Girlfriends’ Guide To Portland

Funky bars, PNW road trips, Twilight-esque hikes, lots of laughs & even more moss.

If you’re trying to plan a trip with your girlfriend(s) and can’t decide where: 10/10 recommend choosing a show/event in a city you haven’t been to & making a weekend out of it.

Katie & I sporadically bought Girls Gotta Eat live show tickets last fall after they announced the 2022 lineup. Were they coming to Kansas City, where Katie lives? Yep. Did they do a show in Denver? Also yes. But naturally we wanted to fully optimize the experience by traveling somewhere new. We’d both never been to Portland or Seattle, and Portland flights were cheaper, so there you have it.

I feel very strongly that we actually nailed our itinerary in how we balanced city activities vs. outdoorsy things / exploring outside the city, so I really would recommend planning your weekend similarly if experiencing both aspects is a priority for you. My only regret is that we had more days - we barely even scratched the surface of my list of bars stemming from “weirdest bars in Portland” research.

We stayed in an Airbnb studio in the Humboldt neighborhood, about 20 minutes from the airport and 10 minutes north of downtown. We decided to go the Airbnb route because it panned out to be cheaper than most of the boutique hotels I was comparing with. It was a perfect size and a central enough location to get around easily—on trips like this I think location + price are the most important factors, because it’s really only serving as a home base for all other experiences. We drank some homemade mezcal mango margs & hung out here before the show on Thursday, otherwise we were pretty much only there to quickly regroup before bopping away to a different activity and to sleep (although if anyone knows me or Katie - we barely did that either).

Being 10 minutes from downtown made Ubers super cheap, although when we were there at the end of March 2022, there was a pretty significant Uber/Lyft shortage - waiting 10+ minutes for a ride was common, something I haven’t experienced in Denver in quite a while. One driver mentioned this was because gas prices are so high right now - making ubering less profitable for drivers. Despite high gas prices, Katie & I decide to rent a car. We used the Turo app, which I cannot recommend enough. Katie got this idea from her friend about a week before our trip and it was truly a game-changer. The app & communication with the car owner was frictionless, our red Nissan Rogue, aka Big Red, was a trooper, and it was super affordable compared to the traditional car rental route - $160 for 2 days, $80 per person. This included insurance coverage that was half that total ($40/person).

TOP 3 REC'S:

Should-do Travel Hack: Rent a car

Must-do activity: Multnomah Falls

Must-visit bar: Multnomah Whiskey Library

THE SHORT VERSION ITINERARY:

• Thursday night - seeing a show, going out, drinking a lil too much

• Friday - exploring the surrounding PNW in our car, Multnomah Falls hike, Government Camp road tip, dinner/drinks downtown

• Saturday - “cityscape excursion day” - hiking in Forest Park, Japanese Gardens, daytime downtown bopping, dinner/drinks in north Portland

THE LONG VERSION ITINERARY:

Color coded, obviously.

Coffee shop | Activity/attraction | Restaurant/pub | Dive bar | Cocktail bar

THURSDAY - NIGHT ON THE TOWN

• Red-e Coffee: 5/10. I landed around 9am and planned on working remote for the day before Katie arrived at 4ish. I Ubered to a different coffee shop nearby first, but was told by the bearded & jaded barista that they weren't open for indoor dining. So I lugged my suitcase down the street a few blocks to this lil spot. I got a tea because I'd already drank a shit ton of coffee (I don't like tea) and a satisfactory banana nut muffin. The vibes were not ideal for working or also for feeling joy - it was so quiet you could hear a pin drop.

• McMenamins Chapel Pub: 9/10. Due to the alarming lack of background noise in this^ coffee shop, I packed up my things and walked another few blocks to this quirky restaurant/bar set in an early 1900's chapel. We LOVE repurposed churches. The noise level here was much more appropriate for the unfortunate few meetings I had left, and the server was equally unamused as he was accommodating in letting me post up in the unoccupied private events room. I ate my tuna sandwich & tater tots (bomb) and finished my work day with a stain-glass window backdrop - can't complain about that.

• Rogue Brewery: 8/10. We chose this spot for a late dinner solely because it was in walking distance of the show venue and still serving food, but it was great anyway. Katie got a turkey club, I got a veggie sandwich & we drank canned espresso martinis?! The espresso martini movement is truly unmatched.

• Revolution Hall: 7/10 for the venue, 10/10 for the show. I saw pictures of this venue when we bought the tickets and thought it looked like a high school auditorium - aka not the coolest looking venue on the block. Funnily enough! It did indeed used to be a high school. Which actually kind of makes me appreciate it more. The 1900's building has character and the auditorium does feel very retro. Not a bad spot to see a show in Portland!

• Roadside Attraction: 9/10. This was the first bar we were able to check off my Coolest Bars in Portland list. It was in walking distance of Revolution Hall and the perfect place for a nightcap. This dive bar reminds me of The Hawk on the outside (IYKYK), with the addition of a secret garden-like patio & fire pit, and the inside is kooky, artsy, full of weird as f*ck decor and cash only. Felt very time & place for ending our first night with Keep Portland Weird vibes.

FRIDAY - PNW MINI ROAD TRIP DAY

• Kanios Coffee: 8/10. We stopped here for breakfast after picking up Big Red. This lil hole in the wall is in an unassuming building off a kinda busy street, but the inside is adorable and the coffee/food was top notch. We got iced oat milk lattes with bourbon maple syrup (YUM), Katie got a bacon egg & cheese breakfast sammie and I tried a smoked trout situation on an everything bagel. Perfect cure to suppress a late onset hangover and ideal way to start our adventure day.

• Multnomah Waterfalls: 10/10. We cruised in Big Red down the Historic Columbia River Highway, which was a gorgeous, windows-down-music-up kinda drive, about 30 minutes from our Airbnb. The waterfall is within the Columbia River Gorge National Scenic Area, set east of the Portland on the edge of the Cascades. We'd read this was a must-see attraction for Portland travelers and it was one of the reasons we rented the car (Ubering at noon to a waterfall just doesn't sit right with me). As far as "must-see attractions" go, this was one of the coolest & most enjoyable I can recall from recent travels—it is not in the slightest a "cross it off the list" and move on ordeal. We hiked about 5 miles up & around the waterfall. The weather was amazing, it was actually sunny, and the sheer green-ness of everything was stunning - it was at this point in the trip that Katie & I became obsessed with moss. The waterfall itself was otherworldly and evoked King Kong Skull Island vibes. This was probably the coolest waterfall I've ever seen - it's also the tallest in Oregon and the most visited natural recreation area in the Pacific Northwest.

• Government Camp + Mt. Hood: Next we did a lil mini road trip to the town of Government Camp. Originally we just wanted to see Mt. Hood so started driving to a brewery at its base, which was a little over an hour from the falls in the opposite direction of Portland. Are there literally 70 breweries in Portland, the Craft Beer Capital of the World, arguably all of which would've been more convenient and economical (because gas prices)? Absolutely. Did we drive almost 3 hours round trip to drink beer near the silhouette of a mountain? Also absolutely, & would recommend. Mt. Hood, is insane to see in person. One second it's not there, then you turn a corner on the highway and all of a sudden it's the only thing you can see. It's a "potentially active" volcano, according to Wikipedia, which is an alarming description, and it's simply massive.

• Charlie’s Mountain View: 10/10. It occurs to me halfway into my second beer that the quirky little mountain town of Government Camp, situated an hour-ish outside the city, is the equivalent of Breck, or Frisco maybe, in Colorado. We got there right around après-ski and by the time we left it seemed half the mountain was inside this divey little pub - clearly a local skier's favorite. We tried a few local beers, Katie got a veggie burger & chicken tortilla soup, and I got a buffalo chicken pita wrap. Quality bar food, good beer & good vibes.

• Green Room: 10/10. This one-room bar, simple yet swanky lounge is the entrance to the large historic building that houses Multnomah Whiskey Library. Its purpose is to provide eventual Library patrons a place to eat, drink, & wait for their table upstairs in enjoyment, while dually serving as a brilliant additional revenue stream for the business. I'd never seen this setup before and thought it was so cool. We got a round of fancy cocktails & the best charcuterie board I'd had in recent memory.

• Multnomah Whiskey Library: 13/10. I will never stop talking about this place. Set in a large, dark open space with tall industrial ceilings and stunning exposed brick walls, think "hanging in your grandfather's living room," if you were living in the early 1900's and your grandfather was rich & the kind of guy who goes by Grandfather, with a capital G. It has over 2,000 bottles in its collection, lined up on floor-to-ceiling shelves that take up over 1/4 of the room's total wall space. Hence the name it's mostly whiskey, but also tequila, mezcal and other obscure nice liqueurs, such as absinthe (stay tuned). Also hence the name, it does function as an actual library with memberships for purchase - used for status, networking, and for hardcore appreciators of fine whiskey, kind of like an old-school country club. Our bartender's name was Cornelius and he was an absolute delight to banter with—Katie & I cried laughing during multiple points throughout the evening. Upon asking Cornelius for a recommendation from the Bible-like menu, the cheapest of his 3 rec's was $70 (for a 1.5 oz pour). We kindly informed him that unfortunately we'd like to aim for $20 (which suddenly seemed cheap); I ended up with a vintage, one-of-its-kind Maker's Mark and Katie tried a similarly novel Blanton's. Katie also tried absinthe (I was driving) which was a hilarious and informative experience thanks to Cornelius, and also surprisingly tasty. There was a tall chest with little mini drawers next to our table that houses notes & letters on the back of receipts from past guests over the years. Opening the drawers and reading these excerpts of strangers' wisdom brought me so much joy. Of course Katie & I wrote our own, but my favorite was from Barb & Serena circa February 2019: "Take girls trips. Studies have proven that you live longer if you dedicate time to your girlfriends."RT. Girls trip or otherwise, I would recommend this spot to absolutely everyone.

SATURDAY - URBAN EXCURSION DAY

• Queue Coffee: 7/10. Cute fancy lil coffee shop in northwest Portland. Lavender oat milk latte was fabulous, only wishing they served savory breakfast options in addition to pastries & other sweets. This is my pet peeve (Katie's too). Savory > sweet.

• Witch's Castle (Wildwood Trail hike in Forest Park): 8/10. Today's goal was to utilize Big Red for exploring Portland. We started with Forest Park, which flanks the city to the northwest and spans over 5,000 acres - one of the largest "urban forests" in the US. I did not know "urban forests" were a thing, but I couldn't think of a better way to describe the rolling greenery and sprawling trees that make up this stunning Northwest Portland hillside. We parked on a neighborhood street nearby Wildwood Trailhead and within minutes were fully immersed in this mystical PNW jungle. I'd read about a historical landmark called Witch's Castle about a half-mile from the trailhead, an abandoned stone building that dates back to the mid-1800's with ties to the Oregon Trail (cool), forbidden love, murder, witchcraft, and the first legal hanging in Oregon. The structure has likely seen more illegal teenage activities in the 21st century than haunted happenings but I do love a good ghost story. Katie indulged my interest in Weird Things by letting me read out loud the tale on my phone as we made the trek. I would recommend this activity for the sake of the hike—the forest is truly magical—a historic witch's castle is just the bonus.

• Japanese Gardens: 8/10. This is another "top attraction" for Portland visitors. I feel like it's probably not everyone's cup of tea, so live your truth, but if you're looking to enjoy a leisurely stroll while soaking in beautiful landscape and a truly tranquil ambiance, would recommend. We continued to be stunned by the versatile shades & drastic volume of green. The space was so well-maintained and thoughtfully curated, it felt like we were walking inside a snow globe, or had been shrunken to the size of gnomes and were frolicking through a fairy kingdom.

• Thai Bloom: 8/10. We were feeling Thai for a late lunch after the gardens and we also had not eaten all day (if only Queue Coffee offered savory breakfast), so we made a beeline for a restaurant-filled street nearby the gardens, still in Northwest Portland. It was a pretty standard Thai restaurant, but the food was high-quality and they had a large fun cocktail menu.

• Powell’s City of Books: 10/10. There's nothing I love more than experiencing new bookstores in different cities. Powell's covers an entire city block in the downtown Pearl District and it is the largest new + used bookstore in the world!!! It has 9 color-coded rooms, 3 floors & 3,500 sections. Popping in here was on my non-negotiable list and I promised Katie it would just be for a quick 10-15 minutes, but we ended up being equally entranced and spent close to an hour roaming through the meticulously labeled aisles.

• Buffalo Exchange: 5/10. Located directly across the street from Powell's, we popped in here for less than 5 minutes. This was my favorite thrift store in Denver before it closed during the pandemic so I thought it would be cool to visit one in Portland - also the city is well-known for a great thrifting scene, making this activity very Time & Place. Unfortunately I just really despise shopping IRL, and as much as I want to enjoy thrift shopping I just don't have the patience. If thrifting is your jam, check it out. We opted for a bar instead.

• Teardrop Lounge: 9/10. Shout out to Katie's mom for this rec! The vibe here was lively and high-end yet approachable; the teardrop-shaped bar centers the room making the ambiance light & airy. The cocktail menu checked the boxes of two menu characteristics I love—dramatic, eloquent drink descriptions + graphics signifying the type of glass the drink is served in. Katie's Moment in the Sun was "bold & bright, with a long & sumptuous arc" (mezcal, applejack, honey, lemon - served on the rocks) and my Baby Turtle was "gorgeously textured, smooth & full of flavor" (reposado tequila, grapefruit, bitters, cinnamon & egg white - served on the rocks). 13/10 recommend the Baby Turtle, it tasted like cotton candy. This bar is pricey, but the drinks are inventive enough + bartenders are personable enough that $10+ for a cocktail seemed fair.

• Hey Love: 9/10. Self-proclaimed "your neighborhood bar / restaurant / plant paradise / escape" and I couldn't describe it better myself. The interior is gorgeous and unsurprisingly teeming with green - the abundance of hanging plants + colorful eclectic decor scream Portland. We just had one drink here, a mezcal marg, but the drink menu was full of interesting cocktails as eclectic as the ambiance, and the food menu looked bomb also.

• Prost: 8/10. We met Katie's aunt & uncle for dinner at this German pub in the Mississippi District. German beers here are fab, food is authentic & delicious, vibes are divey & energetic. Recommend for a casual upbeat dinner.

• Alibi Tiki Lounge: 10/10. Katie's aunt & uncle are hilarious and adventurous and they want to keep the party going after dinner, so we we walk across the highway to this "long-lived tiki bar with island-themed murals, tropical cocktails & nightly high-energy karaoke," rightfully having earned a place in my "cool bars in Portland" research. The building's historic character (dating back to the 1800's) & dark interior evoke that Portland grunge vibe we'd come to know & love, while the tiki decor & artwork plus neon lights contribute to the energetic party atmosphere that seemingly the entire city of Portland had come for (it was packed). Because Time & Place, all 4 of us got some kinda rum drink in a funky glass. I discovered after the trip it is the second oldest tiki bar in the country, which is pretty cool.

• Moloko: 7/10. Our server at Prost recommended this spot, also within walking distance of the Alibi + in the historic Mississippi District. At this point I was exhausted and had an early flight the next morning but Katie's uncle Dan really wanted to check out the fish on the walls, and who was I to deny him that pleasure. Their website boasts "Portland's only Coral Reef Cocktail Lounge" which made me laugh out loud while writing this because, what an extremely specific claim to fame. As this tagline would suggest, this bar was lined with wavy coral reef fish tanks. Bar owners in Portland must really be like, I refuse to open a business that is in the slightest ordinary. And honestly I respect that.

& there ya have 48 hours in Portland. An infinite amount of time would surely be required to experience everything cool, but here are the key takeaways for doing a weekend right in Portland: spend your time in the city outdoors (you'll really miss the moss & greenery when you leave), prioritize experiencing the surrounding Portland natural areas, visit the weirdest bars you can find, and go to Multnomah Whiskey Library. :)