The Hipster’s Guide To Portland

Over the last decade, something has been drawing large numbers of millennials to America’s weirdest city. In fact, in just the last couple of years, more than 10 of my friends have moved there! It could be because of the affordable rent, the lush green forestry, or all the fun and unique things to do there. 

I hadn’t been to Oregon since I was a kid, and since I now know so many locals, it seemed like as good a time as any to see for myself what all the hype was about. I spent a few weeks getting to know the city pretty well, and I wanted to share all my discoveries and experiences with you! I’ve named it “The Hipster’s Guide To Portland”, because, let’s face it, I’m a major hipster and I strive to find all the lesser-known offbeat attractions. This is the first in an ongoing series “Hipster’s Guides”, each filled with non-touristy things to do, helpful information, and honest recommendations. So, here goes!

KNOW BEFORE YOU GO

When to go: Fall and Spring are the best times to visit a city like Portland. In the summer it gets humid and crowded, and in the winter, you risk the dreaded snow day (everything in Portland comes to a halt when it snows). In the Spring and Fall, the trees are beautiful, the weather is pretty mild, and there aren’t an overwhelming amount of tourists. Fall is my favorite season and Portland is the perfect place to spend it, so I recommend visiting in late October – early November. 

Get an early start: The only downside about visiting in the fall is that the sun sets early, usually around 4:30 pm. Even if you’re visiting during another time of year, a lot of businesses close by 6 pm, so if you’re planning on doing a lot on your trip, you’ll have to be cool with starting early in the day.

Getting around: If you plan on driving while you’re visiting, it’s important to be aware that it’s illegal to pump your own gas in Oregon. I know, it’s super weird. Just pull up to a pump and someone will be there to help you out. As for parking, while you’re in the city, you’ll have to pay in most areas. The good news is that there’s a really awesome app you can download on your phone called Parking Kitty, which will allow you to pay for parking, see how much time you have left, and even add more time without having to return to your car.

You’ll need cash:  A lot of local businesses are cash only, and a lot of the ones that take card will only accept debit. Just to be safe, keep cash on you while you’re in town. Oh, and enjoy going shopping without having to pay sales tax!

What to wear: In Portland, you’ll want to dress warmly, but wear layers in case it starts getting toasty. I recommend starting with a good coat, a cardigan/sweater, a scarf, some long sleeve shirts, and some good weatherproof walking shoes. Here are some of my favorites:

CAN'T-MISS EXPERIENCES

Grab coffee from a friendly barista: There’s a good chance you’ve heard of Dutch Brothers, but if you’ve never picked up a cup of coffee from one of their drive-thru’s, it’s the perfect way to start a long day of sight-seeing! Their baristas are known for being extremely friendly, and their coffee is pretty damn good. And if that isn’t exciting enough for you, Portland also has a bunch of drive-thru coffee stands featuring “bikini baristas.” Needless to say, that’s not really my thing 😂 but hey, live and let live. 

See the city on a bike: Traffic in Portland is surprisingly awful, especially during the tourist seasons. Navigating around the city could be a nightmare if you don’t love the idea of spending hours on foot or wasting time and money sitting in traffic. Hopping on a bike is a popular alternative amongst both visitors and locals!

Go on an adult scavenger hunt: McMenamins is the world’s coolest chain of bars (and hotels, venues, restaurants, spas, and theaters). All throughout the Pacific Northwest, they’ve repurposed historic buildings, bringing new life to them. I highly recommend taking advantage of their passport system so you can collect stamps at every location and other miscellaneous rewards along the way!

Grab coffee from a friendly barista: There’s a good chance you’ve heard of Dutch Brothers, but if you’ve never picked up a cup of coffee from one of their drive-thru’s, it’s the perfect way to start a long day of sight-seeing! Their baristas are known for being extremely friendly, and their coffee is pretty damn good. And if that isn’t exciting enough for you, Portland also has a bunch of drive-thru coffee stands featuring “bikini baristas.” Needless to say, that’s not really my thing 😂 but hey, live and let live. 

See the city on a bike: Traffic in Portland is surprisingly awful, especially during the tourist seasons. Navigating around the city could be a nightmare if you don’t love the idea of spending hours on foot or wasting time and money sitting in traffic. Hopping on a bike is a popular alternative amongst both visitors and locals!

Go on an adult scavenger hunt: McMenamins is the world’s coolest chain of bars (and hotels, venues, restaurants, spas, and theaters). All throughout the Pacific Northwest, they’ve repurposed historic buildings, bringing new life to them. I highly recommend taking advantage of their passport system so you can collect stamps at every location and other miscellaneous rewards along the way!

WHERE TO STAY

McMenamins Kennedy School

5736 NE 33rd St. Portland, OR 97211

The John D. Kennedy Elementary School, which was built in 1915, is one of the historic buildings McMenamins has taken under its wing. The bedrooms are all cozily furnished, some of which even include original chalkboards so you can enjoy “falling asleep in class” in the most authentic way possible! In addition to being a hotel, the building also houses a restaurant and several bars, each with their own theme and character, and a movie theater! Whether you’re just stopping by for a quick drink or booking a room for the duration of your trip, this is one of Portland’s most unique spots, and I highly recommend adding it to your itinerary.

Ace Hotel

1022 SW Stark St. Portland, OR 972005

The Ace Hotel is a gem in the heart of downtown Portland. This hotel features beautiful minimalistic decor, rooms designed with comfort in mind, and a location that’s as prime as it gets! And to make your stay as enjoyable as possible, they allow pets, and they have bikes available to rent so you don’t have to navigate the city streets on foot (everyone rides bikes in Portland, so you’ll fit right in). The building dates back to 1912, and the Ace has done a fantastic job of offering all the modern amenities you would expect in a brand new hotel, all while maintaining the charm and history. The building is also home to a really good restaurant and bar, Clyde Common, as well as a Stumptown Coffee. If you’re looking for the perfect combination of comfort and convenience, this is the place!

EAT & DRINK

A Belgian waffle with fresh fruit and a mimosa flight at Marcos Cafe in Portland, Oregon
Belgian Waffle from Marco's Cafe

The Essentials

Burgerville: Typically, I’m not much of a burger person, but I love me some Burgerville! This chain exists exclusively in the Pacific Northwest, so when I’m in the area, I have to make a trip to one of their locations. They have an option to build-your-own burger, and their topping selection is unmatched! 

Salt & Straw: The weirdest ice cream shop you’ll ever visit. Their classic menu includes flavors such as pear & blue cheese, strawberry honey balsamic & black pepper, and Arbequina olive oil. But, their rotating seasonal flavors are the main attraction! When I visited in November I tried their salted caramel thanksgiving turkey flavor, and it is literally my favorite ice cream ever. The weirder they sound, the better they taste! 

Poplandia: Here you’ll find some really good gourmet popcorn featuring unique rotating flavors, both savory and sweet! You can get fresh popcorn to snack on while exploring, or pre-packaged bags for later. Don’t be shy about asking for samples!

Voodoo Donuts: I usually wouldn’t recommend something as popular as Voodoo Donuts, but if you’ve never been, you just have to go because their donuts are so weird. They’re open 24/7, so try to go at night if you want to avoid standing in line for 30 minutes. It’s also cash only, but they have an ATM.

My Favorite Restaurants

Cypress Room

5736 NE 33rd Ave, Portland, OR 97211

This is my very favorite place to grab dinner! The food is incredible and the ambiance is so cozy, but what I love most is that it’s located inside Mcmenamins Kennedy School.  You can grab dinner here, sample some of their craft brews (I strongly recommend the Ruby ale), check out a movie at the theater, and you can even go bar hopping within the building! I also really encourage you to check out some of the other McMenamins locations around the city, such as the Chapel Pub, the Crystal Ballroom, and Ringler’s Annex. If you’re interested in visiting several McMenamins, they offer a passport system so you can collect stamps at every location and other miscellaneous rewards along the way. 

Cheese & Crack Snack Shop

One of the charcuterie boards at Cheese and Crack Snack Shop in Portland, Oregon

22 SE 28th Ave, Portland, OR 97214

Have you ever had brie brûlée? Neither had I until I had a cheese plate here, and I am forever changed. Their menu includes an array of charcuterie boards, great for sharing or enjoying by yourself (trust me, you’ll want to eat all of it). If you’re in the mood for some light snacking, this is the very best place! 

Marco’s Cafe

umbrellas hanging from the ceiling at Marco's Cafe in Portland, Oregon

7910 Southwest 35th Drive, Portland, OR 97219

Marco’s is the perfect spot for a brunch date. They have delicious food, quirky decor, and a mimosa flight that is simply heaven. I came here with a couple foodie friends of mine, and we were all thrilled with what we ordered! I ordered the Belgian waffle, and it was to die for. The only downside is that there’s usually a wait if you don’t make reservations, but that’s how you know it’s good!

My Favorite Bars

Bartini

Three different martinis and a pot of fondue with bread for dipping at Bartini

2108 NW Glisan St. Portland, OR 97210

Happy Hour: 4pm-6:30pm, 9:30pm-close (drinks are only $4.50!)

My favorite bar in Portland! As if the fact that their menu includes over 100 different martinis wasn’t enough of a reason to pay Bartini a visit, they also have a whole host of delicious food, as well as beer and wine. If you’re not much of a bar fly, Bartini is attached to a restaurant, Urban Fondue, and you can order drinks off Bartini’s menu while enjoying a more traditional dining experience. I should also disclose the fact that they have the best fondue I’ve ever had (my favorite is the Oregon Black Truffle), and you can’t really go wrong with anything on their menu. 

Secret Society

116 NE Russell St. Portland, OR 97212

Happy Hour: 5pm-7pm Sun-Thurs

Van Gogh, Oscar Wilde, Ernest Hemingway, Édouard Manet… What do all these people have in common? Well, in addition to being incredibly gifted creatives, they all “danced with the green fairy”, if you catch my drift. In other words, they were all absinthe drinkers. Because it was believed to turn drinkers into murderous psychopaths, absinthe was banned in the United States in 1912, and its prohibition wasn’t lifted until 2007! A lot of people are still wary of the fairy, even though it has been proven to be no more harmful than other spirits, so you can’t find it in just any bar. Secret Society is one of the few bars that offer an authentic absinthe-drinking experience. I don’t want to spoil it for you, but if you like black licorice, you’re in for a treat. 

THINGS TO DO

Pittock Mansion

3229 NW Pittock Dr, Portland, OR 97210

Admission: $12 for adults, $11 for seniors, $9 for children 6-18, free for children under 6.

The Pittocks were one of the wealthy families who helped found Portland, and if you pay attention, you’ll see their name all around the city. Most notably, though, at the home they built, which is now open to the public. The Pittock Mansion was completed in 1914, and, like most Edwardian and Victorian mansions, it’s said to be haunted. Don’t fret, though; the ghosts are rumored to be friendly! So whether you’re interested in the paranormal, architecture, history, or culture, this is one of the attractions I most highly recommend!

Movie Madness

Some of the many authentic Hollywood costumes featured in the museum

4320 SE Belmont St, Portland, OR 97215

Remember the good ol’ days when you’d have to go stand in line at Blockbuster if there was a certain movie you wanted to watch? Movie Madness is a huge video rental store that’s helping keep the dream of the 90’s alive in Portland! While you’re searching their huge collection for your favorite film, you may notice that the walls are covered in movie memorabilia; the knife from Psycho, the baby carriage from the Untouchables, Tony Curtis’ hat from Some Like It Hot, and so much more! Yes, Movie Madness is also home to the Museum of Motion Picture History, which is a must-see for all film buffs!

The best things in life are free, and so is this handy guide I made you! These five quick tips will help you take better travel photos, even if your only camera is your phone! 

House of Vintage

A shot of the front window of the thrift shop, House of Vintage, in Portland, Oregon

3315 SE Hawthorne Blvd, Portland, OR 97214

If you’re hoping to do some thrifting while you’re in Portland, this is the place. Don’t let the photo fool you; it’s a huge store! They have rooms upon rooms of authentic vintage clothes, all at great prices. And if that’s not enough for you, there are several other great vintage shops all within walking distance.

Paxton Gate

4204 N Mississippi Ave, Portland, OR 97217

This delightful curiosity shop is a biologist’s dream come true! I felt like I was walking into Charles Darwin’s study. Here you can browse (and shop) their vast collection of taxidermy, exotic plants, mounted insects, jewelry, gems and crystals, and works made by local artists. What I love about this place is the fact that they make learning about natural sciences fun and interactive! They regularly host all kinds of events, including workshops for children, animal encounters, art openings, and preservation classes. They’re very involved in the community and all their employees are incredibly knowledgable and friendly!

Freakybrutte Peculiarium

Address: 2234 NW Thurman St. Portland, OR 97210

Admission: $5

Have you ever wanted to know how it would feel to be buried alive? Would you like to venture inside the brain of a zombie? Have you always dreamt of being the victim of an alien autopsy? If you said “yes” to any of these questions, I like you. But also, you can experience all these things and so much more at this very strange museum, which is unlike anything else you will ever see. 

Smith Teamaker

A tea flight with four unique teas from Smith Teamaker

1626 NW Thurman St, Portland, OR 97209

At Smith Teamaker, all the teas are prepared with love and care. The servers will gladly give you a very thorough background as to how and why each tea was perfected, what parts of the world the flavors were inspired by, and how each tea was created as thoughtfully and deliberately as a work of art. Their menu includes dozens of unique tea blends, and you can even have them prepare a tea flight so you can choose and try up to four different brews.

Powell’s City of Books

Bookshelves inside Powell's City of Books in Portland, Oregon

Address: 1005 W Burnside St. Portland, OR, 97209

The rare book room closes at 7pm.

Even though Powell’s is a popular tourist destination, it’s still a must-see for any book lover. The store takes up an entire city block and has several floors. I spent about five hours here (not an exaggeration) and still didn’t see everything. If you’re hoping to do some quiet roaming through the hundreds of aisles of books, it’s much less crowded at night than it is during the day. If you’re still too overwhelmed at the thought of visiting, there’s another smaller location on Hawthorne that isn’t nearly as busy. 

Lone Fir Cemetery

Address: SE 26th Ave. & Stark St. Portland, OR 97214

Most people never think to visit cemeteries when they’re planning a trip, but when I travel, my mission is always the same: find the coolest cemetery, and take a stroll (preferably at dusk)! Lone Fir is the oldest (and quite possibly the most beautiful) cemetery in Portland, and it was even recognized by National Geographic as one of the top 10 cemeteries to visit in the world! 

Rimsky-Korsakoffee House

A dummy sitting in a kayak in an ocean themed bathroom

Address: 707 SE 12th Ave. Portland, OR 97214

Cash Only

This place is the epitome of Portland. It’s a coffee shop located in a repurposed house, where you can sip your coffee or tea surrounded by their quirky baristas, and very weird decor (especially in the bathroom). I honestly don’t think the essence can be captured with mere words; you just have to experience it for yourself!

QUICK SIGHTS TO SEE

Ace Hotel Photo Booth: The photo booth in the lobby of the Ace Hotel is an antique in its own right. It’s the only photo booth I’ve ever been in that still uses darkroom technology, which, as a photographer, I appreciate more than most people might. The photos take a little longer to develop than with digital photo booths, and they come out smelling a bit like sulfur, but it’s really fun and totally worth it. 

Mill Ends Park: Behold the world’s smallest park in all of its glory! Leslie Knope would be so proud! During major holidays like Christmas and Saint Patrick’s Day, people decorate this adorable local landmark, so it’s fun to visit during different times of the year! 

Dante’s: The “Keep Portland Weird” sign is one of the most iconic selfie spots in the city. It’s located in the back parking lot of Dante’s music venue. I haven’t gone to Dante’s for the live music, but it seems like a cool place to catch a show, and since Portland has an excellent music scene, you may want to venture inside!

St. Johns Bridge: Downtown Portland has lots of bridges. Everywhere you look. But the most aesthetically pleasing is the St. Johns Bridge. Take a quick drive across or admire it from afar!

Ace Hotel Photo Booth: The photo booth in the lobby of the Ace Hotel is an antique in its own right. It’s the only photo booth I’ve ever been in that still uses darkroom technology, which, as a photographer, I appreciate more than most people might. The photos take a little longer to develop than with digital photo booths, and they come out smelling a bit like sulfur, but it’s really fun and totally worth it. 

Mill Ends Park: Behold the world’s smallest park in all of its glory! Leslie Knope would be so proud! During major holidays like Christmas and Saint Patrick’s Day, people decorate this adorable local landmark, so it’s fun to visit during different times of the year! 

Dante’s: The “Keep Portland Weird” sign is one of the most iconic selfie spots in the city. It’s located in the back parking lot of Dante’s music venue. I haven’t gone to Dante’s for the live music, but it seems like a cool place to catch a show, and since Portland has an excellent music scene, you may want to venture inside!

St. Johns Bridge: Downtown Portland has lots of bridges. Everywhere you look. But the most aesthetically pleasing is the St. Johns Bridge. Take a quick drive across or admire it from afar!

COOLEST NEIGHBORHOODS

COOLEST NEIGHBORHOODS

Alphabet District

Portland’s Alphabet district is my favorite neighborhood. The name comes from the way the street names are all in alphabetical order (Davis Street, Everett Street, Flanders Street, etc). It’s the perfect area to go for a walk, and there are tons of restaurants, shops, and bars to explore. 

Pearl District

One of my local friends described the Pearl district as the “bougie” part of downtown Portland. It was once an abandoned industrial area, but in recent years it’s been transformed into one of the city’s most vibrant and artsy neighborhoods. Here you’ll find upscale restaurants, boutiques & shops, art galleries, coffee shops, etc. This is a must-see if it’s your first time in Portland!

Hawthorne District

This is another really great neighborhood that truly reflects Portland’s quirkiness. The streets are lined with indie theaters, music clubs, pubs, bookshops, vintage shops, gluten free/ vegetarian/ vegan eateries, and even an extinct volcano! 

DAY TRIPS TO TAKE

Timberline Lodge

The facade of the Timberline Lodge in Oregon

The Timberline Lodge sits right at the foot of Mount Hood, about an hour and a half east of Portland. It may look familiar, as it was used as the exterior for the Overlook Hotel in the Shining! There’s a little free museum in the lobby that commemorates the hotel’s involvement in the Shining, and, if you ask nicely, there’s even an axe that you can pose with. But, unlike the Overlook, the Timberline is also a ski lodge, so if you’re into outdoor sports, it’s a great little weekend getaway. 

Salem

Oregon’s capital city is just an hour’s drive from Portland, so it’s totally worth taking a day or two to get to know Salem. It’s very quaint for a capital city, but there are some really cool attractions and it’s a great place to visit if you’re looking for a slow-paced vacation.

Seattle

Seattle is one of my favorite cities in the world. You could easily spend a week or two here and still not see everything, but if you don’t have that kind of time, a day or two is still enough time to see the essentials.

THINGS THAT DIDN'T MAKE THE LIST

International Rose Test Garden

A beautiful rose garden with over 600 varieties of roses.

Best of British

Another great tea shop, featuring traditional British treats (and accents)! The location is a bit weird, though.

Paymaster

A fun bar in the Pearl district that features fun arcade games, indoor and outdoor seating, pool tables, a photo booth, and some delicious food and drinks.

Stepping Stone Cafe

A really quirky little diner in the alphabet district with great food and a fun atmosphere. 

Multnomah Falls

A beautiful (but very touristy) waterfall about an hour’s drive from the city.

So, there you have it! I hope this guide will help you plan the perfect trip so you can have the best Portland experience possible! Did I leave anything out? What information should I include in my next city guide? Let me know in the comments! 

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