Portland has an interesting reputation, which I found mostly true. I recently visited Rose City for the first time over New Year’s and witnessed countless beards and flannels, sipped delicious coffee, and ate my way across town. I laughed at some over-the-top hipster elements, such as a bicycle that powered the Vitamix at a smoothie shop, but moreso really appreciated the unique elements that make this city so loved.
There’s plenty to do in the city, especially for outdoorsy types and beer lovers, and cuisine for every taste. I split my time between the East and West sides of town, which I found can be a bit polarizing for locals, and truly got a feel for the town after a week.
I was lucky enough to be hosted by an awesome group of locals (big ups to Robert, Jess, Paul, Molly, Marshall, and the CM House) so this city guide is curated by Oregonians, not random Yelpers. Even after a week in town, I barely scratched the surface of my impressive to-do list so I can’t wait for my next trip out to the Pacific Northwest.
Robert and I crashed at some great Airbnb’s during our stay, which I definitely recommend over a hotel. We had a blast playing house and found that apartment rentals felt more authentic and welcoming compared to a generic hotel room. We shared our time between the Division Street neighborhood on the East Side and right on Hoyt Street in the Northwest. Specifically I recommend Doug’s “Stylish Division St. Hipster Hideout” on Airbnb; it was a true one bedroom in a great location with clean, worldly decor.
If you feel more comfortable in a hotel, there are a few stylish options right in downtown Portland. One night, we all grabbed martinis at the Heathman Hotel, an iconic Portland establishment. It’s classic and old school, and I hate to admit it but I got pretty excited when I realized that it’s continuously referenced in 50 Shades of Grey.
The Ace Hotel is typically a safe bet if you’re looking for something urban and trendy and Portland’s branch is no different. It’s in a great part of town with a funky cocktail and tapas speakeasy (Pepe Le Moko) below the hotel. We stopped in for oysters and a boozy milkshake prior to dinner one evening.
For Your Bucket List
No “to eat” list in Portland skips out on Pok Pok, and with good reason. This iconic Thai restaurant is the recipient of numerous accolades around the world and has expanded into multiple locations including in Los Angeles and New York. We actually crowned Pok Pok’s Brooklyn occasion as our favorite Bloody Mary in 2015’s NYC festival.
Hands down, my favorite item on the menu was the Vietnamese fish sauce wings, served spicy. The sauce was tangy, thick, and zesty while the poultry wasn’t over fried. I ate a ton of fantastic food while in Portland, but those wings were ultimately the top stand out, and coincidentally the first thing I ate while in town.
Portland has a thing for indulgent Southern fare and Screen Door and Pine Street Biscuits topped my brunch lists. There’s so much brunch and so little time so I unfortunately had to table Pine Street Biscuits for another trip. However, we braved the wait at Screen Door and were rewarded with amazing chicken and waffles, biscuit sammies, and praline-crusted bacon. Read our full brunch review of Screen Door here.
For a Sweet Tooth
Every dessert lover must try Salt & Straw when in Portland. The artisanal “farm to cone” ice cream shop (so Portland) features small batch, unique flavor combinations such as strawberry honey balsamic with black pepper, Stumptown coffee & Burnside bourbon, and pear & blue cheese. There are numerous locations across the city and it has now expanded to Los Angeles.
For More Sweets
Voodoo Doughnuts gets all of the credit for iconic Portland-style doughnuts, but skip the touristy destination and have Bitch-approved gourmet bites at Blue Star Donuts. The brioche pastries are made from scratch every day Parisian-style, which includes an 18-hour prep time. Different doughnuts are available each day and sell out quickly. Our favorites du jour were a vegan olive oil cake doughnut and a fresh Meyer lemon curd.
We enjoyed Olympia Provisions for brunch, but this chic butchery is perfect for cozying up with a meat & cheese plate and a big glass of wine anytime of day. The expert staff can guide you through the vast selection of proteins and you can even grab a nice assortment to go. Read our full brunch review of Olympia Provisions here.
For a Sceney Dinner
To see and be seen, go no further than downtown Portland. Trendy 20 and 30-somethings flock to Departure, Imperial, and Tasty n Alder for upscale food and bespoke cocktails. I personally wanted a more rustic, “Portlandia” experience, but these locales are chic and reminiscent of Manhattan.
For Date Night
Besides Sugarfish in LA, Bamboo Sushi is some of the best I’ve had in the United States. The restaurant only uses certified sustainable seafood, but manages to keep the prices relatively reasonable. Try the salmon flight for five slabs of locally caught, melt-in-your-mouth fishy goodness. It’s unlike anything I’ve ever tasted! The vibe is also quiet and romantic, perfect for date night.
After a beer-fueled evening cheering on the Trailblazers, we were craving some greasy food to cap off the night. We stopped into TILT in the Pearl District, a burger and craft beer spot, which was quite a scene at night. There are more than 20 different types of burgers, sandwiches, and biscuits (again with the biscuits!) so there’s sure to be something to please everyone in your party. The restaurant is pretty sizable too so we appreciated that there was no wait despite the popularity of the joint.
Portland’s coffee deserves its own post, it’s really that good. I primarily stuck to Stumptown Coffee Roasters (numerous locations) and Coava Coffee brewed at Barista, a stone’s throw from our accommodations in the Northwest neighborhood. Pretty much every coffee shop you step into will have a unique ambiance, a great playlist, and non-dairy milk alternatives, which is a huge plus in my eyes.
For Book Worms
Get lost with a good book at Powell’s City of Books. The iconic, massive bookstore has been a Portland establishment since the 70’s and claims to be the world’s largest independent book store. After you settle on a good read, grab a cup of joe from nearby cozy venue, Courier Coffee.
Recreational marijuana use is legal in Oregon and dispensaries have popped up all over town. Regardless if you hit the pipe, perusing the local selection and picking the minds of staff members at the dispensaries is fascinating. I was pleased to find that the dispensaries were clean, well organized, and generally not shady. Check out Rip City Remedies, which is conveniently located next to Salt & Straw’s Division Street location, if you catch my drift.
For Design Aficionados
There are a number of chic, rustic home decor shops scattered around the city. Pick up a unique local piece as the perfect memento from your trip. Notable boutiques include Ink & Peat, Canoe, and Alder & Co.
For Fit Bitches
There’s plenty of outdoor activities to keep you busy–and sweating–during your time in Portland. Before it got too icy, Robert and I laced up our sneakers (Nike of course) and went on a few beautiful runs. We particularly enjoyed the Waterfront Loop and Mount Tabor Park.
Although it’s a bit touristy, we headed up to Pittock Mansion, a 20th century château nestled in the hills with a killer view of the entire cityscape. We took a quick Uber up to the site and then leisurely strolled back down to the Northwest neighborhood, which took about 30 minutes. You’ll see some gorgeous homes with interesting architecture during your descent.
For Snow Bunnies
Although it rarely snows in Portland, there’s plenty of powder in the nearby mountains. If you head towards Mount Hood and Lake Trillium, there are numerous mom-and-pop rental shops for outdoor activities such as cross-country skiing and sledding. We tried snowshoeing for the first time and had a blast. We were treated to gorgeous views and a great cardio sesh, and the snowshoes were very easy to navigate. Just be sure to head towards the mountain early; it gets crowded later in the afternoon.
For Sports Lovers
Join Blazer Nation and head to the Moda Center to see Portland’s professional basketball team, the Trailblazers, in action. Prior to the game, grab some drinks at Spirit of 77, a fun sports bar nearby with craft beer, bar games, and plenty of big screen TVs.
For Your Instagram
For cheap (and quick) thrills, take a ride on the Portland Aerial Tram. The ride only takes four minutes each way and costs less than $5 roundtrip. It’s a beautiful way to experience a bird’s eye view of the city and put everything into perspective.
Portland Bitch Tip: If you are a women’s shoes size 9 or smaller, you can fit into Nike Youth sizes. I’m an 8 women’s and fit into a 6.5Y. Shop in the kids’ section for cheaper kicks and a more unique selection.