A trip to Portland, OR, was the catalyst that started the crazy idea to finish the 50 states in 2025. We planned a week-long trip in September with my best friend and Her Wife, and we figured since we were already flying out west, might as well cross off some other states.
We decided on Oregon because all four of us wanted a mix of city and nature but also great food. While many states in this beautiful disaster of a country can fulfill that wish, Oregon was the highest on our to do list.
Because we did so much in Oregon, I’m going to split this into two parts. Part one will be the seen days we spent in Portland, part two will be our four-day road trip around Oregon.
Day 1
Airport: Fly into PDX
The airport was in the middle of renovations when we went, and it was a far walk to pretty much everything. Our gate to the main terminal was a 13 minute walk, and then you had to find baggage and the ride share/taxi area, which wasn’t clearly marked. But it’s a gorgeous airport and they did a great job bringing the outdoor essence of Oregon inside.
Hotel: Hilton Benson Portland
The Husband and I arrived in Portland almost two days before my friends, so we had time to get settled and check out the city before they arrived. We stayed at the Hilton Benson Portland (remember, this was last September) and it was in a great spot downtown. Everything we wanted to see in that area was either a short walk or a tram ride away. It’s also a beautiful old hotel with large rooms and a historic stairwell full of hotel, and Portland, history.
Coffee: Courier Coffee
After seven hours of traveling (and it was still only noon PST) I needed a coffee. One of the many things I was excited for in Portland was trying as many of the amazing coffee shops that I could. Courier Coffee was nearby, so it was a great place to start. They roast their beans and the coffee was very fresh. They also have pastries, Japanese shaved ice, and sushi. The would later realize that most Oregon coffee shops have a special, unexpected twist that sets them apart from the rest.
Lunch: Deschutes Brewery Portland Public House
Deschutes (Pronounced Da-Shootz) is synonymous with the Oregon beer scene and are known for their delicious, crisp beers. They also have Public Houses in Portland and Bend, and it’s bar food done right. They have the usual brew pub items, such as soft pretzels, burgers, mac and cheese, fish and chips, as well as large salads and full dinner entrees. Every thing we had tasted like it was made with fresh, high quality ingredients.
Shopping: Powell’s Books
Powell’s has been my top bucket list bookstore for years! As a bibliophile and writer, I love bookstores more than the average person. I search them out when we travel and most of my souvenirs are books. I actually stopped in multiple times during our trip and could have spent days wandering all the sections.
I was most excited to visit the rare book room. It’s a small room packed with rare books, and it was thrilling to walk through (for me). They limit the number of people allowed in at a time, so you have to grab a pass at the desk outside the room. It wasn’t busy when we went, so we we didn’t have to wait for a pass.
I was tempted to buy this edition of The Little Prince to add to my collection (I buy a copy in the native language of every country we visit when I can find it) but I didn’t want to carry it around for a month and a half. So I just visited it a few times and said adieu. They also had a $15,000 edition of Nineteen Eighty-Four, which I still daydream about owning.
Wine Happy Hour: Domaine Serene Wine Lounge
One of the most surprising things I learn while planning this trip was how good the wines (specifically the pinot noir) from Willamette (rhymes with damn it) Valley are. I’m a red wine drinker, and I tend to stick to bold Italians, Côtes du Rhônes, and Napa cabs, until now. If there’s a Willamette pinot on a wine menu, I’m ordering it.
One of the more popular wineries, Domaine Serene, has a wine bar in Portland. We each did a tasting and, not surprisingly, ended up with a wine club membership. They waived the tasting fee and were able to hold the shipment until November, when we were finishing all of our traveling. The bartender was super nice and knowledgeable, without being wine snobby, and had a very impressive way of carrying the flights.
Dinner: Lovely’s Fifty Fifty
Portland is one of the most underrated pizzas cities in the US, but we had a long list of places we wanted to try. First on the list was Lovely’s Fifty Fifty. We learned about it when Chef Sarah Minnick was on the show Chef’s Table: Pizza. The menu focuses on ingredients that are available from local farmers and often include unique additions, like flowers. The pizza was incredible. The flavors blended so perfectly and the crust was that utopian balance of chewy and fluffy.
I ended the meal with a mint stracciatella ice cream and it was unreal. The mint tasted like fresh mint leaves, not artificial mint flavor. I think about this ice cream a lot (second to the rose gelato at Butchart Gardens in Victoria).
They don’t take reservations but if you get there early, you won’t have much of a wait.
Day 2—My birthday
Coffee: Case Study Coffee
I intended to kicked off my 42nd birthday with a coffee at Case Study Coffee, but their jasmine matcha was their signature drink, so I ordered that. Despite not liking matcha it was delicious. It was creamy and just a little sweet, a great way to start the day.
Coffee and Shopping: Bold Coffee & Books
Because I still needed a coffee and always want to shop for books, we walked to Bold Coffee & Books. I had a cinnamon latte while I perused the small but diverse book selection. They have all sorts of open mics nights and readings, too. If I lived in Portland I would be here often.
Snack: Blue Star Donuts
Every list we saw said Blue Star Donuts are a must when visiting Portland. One of my many hot takes is that doughnuts are overrated. I don’t generally care for sweets, and especially not in the morning. The Husband, on the other hand, loves them.
These were unique and the doughnut itself was delightful. The blueberry bourbon basil was more savory than sweet and it was one of the best doughnuts I’ve ever had. The Cointreau crème brûlée doughnut was way too sweet for me. But if interesting combinations and sweet flavors are your thing, Blue Star Donuts needs to be on your list.
Snack and Shop: Portland Farmers Market
I have never seen a farmers market as beautiful as the Portland one. All of the fruits and veggies were gorgeous! Bright colors, fresh as could be, and so many varieties of things, many I’ve never heard of.
We had pastries that The Husband loved (but were too sweet for me) and randomly the best strawberry milk of our lives! There was a farm stand that sold fresh milk in glass jars and I honestly had no idea milk could be so creamy and delicious.
I wanted to eat so many things, including the blistered peppers that filled the air with a spicy char, and giant breakfast burritos that looked like they would kill my appetite for the remainder of the day. I also wished we had rented a house instead of staying in a hotel, just so I could buy flowers and veggies. Next time.
Lunch: Ken’s Artisan Bakery
Ken’s Artisan was on our list for lunch and pizza for dinner. Like most of Portland, they’re known for their fresh ingredients and quality dishes. I know this is getting repetitive but I can’t stress enough how fresh everything was in Portland.
I had a veggie sandwich on a fresh croissant with a cup of veggie soup, and it was my dream birthday lunch. I could eat that exact meal everyday. The Husband had a focaccia pizza and it was like a gourmet French bread pizza.
Shopping: Daedalus Books
It wouldn’t be my birthday without a used bookstore visit. Daedalus Books was compact, piled high with primarily used books. The bibliosmia engulfed me like a warm hug when I walked through the door, and I could have spent all day thumbing through the pages of the books in here. Alas, we had more things to do so eventually I was forced to leave.
Snack: Salt & Straw
Salt & Straw is a local ice cream chain known for quality ice cream with unique flavors (noticing a trend?). They have some of the usual flavors, but many of them have a little added something— black pepper and blue cheese were notable unique favorites. We were the only ones there and the kind teenager working let us try so many samples. The problem with so many unique flavors that mesh surprisingly well is that it’s hard to pick one. I ended up getting a scoop of pear and blue cheese and it was delightful.
Shopping: Paxton Gate
The kind ice cream scooping teenager recommended stopping into Paxton Gate Taxidermy and Oddities, across the street from Salt & Straw. I eat a primarily plant-based diet and I can’t even kill a cockroach, so this place was not for me. But I suppose I can see how a certain kind of person would like the macabre cabinet of curiosities.
Happy Hour: Flock Food Hall
I was ready for a glass of wine, and when I saw the wine bar at Flock had a painting of a California Scrub-Jay, I knew I needed to stop. (Corvids are my favorite family of birds, and I especially love these beautiful jays.) We returned on a later day to eat here, since we had birthday dinner reservations.
Happy Hour: Oregon Wines on Broadway
This stop has a little backstory. On The Husband’s birthday the month before, we went to a wine bar in St Pete and did karaoke. While he was singing (he has a great voice!) the owner sat with me and started chatting about wine, which eventually brought us to our upcoming trip to Portland. He recommended Oregon Wines on Broadway, and told me to tell the owner that he said hello. I put this at the bottom of my notes for Portland, and forgot about it. When we got to Portland and remembered, my imbibed note-taking looked like code and I had no idea what it meant. Luckily, the bartender deciphered it (it was a list of wineries to try, written out phonetically and definitely not accurately spelled) and we ended up staying a while, trying wines with the locals.
While we were there local tour guide Nancy came in for a post-tour glass. She’s a bit older than us and far more interesting, and we were immediately enchanted. So much that we booked her walking tour for the next morning!
Dinner: GRANA Pizza Napoletana
Since we planned this trip far in advance, we were actually able to make reservations at popular places, such as GRANA. It was a popular spot before being named #25 pizza in the US, thanks to its simple, Neapolitan-style pizza, using few ingredients and lots of love.
I booked the chef’s table, which a fancy way of saying bar seating. As an amateur pizzaiolo, I liked being able to watch them create each pizza. The pizzas come out as they make them, uncut with a pair of scissors. We’ve spent many months in Italy, and I gotta say, this pizza was pretty damn spectacular. We rounded off the meal with my favorite dessert, panna cotta. It was the perfect birthday dinner.
Day 3—Friends joined us
Coffee: Stumptown Coffee Roasters
My best friend and Her Wife got in late the night before, so we went straight to Stumptown Coffee Roasters in the morning. It’s a local chain, but the coffee is delicious. We ended up having it a few times, and it was consistently great.
Tour: Best of the City Walking Tour of Portland
Full of caffeine, we met Nancy the tour guide for a walking tour of downtown Portland. Nancy is a VIBE. She was hilarious and knowledgeable, snarky but kind. One minute you were learning about the art requirements in the city (1% of city contractor budgets must be dedicated to art installations) and the next she was randomly dropping a story about hitchhiking in Buffalo in the 70’s. She was #goals personified.
We also learned about the famous Portland Benson Bubbler water fountains. These unique, four dish bronze fountains were donated by local business man Simon Benson in the early 1900s. Fresh water flows freely at all of the fountains throughout the city, similar to the fountains in Italy. Whether he donated them to keep people out of pubs or because a thirsty little girl was crying during a parade—the prevalent theories—they are a beautiful and unique addition to a quirky city.
If you are interested in architecture, art, city history, or meeting interesting people, this tour is a must.
Snack: Voodoo Doughnut
It felt wrong going to Portland and not stopping at Voodoo Doughnut, despite them being all over the country now. We’ve already established that I’m not a doughnut person, and I’ve had them at Universal in Orlando, but it ended up being one of the most exciting stops on the trip. Not because of the doughnuts—they were the same as in Orlando— but because when we got there, the area was blocked off by cops and they were running around looking for a man with a SWORD! Never have I ever been somewhere when there was man running loose with a sword. They didn’t find him but it was still very exciting.
Coffee: Deadstock Coffee
As if the adrenaline from a man with a sword wasn’t enough, our next stop was what turned out to be my favorite coffee of the trip, Deadstock Coffee. It was a small spot, basically just a counter to order, and it was decorated with sneakers! It looked like a funky Footlocker. The coffee was delicious but the cold foam was hands-down the best I’ve ever had. It was so good that my friend ordered a second coffee, just to have it.
Unfortunately, the Portland location is closed permanently (according to IG) but the second location in Beaverton is still open.
Lunch: Flock Food Hall
We were peckish but not starving after all the coffee and doughnuts, so we headed back to Flock to grab some shareable snacks. Everything was really good, and just what we needed. Food halls are so nice when traveling with multiple people, especially when you have one quasi-vegetarian/pescetarian, one gluten-free, and two with the palates of toddlers.
Bills Backer Bar: The Cheerful Tortoise
We happened to be in Portland for the Bills opening game, so we headed to the local Bills Backer Bar, The Cheerful Tortoise. If you’re not familiar with the Bills Mafia and backer bars, it’s like watching the game in Buffalo without being in Buffalo. They are always packed full of Bills fans and the vibes are 100/10. The Husband and I have been to many Bills Backer Bars, but this was one of the most fun (the best one is in London!). The wings were Buffalonian-approved and the abundant use of the Shout Song was much appreciated.
Day 4
Coffee: Java Man on Broadway
Today’s coffee was Java Man on Broadway, a plant and coffee shop. Even if you are green-thumb-challenged such as myself, it was nice to sip coffee while admiring the beautiful plants.
Garden: Portland Japanese Garden
The Portland Japanese Garden is considered to be the most beautiful and authentic Japanese garden in the world outside of Japan. It is so meticulously planned and cared for and an absolutely delightful way to spend the day. Tickets are timed and sold in advance, so it was one of the first things we planned once we had the trip finalized. If I lived in Portland, I would have a membership and spend a lot of time just sitting in the gardens with a book.
There’s a tea house in the gardens with a variety of teas, bottled Japanese drinks, and matcha. They said it was the highest grade matcha available in the US so, despite not knowing what that meant, I had to order it. It tasted like grass.
Garden: International Rose Test Garden
Located just down the hill from the Japanese garden is the Portland International Rose Test Garden. It was originally designed as a testing ground for new rose hybrids, dating back to WWI, it now has over 10,000 individual rose bushes. It blooms May to October, so there were quite a few still in full bloom when we visited at the beginning of September.
Coffee: Sterling Coffee Roasters
We needed a post-garden pick me up (since I didn’t finish my matcha) so we stopped at Sterling Coffee Roasters. They have two different coffee flights, which we ordered and shared.
Lunch: Verde Cucina
Mexican is one of the cuisines the aforementioned picky palates can agree on, so we headed to Verde Cucina for lunch. Like the rest of Portland, they pride themselves on fresh, quality ingredients. It was good, but not the best Mexican food or anything. The location in the Pearl District is a great spot to grab a bite and chill for a bit though.
Dinner: Murata
My best friend is Japanese, and her only food request was a proper tonkatsu at a Japanese restaurant. After much searching, I made a reservation for Murata. It was as authentic as they come in the US. They even have traditional tables where you sit on the floor (but your legs still dangle) but since three of us are in our early 40’s I booked a standard table. The servers wore traditional kimonos and many of the employees didn’t speak English. It was a delightful experience and the food was so good. I had eel sushi and it was fantastic. Even my normally stoic friend really liked her tonkatsu.
I took an Uber out to the airport early the next morning, picked up a rental car, and we headed out on a four-day road trip before returning to Portland.
Day 5—After our road trip
Hotel: The Porter Portland
We returned to Portland late the night before and checked into the Porter Portland. It was in a slightly different area of downtown than the Benson. The prices were great so I booked a two-room suite. It had a living room area with a huge table, which was nice for catching up on some writing.
The hotel has a mixology class every day, and we learned how to make Paper Airplanes. I don’t usually drink liquor but it was really good.
Coffee: Caffe D’arte
We grabbed coffee the next morning at the hotel store, which served Caffe D’arte coffee. For hotel coffee, it was pretty good!
Snack and Shop: Portland Farmers Market
Since it was a Saturday and my friends missed the market the week before, we headed over while The Husband watched Premier League soccer. They were just as impressed by the veggies, flowers, pastry, and that delicious milk. I swear, the market alone makes me want to pack up and move to Portland.
Lunch: Cartopia Food Carts
For lunch, we headed to one of the food cart areas. Similar to a food truck rally, except the carts are there all the time, like an outdoor food court. Like a food hall, it works well for our very specific group of preferences. I was thrilled to see vegetarian poutine at the poutine cart. There are few things as satisfying as a warm, squeaky cheese curd.
Happy Hour: Hawthorne Asylum Food Carts
Hawthorne Asylum Food Carts is a block away from Cartopia, so we popped in there for a drink. We were all full from lunch but everything looked so good. It has abandoned asylum vibes, but in a fun, Tim Burton-esque way.
Activity: Grand Central Bowling and Arcade
We had some time to waste before our dinner reservation so we went bowling, of all things. It was in a convenient spot, but it ended up being really entertaining. It seemed new and high tech, which made it easy for me to bowl with bumpers without forcing everyone else to. They also had lots of TVs with sports on, a full bar and menu (we didn’t eat), and an upstairs with arcade games. It ended up being the perfect way to waste some time.
Happy Hour: Creepy’s
We still had a little time, so we stopped in for a drink at Creepy’s, a creepily kitschy bar that is also one of the best bars in Portland. It’s weird and fun, and the bartender was awesome.
Dinner: Yum’s of PDX
In 2013, The Husband and I took a pizza tour in NYC with Scott’s Pizza Tours with Miriam, who is now the owner and executive chef at Yum’s. It felt like a full circle moment going to her pizza restaurant. And it was amazing. You could feel the love and attention that went into every detail, from the actual restaurant to every bite of food. They even offer a gluten-free pizza with fresh dough, not premade frozen gluten-free dough like most places. Since we had an early reservation before my friends left to go home to Buffalo, they still had black-and-white cookies available for dessert (they only make 12 cookies daily). They are one of my favorite cookies and were even better than ones in NYC.
Activity: Portland Timbers MLS game
The Husband is a huge sports fan but somehow had never been to an MLS game. After we said goodbye to my friends, The Husband and I walked (a long walk) to the Timber’s stadium. I love mob mentality (when it’s for good) so I can usually have a good time. I also bring my Kindle, just in case.
The Timber’s game ended up being pretty fun. When they score, a lumberjack-looking dude gets out a chainsaw and cuts a piece off of a tree at the end of the pitch. It didn’t make any sense, but the crowd loved it and it was definitely memorable.
Day 6
Bills Backer Bar: The Cheerful Tortoise
We were back in Portland for a second Bills game, although it wasn’t nearly as fun at 10 am PST. As much as I love the west coast, the country revolves around EST, and apparently so do I. After breakfast at the bar and a Bills win, we headed back to the hotel to relax for a bit.
Dinner: Apizza Scholls
Yet another Portland pizza place on every list is Apizza Scholls. It’s in a funky building, with the restaurant split in two by a stairway to the second floor apartments. Since it’s Portland, it doesn’t seem unusual at all.
Unlike the rest of the pizzas in Portland, this was more NY style. The edges were fluffy, the dough had a great chew, and the flavors were fresh and delicious (are you surprised?). It came out quick, hot, and it was delightful.
Side note: I recently read that Oregon’s climate, especially around Portland, is very similar to Italy, which is why their pizza (among other things) is so great.
Drinks: Division Wines
We popped into Division Wines for a drink after dinner. It’s a super cute bottle shop and bar, with great wine selections and a small, carefully curated tapas menu. It was quiet and unpretentious, which is our vibe. The whole south east neighborhood meshes well with us, and I would probably stay in that area the next time we go to Portland.
Dessert: Pinolo Gelato
We ended the night at with gelato at Pinolo. They had great flavors and it was creamy and fresh. There was a decent line, despite it being chilly, which is always a good sign. We tried a bunch of flavors, and loved them all.
Day 7
Shopping: Adidas Employee Store
The Adidas employee store is open to the public, as long as you have an Adidas login and make an appointment. Almost everything is 50% (some of the sneakers were only 30% off) and there’s no sales tax, so it’s a great time to stock up on favorites. We made an appointment that morning before driving over. Unlike outlets, they have new merchandise available.
Tour: Pittock Mansion
With some time to kill and our tier one activities crossed out, we headed up to the Pittock Mansion for a self-guided tour. It’s a historic mansion overlooking Portland. Like all historic, grand houses (we’ve been to so many), it was ornate and beautiful. But what really set it apart was the view of Portland and Mount Hood.
Tour: Bird Alliance of Oregon
With some energy and still some time to kill after the Pittock Mansion, we headed over to the trails at the Bird Alliance of Oregon. It’s an amazing sanctuary, with rescued and rehabbing birds and a focus on maintaining the natural environment in the area. We met Julio, their resident owl in an enclosure by the trails, and discovered banana slugs, which I could have gone my whole like without seeing and been just fine.
Coffee: Rosaline Coffee
We stopped Rosaline Coffee so I could refuel, and it was the only coffee that I didn’t really love. It was still good, but the bar is so high in Portland, and it was a bit too strong for my tastes. If you like a dark roast, you’d love this coffee. And they have the cutest bird wallpaper, which I obviously loved.
Tour: Mill Ends Park
Our last stop before dinner was a tour of Mills End Park, the smallest park in the world! It’s literally a tree in the middle of the road, and our tour consisted of driving by. But it was on many of the Portland tourist lists, so we had to see it.
Dinner: Ken’s Artisen
Our final dinner was Ken’s Artisen for pizza Monday. At the small annex next to the bakery, they serve pizza on Mondays from 4-9. That’s it. So if you want to get their pizza— and trust me, you do— make sure you’re in Portland on a Monday and get there early.
The vibes were very much like a small pizza shop owned by a nonna in Italy. Everyone seemed to know each other and everything was delicious. The dough was perfection and the ingredients were so fresh. All the pizza we had in Portland was incredible, but if I was forced to pick a favorite, it would be this one. I think.
Day 8
Airport: PDX
We had an early flight out of PDX to our next stop Salt Lake City. Despite the ungodly hour, both Stumptown Coffee and Blue Star doughnuts at the airport were open, which helped my grumpiness tremendously. Since retirement a few years ago, setting an alarm is no longer in my daily repertoire and I’ve grown to enjoy slow, quiet mornings.
Despite the long visit, there were still tons of places we wanted to go to but didn’t have time. Many were bakeries where you have to get there super early, like JinJu Patisserie, and others just didn’t work because there are only so many opportunities to eat in a day, such as Lardo, Gado Gado, and Scottie’s Pizza Parlor.
Despite the national narrative saying otherwise, Portland was a clean, friendly, safe city. Like any other densely populated area, there were some unhoused people, but they never said a word to us. They were polite and didn’t hound us for money, like in other areas. If you’re hesitant to visit, don’t be. I think you will be absolutely delighted by the city.
And if you read this far, please give me a like below! This took me hours to write, and my love language is positive reinforcement.