Portland in a Weekendfeatured
I have this little hiding spot. This serene little stretch of beach that I hide away to, where I won’t know anyone and no one will know me, and where I can sit for hours and listen to the waves lap up against the shore completely uninterrupted. All concept of time slows down, screeching to a halt while I’m in my hiding spot. It’s just me, the beach and the ocean. Sometimes, I think that’s how it’s meant to be…where I’m meant to be.
Unfortunately for me, though, this little hiding spot? It’s on the other side of the country.
See, I used to go to Seattle a lot for work and after my first visit, I was absolutely in love with the Pacific Northwest. It was just so…different…than Chicago. The pace, the culture, the people, all of it. Sometime a few years back, I decided to extend one of my work trips to the weekend and rent a car to visit another stretch of the Pacific Northwest to see if it held the same magic Seattle did. Destination? Vancouver, maybe. Or Portland. But a friend of mine had taken a trip down the Oregon Coast, and I fell in love with it through his pictures. I just had to see it for myself.
So I extended my next trip out west through the weekend, and on a Friday afternoon after work, I rented a car and drove myself down to Seaside, Oregon. And the rest is history. I’d go off on one of my quarterly Seattle trips, leaving Chicago for the Pacific Northwest on a Sunday morning, I’d work sunrise to sunset for the week and then on Friday, I’d rent a car and drive down to the coast, coming back to Seattle on Sunday in the late afternoon for a flight back home. I did this a number of times. I never shared it, or wrote about it. I probably posted some pictures on Instagram. My trips down to Oregon, spending the mornings sipping coffee at a café in Cannon Beach, spending the afternoons cruising the coastal route with the windows rolled down and the evenings on that beach in Seaside – they’re memories that are so incredibly special to me that I’ve always kind of kept them to myself. It’s almost like they were this one-of-a-kind blanket that I could pull out and wrap myself in when I needed an extra dose of tranquility.
I transitioned into a new role at work last year, one that didn’t need me in Seattle anymore, and so ended my post-work adventures to the coast. For awhile, anyways. Towards the end of fall, Stephanie was really aching for a weekend away, and since my work (online retail) always gets a little crazy in November and December (go figure), I couldn’t say no to a quick little getaway. She wanted to go somewhere new. I just wanted to go.
We ended up in Portland.
On all of my trips down to Seaside and the coast, I never actually made it to Portland. I had plans to, but I’d find myself losing track of time on that beach. And deep down, I knew I probably needed more than a couple hours to explore — I knew I’d want at least a little more time to savor it all. The most similar city I could connect Portland to was Austin and I love, well, just about everything about Austin. And since we were extending our weekend in Portland through Monday afternoon, it gave me a day to show my sister the Oregon Coast and share with her everything that makes it so special to me.
Spoiler alert: she fell in love, too.
So we flew out on a Friday afternoon (fun fact: the TSA doesn’t like it when you attempt to stay dialed into conference calls while you’re passing through security) and we flew back late Monday afternoon. In between, we explored some of Portland’s most famous sites, drank way too much coffee, explored the Oregon Coast and….toured a cheese factory? Read on.
Getting to Portland
Getting to Portland was pretty easy: all major US carriers fly there, including my preferred airline, American, which offers twice daily non-stop flights from O’Hare (my home airport). I’ve noticed, though, that flight prices to Portland are almost always trending high compared with flights to other West Coast destinations, and where flights to nearby Seattle can often trend lower, it’s an easy two-hour drive between the two.
The public transit system in Portland is surprisingly expansive for the moderately-sized city it supports, and there’s a train that runs directly from the airport to downtown in under 40 minutes for something around $2.50. Because we planned to drive the coast, though, we just rented a car. Stephanie and I will rent a car in just about every city we visit (except for NYC) regardless, but it’s worth noting that if you don’t want the hassle or added expense of a rental car, Portland is extremely easy to get around via public transit. But if you do rent a car, the car rental center is in the airport (always a plus when you don’t need to take a shuttle to get there!) and has a pretty neat model of Multnomah Falls made out of Legos.
The PDX airport (which sports some awesome 1990’s Cineplex Odeon-esque carpeting that has almost become emblematic of the city) is located 12 miles outside of downtown, about a 20-minute drive that feels infinitely longer after a four-hour flight. By the time we got in, it was past 8:00 PM and it was pouring, so we grabbed some food from a Jack in the Box drive through (we don’t have it at home, so it went with my try not to eat what you can eat at home rule for traveling). They offered something called a Munchie Box, which has a bizarre assortment of items that I can only imagine is the greatest thing ever if you, you know, have the munchies. We were just tired after the long flight and settled on burgers and fries and ate in the parking lot because that’s just how we travel.
Accommodations
When we were planning this trip, Stephanie and I went back and forth on whether we wanted to stay in Portland or on the Coast. Every time I’ve visited the coast, I’ve stayed at this cute little hipster hotel on the beach in Seaside called the Ashore Hotel. They have fireplaces in the room, a bonfire pit downstairs, complimentary organic coffee in the lobby (along with a not complimentary but surprisingly expansive beer and wine selection at the lobby bar) and free bikes for use. And it’s literally steps from the beach. I could go from my room to toes in the sand in under five minutes.
Since we wanted to spend the bulk of our time in Portland this time, though, we decided to stay at a hotel downtown. We ended up at the Hi-Lo Hotel, and, you guys, it was like the hotel of my Instagram dreams.
The Hi-Lo is a luxury boutique hotel in the Marriott portfolio, located in the historic (and renovated) Oregon Pioneer Building. Small touches harkening back to the history of the building still exist (like the mail drop in the lobby and the exposed concrete in the hallways), but the hotel is otherwise modern (opening rather recently in 2017). The entrance to the hotel reads Welcome, Wanderer and from the moment we entered, we truly felt at home. The lobby is an open space, with a bar on one side, a sitting area with gauzy drapes, a swinging bench and wall tapestries on the other and a check in desk next to a small commissary. It’s a comfortable space to grab a drink or meet a friend, but it’s also visually just very beautiful. I just wanted to take pictures of every part of it.
We booked the hotel as part of a flight/hotel package through American Vacations (a great way to accumulate extra miles, because they often offer bonuses!) and I think we were booked in a standard room, which had a super comfortable king bed (decorated with a distinctive Pendleton Woolen Mills accent pillow – a touch that added an extra boost of PNW-feel to the room), a flat screen LED television and a large tweed couch. The bathroom featured heated floors and a large walk-in shower. Locally produced Maak Lab products were available in dispensers in both the shower and by the sink.
The room was immaculately clean and luxurious in a way that felt comfortable and homely, but it was really the small touches that stood out. There was wood paneling on one of the walls made from locally reclaimed wood from Pioneer Millworks. The coffee station on the desk offered Starbucks coffee and Tazo tea, but also complimentary bottles of Essentia Water (that fancy ionized alkaline stuff!). The closet had plenty of space to hang our coats and clothes, but also some super fluffy bathrobes, and instead of a traditional Do Not Disturb sign, there’s a knotted rope you hang on the door.
The only downside to the hotel was the parking cost (which is one of the reasons I don’t entirely love staying in downtown areas). The hotel (like most hotels in downtown cities) doesn’t have it’s own self-parking garage, and parking rates were pretty high ($43 daily for valet). The plus of staying in a downtown area, though, is that SpotHero exists and we found parking in a lot across the street for less than $20 a night.
Things to Do and Snap
Filling an entire weekend of things to do in Portland is easy. I could probably spend a week there and find new things to marvel at and enjoy every single day. We didn’t have a week, though, and since we were planning on spending a full day on the coast, we didn’t even have an entire weekend. With a day and a half to devote just to Portland, we had our work cut out for us to find the best parts of the city to explore on an abbreviated schedule, but I think we made the most of it. A few of my faves from our weekend…
Multnomah Falls
A short drive outside the city is one of the most majestic waterfalls in the United States. Spanning more than 600 feet, Multnomah Falls might be one of the most iconic I-Was-in-Portland pictures on Instagram. And as pretty as it is on the IG? It’s even more stunning in person.
Waterfront Park
I’m a sucker for waterfront anything (I’ve never lived more than two blocks from Lake Michigan the entire time I’ve lived in Chicago!), and Waterfront Park is the perfect place to take a stroll in Portland. Situated right in Old Town (right across the street from the iconic Portland Oregon neon sign), Waterfront Park is the perfect spot to walk along the Willamette River, snap some pictures and during cherry blossom season, you can even admire the blooms. We missed cherry blossom season by a few months, but we were treated to some gorgeous fall foliage!
Pittock Mansion
Supposedly haunted, the Pittock Mansion is a French Renaissance-style mansion that sits atop the West Hills overlooking the city below. You can tour the house for $12, but if you’re not into architecture, ghosts or local history, you can roam the grounds for free (which is totally worth the drive up, if for nothing else, the view of the entire city below!)
Powell’s Books
Nine rooms, 35,000 sections, a million books. Powell’s is the world’s largest independent bookstore, and you could easily spend hours wandering the different rooms (the store is so big, it takes up a full city block – they’ll provide a map if you aren’t looking to get lost), sipping coffee and browsing locally produced souvenirs.
Crystal Heart Books
A small store that features any kind of crystal, healing stone or incense you could ever want, Crystal Heart Books also offers aura photography, where you place your hands on biofeedback plates that allow a special camera to pick up the colors of your aura. These colors, their placement and direction can reflect your physical, mental and spiritual state. It sounds kind of crazy, I know, but it’s also SO much fun (and, for the record, I’ve done readings in New York, Portland and Chicago now, and all three have been crazy accurate!). Also crazy – my aura wasn’t too different from when I had it photographed in New York a couple of months earlier, but Stephanie’s aura was almost identical!
Portland Cider House
Portland is a great city if you love beer, with dozens of breweries you can tour and taste your way through. I’m not a beer girl, but thankfully for me, Portland also has some great cider places. My favorite was the Portland Cider House, which has a fun, low-key tasting room that offers more than 30 ciders on tap and a fun, laid back space to enjoy them in.
Cathedral Park
Beneath the magnificently beautiful St. John’s Bridge, the tallest bridge in Portland and one of the landing spots of Lewis and Clark in the 1800s, Cathedral Park is a quiet spot tucked away in a residential neighborhood. The park is lovely and so picturesque, especially in the fall. I was completely taken by the symmetry of the space from under the bridge. I must have taken a dozen pictures of it!
The Eats
The food in Portland…where do I even begin? If you’ve read enough of these, you’ll know that I love food. Seriously. I love food so much that I’ll make travel plans around the things I can eat (I literally went to Denver for my birthday a couple weeks ago so I could have queso at Torchy’s Tacos). But how do I put this…as much as I love food, I’m not the kind of girl that travels for fine dining experiences or really wants to get all dressed up and fancy like when I’m traveling over a long weekend. When I’ve only got a few days in any given place, I want to spend my time immersed in the place I’m visiting, and I really just prefer the casual places that lack pretense and where I can really experience the city I’m visiting through it’s food. Luckily for me, Portland’s food scene was robust in options and cuisines. Everything was a little quirky and different, just like the city they’re located in, but everything I ate – literally everything – was so good. If you’re planning a visit, here are my favorites:
Hunnymilk
If you’re anything like me and you constantly find yourself torn between savory and sweet dishes when you’re out to brunch, Hunnymilk is perfect because you don’t have to choose! The brunch menu is at a fixed price and allows you to mix and match one savory dish with one sweet dish and one beverage. Drinks are served in vintage children’s cups and there’s crayons and coloring sheets at the table, but don’t let that fool you. The fare is gastronomic takes on brunch favorites. Get the Baked Eggs Surprise with the truffle hollandaise and thank me later.
Pine State Biscuits
Hearty twists on a classic breakfast staple. It’s hard to do biscuits wrong, but Pine State Biscuits just does them so right. Come hungry, though – the portions are huge and the biscuits are dense. You won’t be hungry for lunch.
Voodoo Doughnut
A cult favorite at the location that started it all. Voodoo Doughnut has this mystic allure (and more than 50 rotating flavors). The line is almost always out the door, but it moves fast. Pro tip: know what you want before you reach the register (their Web site lists all of their flavors) because trying to figure out what you want on the spot can be overwhelming with so many choices! And when in doubt, go for the Voodoo Doll (their flagship pastry) or the Maple Blazer Blunt (my personal fave!).
Blue Star Donuts
A little more traditional and refined than the sheer baked insanity at Voodoo Doughnut, Blue Star donuts are a little more on the savory side, with a texture that’ll melt in your mouth.
Cruz Room
A fun bar slash taco joint. How much fun? They put little plastic dinosaurs on their cocktails, and if you don’t think that’s fun, we can’t be friends. The tacos are primo, too. My favorite was the Sweet Caroline, a pork taco topped with honey mustard slaw. Stephanie dug the Fresh Prince, a Philly cheesesteak taco.
Afuri
I don’t know if it’s because of all the rain and the fog, but Portland just kind of feels like a ramen city and Afuri does it oh so well. The broth is full of umami goodness and the noodles? Handmade in store. Doesn’t get much better than that.
Never Coffee Lab
Great coffee that’s elevated above the regular macchiatos or cappuccinos (though they definitely have those, too!). I really enjoyed the Hug, a fiery coffee concoction with spicy cacao, cinnamon and smoked chiles. Added bonus: the monochromatic signage with pops of bright primary colors. You know I’m a sucker for pretty spaces.
Cheese & Crack Snack Shop
I have two words for you – bruleed brie. Cheese & Crack is a cute little snack shop that focuses on (shocker) cheese plates. They look amazing. Like, visually, they’re beautiful. Everything on it tastes even better. Months later and I’m still dreaming about them to the point where I have a fare drop alert on flights to Portland just so I can go back and have more cheese. I’m not even kidding.
BONUS: A Day Trip to the Coast
Even though we were staying in Portland, a drive down to the Oregon Coast to spend a day meandering through some of the most beautiful coastal towns couldn’t have been easier. While I usually drive a straight shot down from Seattle, there’s also a route that took us in a full circle from Portland that hit all of the spots I wanted to show Stephanie.
We started the day before the sun even came out, getting an early start with an hour and forty-five minute drive to Astoria, which was the first stop on our day on the coast. Once we cleared Portland, the landscape shifted from urban city to sky-streching Douglas Fir trees. We crossed from Oregon into Washington and back into Oregon. The morning fog was rolling in as we traversed the Lewis and Clark bridge, adding a little extra ambiance to our drive. The landscape is stunning beyond any words I could write for you – I could drive through it with the windows down for hours.
By the time we made it to Astoria, the fog had lifted and the sun was peeking through. Astoria is a coastal city situated on the Columbia River. It’s a popular port of call for cruises sailing along the Pacific Northwest and it’s just filled with cafes, breweries and boutiques. You could make a full day shopping, tasting local brews and eating at any of the dozens of restaurants. I’ve done it and, five out of five, would recommend. There weren’t any ships in port on the day we visited, but I’ve been in town when a ship is in dock and it just lights up with all that energy. Astoria is the perfect port town, easily walkable and a ton to explore.
Because Astoria was our first stop of many and we arrived in the early morning hours of a quiet fall Saturday, I had two things I wanted Stephanie to experience. First was a walk down the old train tracks along the water, where you can see (or on our morning, just hear) sea lions, breathe in the crisp morning air and see the Astoria-Megler Bridge, the longest continuous truss bridge in the country. It’s not quite as massive as the Golden Gate, but I kind of have a thing for big bridges (see: Nicole Does San Francisco and Stares at Bridges, parts 1, 2 and 3) and it’s bigger and more beautiful than any bridge we have at home!
The second thing was brunch at my favorite café on the coast, the Columbian Café. On my first trip out to the coast, one of my pals in Seattle told me that the Columbian Café was her absolute favorite, and I’ve made it a point to visit on every visit out to Oregon (on some of them, I’ve even stopped here twice, for breakfast on my first day and breakfast on my last on the way back up to Seattle!).
The Columbian Café is a small, cash-only restaurant that doesn’t take reservations, so I’ve always shown up early in the morning because the locals start lining up before it even opens! There are a few booths in the café’s small dining room, but I always try to snag a bar seat in front of the open kitchen. The bar is the perfect spot when I’m flying solo, but it’s also great when you’re traveling as a duo because you get a front row seat to watch the chef work his magic. While the Columbian Café has a rather expansive menu, they offer a unique option – the Chef’s Mercy – where the chef will create a dish for you at his whim. You tell him any restrictions (no seafood for us) and what level of heat and spice you’re comfortable with and the rest is in his hands! We ordered one Mercy and one chicken hash and as we waited, we poured over our coffees, munched on the freshly toasted sourdough that appeared in front of us with a tray of locally-produced savory jellies (the garlic was my favorite, but Stephanie really dug the pepper jelly) and speculated on which dish would be ours every time the chef started working on a new ticket. Our Mercy ended up being an egg scramble with bacon, spinach and chanterelle mushrooms served atop a fresh crepe, and we couldn’t decide if we liked the Mercy or the hash better – both were spectacular.
Full and ready to explore, we hopped back in the car and headed off to Seaside. Seaside is your stereotypical beach town, with a boardwalk that runs along the beach and a town full of small beach-themed shops (including a little shopping mall with a carousel!), arcades, candy shops, even a retro ice cream parlor inside a throwback store (which might be my favorite dessert spot in Seaside). Seaside is the perfect place for family fun, but it’s also my favorite spot to hide away at. Sitting on that beach, I could lose myself for hours staring out at the waves. Those sky-high fir trees peek over the ocean off in the distance, and the combination of ocean air with the grassy smell of those trees? It’s just the best.
Cannon Beach was our next stop, just a short drive from Seaside. Perhaps most famously known as the place The Goonies was filmed, Cannon Beach is another beachside town filled with, you guessed it, boutiques, breweries, cafes and coffee shops. These places all sound similar, but the vibe in each of them is distinctive and unique. Astoria has that small town charm, Seaside is full of high-energy family fun, and Cannon Beach is a little more upscale and quiet.
If we hadn’t already eaten breakfast, I would have taken Stephanie to the Lazy Susan Café for their famous poached eggs (which are covered in Tillamook cheese and are sooooooo tasty!). Instead, I took her for a walk around the beach to see Haystack Rock, a 235-foot rock formation that juts out of the Pacific Ocean, not far from the shore. During low tide, the rock reflects up off the shallow waters along the shore and makes for a really fun photo op.
Before we left Cannon Beach, we made a stop at Sea Level Bakery, my favorite area coffee shop, for cappuccinos and some of their homemade sourdough toast with honey and sea salt. I don’t know why, but the coffee shops in the Pacific Northwest (and especially in Oregon) are just so much better than any I’ve found anywhere else in the US. The coffee is better, the ambiance is so much more relaxed and the people are so easy going.
Our final stop in Tillamook was about an hours drive away, but the drive between Cannon Beach and Tillamook was almost like an extra stop in and of itself. It’s probably the most scenic part of the drive, with a handful of scenic overlooks to pull off on. My favorite one is near Oswalt West State Park where, on a clear day, you can get a good view of Smuggler Cove. The rain that had been threatening to fall all morning was threatening to make an appearance, but I thought the cloudy skies and fog just added to the experience.
Normally, I’ll make a stop in Rockaway Beach in between Cannon Beach and Tillamook for shaved ice and vintage shopping, and another in Cape Meares to visit the lighthouse, but the weather was just getting worse and we wanted to be back in Portland before dark, so we skipped the extra stops and drove straight to Tillamook.
Most people will associate Tillamook with cheese, and since we’re from the Midwest, where cheese is basically it’s own food group, we had to visit the recently renovated Tillamook Cheese Factory, where you can explore the history of the brand, watch cheese being made and packaged and taste alllllllllllllll of the samples we could handle. The Tillamook Cheese Factory is super-family friendly, but also super fun and friendly for two adults who just really love cheese. Basically, it’s fun for all. If the weather had been better, I would have taken Stephanie down the road to the Blue Heron French Cheese Company (where they don’t produce their own cheeses but sell hundreds of different kinds and have a primo café AND a petting zoo). At this point, though, the sky opened up and drenched all our other plans, so we settled into the café at the Tillamook Cheese Factory to munch on grilled cheeses and cheese curds (and if we weren’t driving, they also offered a ton of locally produced ciders).
When the heavy rain reduced to a drizzle, we started our drive back to Portland. We listened to Free Bird (our favorite road trip song) and marveled at the trees and how beautiful the coast was and that was it. It was the perfect way to end the perfect day.
Have you been to Portland or the Oregon Coast? If you have, I’d love to hear all about your favorite places to eat and things to do!
