspot without sampling the local beers now can you? I didn’t think so. It’s super fun to hop around to the various breweries in Portland, each offering its own unique spin on beer. And with Portland ranking 8th in most breweries per capita in the U.S., you’ll not go thirsty here!

Get Familiar With the Local Arts and Music Scene
It’s no secret that Portland is artsy, but you’ll not find stuffy museums here. You can find live music every single night of the week in Portland. Whether you sit in for a night cap to listen to mellow music at a local pub, or want to let loose at a dub-step dance hall, there’s just something to do anywhere you turn. And even after hours, when most cities close the doors to their art halls and museums, you can enjoy the Oregon Symphony, Portland Museum or Shnitzer for nightly acts, events and exhibitions.

Where To Stay in Portland

On your trip to Portland, you’ll want to be centrally located to easily access all the sights and attractions, which is why I recommend staying downtown. An up and coming alternative is SE Portland.

Kimpton
If you’re traveling with your furry friend, checkout Kimpton Hotels. We stayed at the Kimpton Hotel Vintage and it was just steps away from all the downtown Portland sights to see.

Snag a good deal on hotel tonight
To easily browse countless listings throughout Portland, I recommend grabbing the best deal on Hotel Tonight, a travel app that helps you find the best discounts on hotels in Portland.

When You Should Go

As I mentioned before, the rain is very real in Portland. In fact, it rains about 9 months out of the year in Portland. So, the best time to visit Portland and stay dry is summer through Fall. Summer in Portland is absolutely gorgeous. Temperatures can get high, but the city comes to life and there’s no shortage of fun things to do and see. Fall is also a beautiful time to visit just before the rainfall, and the myriad of trees scattered throughout Portland begin to change and shift into beautiful autumn colors. If you want picturesque Portland, visit in the Fall.

Getting Around

There’s no way around it—Portland is a big city. However, there are multiple options that make getting around Portland super easy. The most popular transit option is with Uber or Lyft. However, if you want to explore Portland like a local, a fun way to explore Portland’s neighborhoods is to rent a bike. Other ways to get around Portland include the Max Light Rail which provides excellent access to downtown Portland.

How To Get There

Portland International Airport (PDX) is the most direct airport to Portland, but it’s about a 25 minute drive to downtown Portland without traffic. With traffic, it’ll take 40-60 minutes.

Ready To Go To Portland?

As you can see, there are so many amazing things to do, see and eat in Portland, it’s no wonder it’s become a major tourist destination! I hope this guide helps you experience the fun and quirky heart of Portland that really sets itself apart from any other city in the U.S.

With all the music, food, and beer—you’ll never get bored in Portland!

About Me:
I am an IIN Certified Health Coach helping people heal from Lyme, Mold and Autoimmune Disease. Learn more about my journey and how we can work together.

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