The insider’s guide on where to party, stay, shop, and eat in Portland

Daniel Villarreal, a Senior Editor at LGBTQ Nation, GayCities‘ sibling news site, moved to Portland in 2018 for the natural beauty, vibrant queer community, and to move in with a silver daddy he was long-distance dating. Their relationship quickly fell apart, but Daniel has stayed in love with the city, its accessible hikes, and its relaxed pace of life.

He now lives in the city’s “northern quadrant,” just a short drive from its renowned restaurants, shopping districts, tourist hotspots, and the natural wonders of Columbia Gorge.

GayCities chatted with Daniel to get his insider take on everything from the best bars to the tastiest spots in Portland. Let’s dive into their recommendations below.

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GAYCITIES: When you go out with your friends in Portland, where do you bar-hop, and in what order?

DANIEL: Portland is a wonderland of both high-end cocktail lounges and excellent scuzzy bars. Usually, I’ll do an early drink at Hele Pale, a charming tiki lounge with delicious fruity drinks and “tropical storms” with lighting and thunder every hour. (Show up early, though, as the bar fills up quickly.) Sometimes, I’ll take them to McMenamins’ Back Bar behind the Bagdad Theatre because of its mind-blowing high ceilings and murals.

After that, I always enjoy grabbing a happy hour at Scandal’s because it has heavy pours, friendly locals, outdoor seating, and decent people-watching. Then, depending on the mood, I’ll either take pals to The Eagle if they want a sexy vibe, Back 2 Earth if they want a good DJ spinning over a nice chat, or The Florida Room if they want a scuzzier and queer dive-bar atmosphere.

Plus, state law requires all bars to serve food, so you can always grab a bite at any place once you get hungry. Also, I gotta say, while it’s not a gay bar, Dante’s in downtown Portland has a fabulous Sunday night Sinferno Cabaret filled with male and female gogo dancers, flow artists, and pyrotechnics — it’s worth it if you don’t mind staying up late before the work week starts.

Which gay bar is your favorite?

While I’m definitely an Eagle guy because of its sexy vibe, the out-of-towners all want to go to Silverado and Stag PDX because they’re known as the must-visit strip clubs. Still, if you’re actually looking to make out or go home with a fella, the Eagle is where it’s at.

I also love Workers Tap & Cafe. It’s a quiet, unassuming coffee house and bar, but it’s known locally as a socialist bar because it’s worker-owned and operated. It’s also a popular hangout for trans locals and allies, so it can be a great place for a spirited conversation or blowing off some steam when the world’s getting to ya.

For queer women, Doc Marie’s is a solid bet. It’s stylish AF, has regular theme nights and weekly queercore, and makes everyone feel welcome.

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Who is the best drag queen in the city?

Oh geez, there are so many great ones. Bolivia Carmichaels and Poison Waters are two definite standouts. They circulate amongst various drag venues like CC Slaughters (which tends to pull in a younger crowd) and Darcelle XV (which tends to skew older), but they’ve also done a lot of great local, political activist work, too. This matters deeply to me and many others in a city known for its progressivism.

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Which hotel do you suggest for out-of-town friends?

Most of my visitors are bohemian queer artist types and typically looking for inexpensive digs. On the no-frills end, The Society Hotel in Chinatown is super affordable. Some of its rooms were recently redesigned by Asian-American artists, its lobby is a coffee bar where you can work or chill, it has a rooftop bar, and is close to several gay bars. Hotel Zags is more upscale but still affordable — the entire place was recently revamped in stylish comfort. I also really like The Crystal Hotel. Its rooms are cozy and charming, and it has a great restaurant and an underground soaking pool open to overnight guests.

What is your favorite food, and where do you get it in Portland?

Being from Texas, I made it my mission to find good Mexican food. The best I’ve found is a food cart called Quesabrosa. It has a surprisingly robust menu, and its street tacos and burritos are deliciously filling. They have really reasonable prices to boot. I also love Asian food, though, so for Thai, I hit up Sweet Basil near the Hollywood district, or for Chinese-American, I go to Duck House downtown — both offer large family-style portions perfect for sharing or taking home and enjoying later.

Also, if you want a killer dessert, nothing beats Papa Heydn. It has two posh locations and a diverse dessert offering that makes a great date or birthday treat that won’t break the bank. And while all the out-of-towners queue up outside of Voodoo Donuts, skip it. Get an amazing gourmet donut instead at Blue Star Donuts; they’ve got four locations around the city and even one in the airport, in case you want to pick up a sweet treat or culinary gift before you leave.

Where do you like to go shopping in Portland?

I direct first-timers to the Saturday Market because you can always find small trinkets, artworks, and other treasures that make good gifts or keepsakes. Powell’s Bookstore downtown is also a trustworthy place to get quirky Portland-themed souvenirs like mugs, journals, socks, tote bags, and plushies.

The other thing most people don’t know about Portland is that many neighborhoods have their own small corridors featuring a walkable array of clothing boutiques, bars, food cart pods, and eateries. The ones on Alberta Street and Hawthorne Boulevard are perfect for their length and variety, perfect for an evening or afternoon stroll.

Being a gaymer geek, I always direct video game nerds to Hawthorne Game Exchange and TOTL Games, both trans-owned and operated by two kind and knowledgeable owners. To satisfy my witchy inclinations, I always enjoy The Raven’s Wing, Moonshadow, and Celestial Awakenings — they all have great collections of books, pendants, charms, stones, tarot cards, and other must-have accouterments.

What’s the best part about the nightlife in Portland?

I gotta be honest: Portland’s nightlife died after COVID-19. You can still find dancing and late-night fun if you look around, but even most of the restaurants close around 9 p.m. We have many great local taprooms that feature a mind-bending number of tasty local brews, but if you’re coming here for the nightlife, don’t.

Portland is all about the outdoors. The weather is amazing from May to October, but from November to April, it’s colder and often drizzling. The nonstop grey weather during that time depresses some locals, but it doesn’t stop the more adventurous ones from getting out with a rain slicker and hiking boots.

I always take out-of-town friends to the International Rose Test gardens during the sunnier months. Parking there can be tough (especially on weekends), but on weekday evenings, it’s less crowded and a perfect place to see some eye-popping rose varieties you’ve never seen before. It also has a nice amphitheater that is great for sitting and chatting, and the Japanese Gardens are located just across the street. (The garden is pretty small but still impressive, and it has a good gift shop.)

I always take gay adventure seekers and sun worshippers to Rooster Rock State Park. It’s the only state park in the U.S. (as far as I know) that has a clothing-optional beach and a cruising area. It’s flooded for part of the year, so you’ll want to check the water level online before going. It’s also about a 20-minute walk from the parking lot, so pack and choose footwear accordingly. But the river there is calm and cool, and it gets pretty lively on weekends. The sunsets there are amazing, too.

For older or less mobile visitors, I take them driving along the Historic Columbia River Highway. It crosses a handful of small local waterfalls that you can get out of the car and take pictures next to. It also passes Vista House at Crown Point, which offers breathtaking views of the river gorge, a stylish building, and a small gift shop filled with all sorts of small delights.

The city is also filled with great parks where you can discretely enjoy a drink, stony stroll, or take your dog for a leash walk. Most people like Mount Tabor or Laurelhurst, which have nice views, lawns, and long walking paths. But I prefer two northern parks: Alberta Park (which has a pavilion, a playground, a rare plants garden, a dog run, and large grassy fields) and Peninsula Park, which is like a mini-version of the International Rose Test Garden with a large fountain, small playground, grassy field, and a community pool.

But there’s also a secret gem of a park in the north quadrant that’s easy to miss and hardly anyone ever goes to: Cully Park. It’s a newly designed 25-acre park with modern play structures for kids, pavilions and seating for picnics, a native plant garden, a circuitous workout path, and a fenced-in dog area. It’s located close to the airport, so you can see planes taking off and landing at all hours, which is cool.

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