The slogan “Keep Portland Weird” can be seen throughout the city on various bumper stickers and signs. Is the City of Roses really as weird as it is made out to be?
We talked to Portland’s very own Christopher Chin, digital content creator and founder of the clothing brand Rude Mondays to get the inside scoop on the city.
Having been in Portland for the past five years Portland, Chris originally hails from sunny and warm Fort Lauderdale. Raised by two Jamaican parents, Chris brings a fresh perspective to the city.
According to Chris, the best things about living in Portland, are the “parks, people, and coffee”. As simple as it sounds, we have to agree. Portland has dozens of beautiful and scenic parks and coffee shops on every street corner. But what really makes the city special is its tight-knit community built on creatives.
Photos by Umit Aslan (@umit1010) and Christopher Chin (@septembermondays)
Chris really emphasized that it is the people in the city that make it so great. He describes it as: “very vibrant when it comes to the creative scene… Everyone here is a creative”.
Compared to other cities like New York or Seattle, Portland feels small. While being vibrant and modern, there’s a strong sense of community, relaxation, and warmth.
“Normal people live here, but (we are) “weird people” to outsiders,” says Chris.
Explore lively Portland like a local and check out some of Chris’ favourite spots in the city!
Just south of Vancouver, Canada, you will find Portland, Oregon. The vibrant City of Roses.
Photos by Kevin Butz (@kevin_butz) and Zach Savinar (@zachsavinar)
Portland is home to many diverse and cultured communities, and similar to other cities, it is broken down into distinct neighbourhoods - also known as quadrants. To navigate Portland, it’s important to understand its five quadrant orientation.
On the West end of Portland, you will find the Northwest and Southwest quadrants. This side of the city the most traditional and developed.
Northwest Portland is the shopping district of the city. This quadrant boasts high-end shops and boutiques.
The South West quadrant is where you will find the Downtown core and the cultural center of Portland. This quadrant highlights the city’s Art Museum, as well as public art that is speckled throughout the city.
The east sides of Portland: Northeast, Southeast, and North Portland are known to be more funky, quirky, and electric than the West. You will definitely see something new on this side of town.
Photos by Elena Kuchko (@elena_kuchko) and Zachary Keimig (@zacharykeimig)
Northeast Portland is the largest out of all the five quadrants, and the area Chris calls home. This quadrant is known for its culturally diverse and beautiful neighbourhoods. Chris notes that the best part of this quadrant is its friendliness and strong sense of community.
Southeast Portland is known to be the most electric, and according to Chris, is the place to be. The cool and electric neighbourhood bustling with shops and people in the park makes it the most popular out of all the quadrants.
North Portland is the fifth quadrant of Portland. You would think that there could only be four quadrants, but somehow Portland manages to pull it off. The history behind this fifth quadrant is mysterious, yet very interesting. In the early stages of Portland, what is now known as North Portland was its own city. Portland already had four quadrants, but as it grew, it absorbed the smaller city, adding it to its quadrants.
Transit in Portland
Portland is a small city, and almost everything is in walking distance, especially if you are staying within one quadrant. It is so compact, that Chris says that a ten-minute drive in Portland can feel a long trip to locals.
“A 30-minute drive in Fort Lauderdale is nothing, but a 10-minute drive (in Portland) is the most annoying thing,” says Chris.
Photos by Zachary Keimig (@zacharykeimig) and Elena Kuchko (@elena_kuchko)
If you need to go from quadrant to quadrant, or you are exploring the city for the day, Chris suggests renting a car. The city is small enough for you to see all of the main attractions and neighbourhoods within a day.
If you are going from point A to B, public transit or taking an Uber/Lyft are also great options.
The Portland TriMet provides bus, streetcars, light rail, and commuter rail throughout the city. Load up a hop fast pass, or download the Hop Card app on your phone, and tap once you get onto a bus or train. Adult tickets last for two and a half hours, and go for USD$2.5. Or purchase a day pass for USD$5.
Where to Stay in Portland, Oregon
Portland’s hotels and Airbnbs are a reflection of the city's creativity and spirit.
Photos by The Society Hotel
Chris recommends booking a stay at the Society Hotel, a boutique hotel located in the heart of Portland’s historic neighbourhood, Old Town Chinatown. The Society Hotel offers two types of stays: a traditional hotel room or hostel rooms with bunk beds. Traditional rooms include King/Queen sized beds, and full amenities such as private ensuite bathrooms, robes, and access to the rooftop. Being the only downtown Portland hotel with a hostel-style living experience, this spot is great for social adventure seekers. Each hostel room includes twin-sized bed bunk beds, innovative and secure storage, reading lights, privacy curtains, and access to community spaces, and the rooftop. If you are not convinced, you can get a mix of both experiences with their standard room that boasts a private suite but includes a shared bathroom. Make new lifelong travel buddies, and gain new experiences while at the Society Hotel.
If you are looking for a more traditional hotel stay, check out the Woodlark Hotel, located in downtown Portland. Built-in two historic Buildings, the Woodlark pays homage to Portland’s history and deep-rooted culture. Enjoy locally crafted coffee, access to public bike rentals, fitness classes, at this boutique hotel. Each room’s interior design reflects Portland’s sense of style, art, and culture, and includes a locally inspired mini bar for guests to enjoy.
Photos by The Heathman Hotel
For an upscale stay, book a room at the Heathman Hotel. Having been open since 1927, the Heathman has become an iconic Portland landmark. The hotel reflects the local creative and artistic scene, while seamlessly blending luxury and hospitality for international guests. If you are a book lover, check out their two-story, award-winning, hotel library. The library boasts 2,700 books that have been signed by their authors. Explore modern and historic Portland in this beautifully renovated historic hotel.
If you really want to feel like a Portland local, book a stay at a local Airbnb!
Photos by Airbnb - Nancy
Check out this fully detached guest home located in North Mount Taber. A perfect cozy spot to relax with your significant other. Enjoy the high ceilings, and bright and airy open-concept space, which features an eco-friendly kitchen. Work and play? This spot boasts high-speed WI-FI, so you won’t feel disconnected. Rest after an active day exploring Portland in this cozy Airbnb.
If you are traveling with the whole crew, check out this spacious, two bedrooms and five-bed AirBnB. Located in the Alberta Arts District, you are minutes away from restaurants, bars, and galleries. Have a glass or two with friends, before hitting the town and seeing all that Portland has to offer.
Things to do in Portland
Photos by Sarandy Westfall (@sarandywestfall_photo)
If you feel like a day trip and spending the afternoon by the Pacific Ocean, check out either Cannon Beach or Seaside Beach right along the Oregon Coast. But beware of the colder water up north, or at least pack a warm fuzzy towel and a change of clothing if you take a dip in the ocean.
“You touch the water and your toes freeze,” says Chris, who is much more acquainted with the warm waters of Fort Lauderdale and Jamaica.
Instead of swimming, Chris recommends heading to the coast for a scenic mountain hike. Portland is known for its various hiking trails along the Oregon Coast. Check out the Clatsop Loop Hike for a short but sweet 3-mile hike near Cannon Beach. If it is a misty and wet day, hike up the cliffside for a view that Chris describes as “a scene out of Game of Thrones”.
Photos by Zachary Keimig (@zacharykeimig)
“Picnics are the thing to do during Portland Summers,” says Chris.
Hangout with friends and have a Picnic at one of Portland’s popular parks. Giving Portland’s casual and friendly nature, you will likely make a few new friends as well! Explore Laurelhurst Park and relax under a tree by the pond. The park is 26.81 acres so you will definitely find a suitable picnic spot for you and your social bubble.
Photos by Kevin Butz (@kevin_butz) and Nathan Dumlao (@nate_dumlao)
If you enjoy a cup of coffee in the morning, Portland’s coffee shop scene and coffee culture will blow your mind. There is practically a coffee shop on every street corner. Whether it be to relax and work at a shop, or to coffee shop hop, put Chris’ favourite neighbourhood spot the Albina Press Coffeehouse on your list.
Coffee has you jittery? Why not take a well-deserved break and check out one of Portland’s microbreweries. With 75+ breweries in the city, Portland is home to the most breweries in the world.
Don’t believe us? Take it from a local instead!
Here are some of Chris’ favourite brews from around the city:
Ecliptic, located between Northeast and Downtown Portland is serving up some cold brews with a dash of science. Ecliptic combines brewery owner and craft beer icon, John Harris’ two greatest passions: beer and astronomy. If you are a sour ale type of person, we recommend trying their Tucana Tangerine.
Photos by Widmer Brothers Brewery (@widmerbrothers)
Not too far is Widmer Brothers Brewery, which has become so popular they have opened up a few local chains. Even with opening up other locations, Widmer is consistently pouring great brews. Using only the highest quality of ingredients, we recommend trying one of their wheat beers. Grab a six-pack of Widmer’s year-round Hefe beer to enjoy with a few friends.
Ex Novo Brewing Co has an interesting story with a humble beginning. Circa 2012, Ex Novo began as a garage filled with home brew. Today, the brewery still holds onto its roots and can be described as a “hole in the wall” type place, but has become a Portland staple. With limited seating, you might want to call ahead and secure a spot. Try the light and fresh beer ‘Vienna Waits for You’ while you check out this small bar.
What to see in Portland
Most urban cities have an iconic park, New York City has Central Park, Toronto has High Park, Chicago has Millenium Park, Tokyo has Showa Memorial Park, and so on.
Photos by Anya K. (@anyakarama) and Zachary Keimig (@zacharykeimig)
Portland has Mount Taber Park. While being in the heart of Southeast Portland, Mount Taber Park is the perfect getaway from the bustling city. Nothing short of spectacular, Mount Taber is 196 acres of forests and parklands and sits on top of an extinct volcano cinder cone.
Make sure you wear comfortable walking shoes so that you can see everything Mount Taber has to offer! Play tennis or volleyball in one of the park’s courts, see one or all three of the park’s reservoirs, and picnic in a spot of your choosing or at one of the park’s designated picnic tables.
Insider tip: Chris recommends finishing your day off at the top of the hill to see the sunset over the city. Climb up the stairs, past the reservoir, walk up the hill to see an unbelievable “Google Image” worthy sunset.
If you are feeling like seeing something touristy, scratch that itch at the Oregon Historical Society Museum to see the penny that gave the city its name, The Portland Penny. In 1845, an 1835 American copper penny was tossed and flipped to decide the city’s name. Had it gone the other way, Portland as we know it would be known as Boston, Oregon. For something so small, it has quite the significance and really goes to show Portland’s culture of being carefree.
Best Restaurants in Portland
Built on a creative and diverse crowd, Portland’s food game is not to be messed with. Portland’s creative scene extends far past galleries and street murals, chefs are bringing self-expression and authenticity through the art of food.
Check out these local spots mentioned by Portland resident Chris:
Photos by LECHON (@lechonpdx)
Lechon located along the historic Portland waterfront, and is serving up South American inspired cuisine to the Pacific North West. The entire menu is ‘family style’ to encourage connection with food, flavour, and culture with friends and family. Lechon doesn’t hold back on any details, whether it be the tastes from a dish or pleasurable visuals from the interior design. You won’t be able to take your eyes off the spectacular 1,000-gallon coral reef tank at the entrance of the dining room. Feast your eyes on the jellyfish aquarium behind the bar. Enjoy grilled octopus and fresh ceviche while taking in the scenic views of Lechon.
Photos by Pambiche (@pambiche)
Tucked away in the Northeast quadrant of Portland, you will find Pambiche, a Cuban restaurant serving up traditional fare in a vibrant atmosphere.
“You don’t find too many Cuban restaurants in Portland but when you find one, it’s good,” says Chris.
Start your meal off with an authentic Cuban cocktail before enjoying the bright and spicy flavours of Latin America.
If it’s past 11 PM and you have a hankering for something tasty, check out Chris’ go-to late-night spot: Zien Hong
When a restaurant doesn’t have any social media or even a website, you know it will be good. Zien Hong is serving up large portions of Chinese food at affordable prices all day and all night. This spot is a local favourite for a reason. If you don’t believe us, come and try it for yourself!
Nightlife in Portland
Portland is an interesting place, and due to its relaxed atmosphere and culture, its nightlife scene can be occasionally low-profile. “People will be in bed by 12AM or turn on the fire and read a book,” says Chris.
But if you are looking for a night out, do it like a local and head to Southeast Portland. The Southeast quadrant is a lot more popular and trendy than the typical Downtown scene.
Photos by Quarter World (@quarterworld)
For a Friday night adventure, start your evening off in Mount Taber Park, maybe even catch that sunset we mentioned, then hit up nearby arcade QuarterWorld! Restricted to adults 21+ after 8 PM, enjoy pizza, a full bar, and classic arcade games. Currently closed due to Covid-19, check out this spot for old-school video games when it opens up again.
Photos by Nathan Patrick Wallace( @pandahawk) and Victoria Bar (@victoria_pdx)
Looking for a good cocktail bar to impress your date? Check out Chris’ go-to spot: Victoria Bar. Bask in the intimate and warm setting of this trendy cocktail bar, and enjoy a conversation with someone special. Victoria Bar’s warm interior extends outside to its large covered patio. As daylight dims, hanging fairy lights and tea candles bring sets the mood outdoors.
If you are in the mood for a casual drink, check out Chris’ favourite neighbourhood spot: Free House. Located in Northeast Portland, this bar prides itself on being one of the friendliest bars in the city. Connect with locals and make new friends at this hidden gem.
What to pack for Portland
Ever feel underprepared for a trip? Pack your weekender like a pro by including Chris’ Portland must-haves:
- Bring your laptop. “I’ll jump off a bridge and bring my laptop,” says Chris. Many of Portland’s residents (Chris included), are content creators, and you will see them working at local coffee shops or co-working spaces. You might just be inspired to work on a new project while in creative Portland.
- Extra USB cord and battery pack. Some Portland coffee shops are built in older historic buildings, which can mean no outlets. Packing a USB cord and battery pack will be a savior, especially if you are in a working groove and your laptop suddenly runs out of juice. Nothing is worse than having inspiration strike but not having any device to jot it down - unless you settle with the old fashioned method of paper and pen.
- Light rain jacket. Having a spare rain jacket in the back of your car or bag is essential given Portland’s rainy weather. The weather can also be a bit unpredictable, so it is best to be prepared. Chris advises that you might just experience “all three seasons in one day”. Make sure it is a light and foldable jacket, or you might be caught sweating in the mildly humid and misty Portland air.
- Durable boots. If you are headed to Portland, then you will likely go on a hike or two. Make sure they are something comfortable and water-resistant. If you are packing leather boots, bring a high-quality leather protectant.
- Face wipes. This one might sound odd, but it is Chris’ key to skincare whilst on a hike. If you checked out his Instagram, we are confident that you are already placing a pack or two in your online shopping cart. Don’t be caught slacking on your skincare routine while in Portland’s relaxed atmosphere. “People in Portland don’t groom that much” remarked Chris. Not caring about self-image is great, but make sure you take care of your largest organ, skin! Face wipes are a quick and fast solution to cleaning sweat, mist, or air pollution off your face after a large hike, and prevent unnecessary breakouts. Chris recommends Oars and Alps facial wipes for a quick and on the go cleanse.
- Flannel button-up shirt. You will likely spot numerous flannel shirts being worn across the city. Its versatility makes the flannel shirt popular for a reason. If it’s not raining, wear it out on a hike. If it gets a little dirty, no problem. Just roll up the sleeves and you will look presentable for the day’s activities. Dress like a local, a sport your favourite flannel around the city.
Now that you have the insider scoop on Portland’s bests, its time to start planning your next trip!
And give our buddy and Portland local Christopher Chin a shout next time you are in town.
Check out our latest collection of weekender bags to fuel your inner weekend warrior.
Connect with Chris @septembermondays, check out his digital marketing agency @polishedagency and check out his menswear line @rudemondays.