Portland, OR

Updated: Sep 20, 2023

Our itinerary

Day 1

It’s just our luck that the one time we get to the airport early our flight gets delayed. My money’s on Alec being a bad luck charm when traveling (but I still love him anyway)! When we eventually landed in Portland around midnight, we were both super tired but ready for a fun-filled weekend exploring another new city together. Once we got off the plane we hopped in a shuttle to take us to the Thrifty rental cars lot. Of course there was a check in line at 1am so we had to wait a bit & once we finally got the keys to a brand new 2021 Ford F150, we realized it was dead. After Alec switched out the keys for a new truck (& got our gas compted) we were finally off to our hotel. It was about a 20 minute drive there, so we arrived around 2am. Sadly our hotel didn’t have a parking garage or lot, so we quickly found street parking & checked in. Once we finally made it up to our room, we were ready for a great night’s sleep in ac with black out curtains to help us sleep ‘til dawn!

Day 2

Saturday morning we decided to sleep in because of our late night of travel the day before. We got up around 11am (which is insanely late for us) & got ready in a hurry. We drove over to eat breakfast at Pine State Biscuits which was seriously the best! We waited in line for about 30 minutes before getting seated but it was so worth it & the food came out super quickly. Alec and I both ordered the Reggie + a Bourbon Caramel Cinnamon Role & their house coffee of course. After devouring our delish breakfast we went over to our first brewery of the day. We had originally planned to do a scheduled brewery tour through Brewvana, however it got cancelled last minute due to Covid restrictions. Due to that, we decided to make our own “brewery tour” around the city starting at Capture Beer Bus. It was located in a super cute food truck area with tons of food & drink options to choose from. I had the Party Time Lager & Alec ordered the Kolsch. Both were super tasty & we loved sitting outside, soaking up the sun in their picnic area in the center of the trucks. Once we finished our beers, we headed over to Rogue Eastside. I ordered the Rogue Spirits Cranberry Elderflower Vodka Soda & Alec started with the Outta Line IPA and then the Honey Kolsch next. Last on our self made brewery tour we stopped at Deschutes. Alec branched out & tried the Obsidian Nitro Stout & I got the Spiked Marionberry Lemonade. We loved the atmosphere & drinks at all 3 places, all very different & unique compared to the others but my fave drink by far was from Rogue Eastside.

After A&B’s Brewery Tour, we went back to our hotel to change + freshen up for dinner. We drove over to McCormick & Schmick’s Harborside at the Marina which was only about a 10 minute drive. Luckily our hotel was in a perfect location & super easy to hop on the road & get from place to place. Alec got the Rib Eye & I had the Parm Crusted Chicken. Both were super tasty with a gorg view of the marina which made for the perfect evening. After we finished our meals we just HAD to order the Marion Berry Pie which was absolutely to die for!! Once we wrapped up at dinner we drove our car back to our hotel to park & walk over to Teardrop. Portland is certainly known for the brews & bars because all the places we went to over our visit were SO cool. We both got some fancy drinks from the bar & enjoyed talking the night away.

Day 3

Sunday morning was a big day for the Stegalls. We had a Franklin family tradition that became a Stegall family tradition once Alec & I got married, which is donut Sunday. Every Sunday, without fail we have to get donuts so of course our trip to Portland could not stand in the way of that. Luckily Portland is home to Voodoo Doughnuts, so after we grabbed a house brewed coffee & Rose Gold Latte from Stumptown, we walked over to grab our doughnuts. It only took us about 15 minutes to get to the front of the line & pick out our half dozen. We got the famous Voodoo doll, 2 glazed, an Old Dirty Bastard, Maple Bacon Bar, & of course a Homer. After paying (they accept cards now, used to only accept cash) we walked back to our hotel lobby to enjoy our delicious breakfast!

Since the weather was a little colder & rainer than we anticipated (no complaints here though, we love the rain & haven’t seen much of it since moving to CA) we made a quick pivot & went to Grand Central Bowl. We started with 3 rounds of bowling while also watching the mavs game on their giant tv screens. We order some beers & mimosas + spinach artichoke dip & chicken tenders to munch on while hanging out. Once the game was over (& the mavs sadly lost the first round of playoffs) we decided to head upstairs to play some arcade games. We quickly forgot about the mavs lost once we started playing the Jurassic Park game & acting like we were kids again. It was seriously our favorite part of the whole trip!

After we had our arcade game fix we went back to our hotel to relax for a bit before dinner. Fun fact about Alec, he is obsessed with slow Jazz music & has been dying to go to a concert but sadly Covid has gotten in the way of that one too many times. So when I finally found one that was open I was stoked to surprise him & go there. Sadly 1905 only has musicians play some weekdays to avoid bigger crowds but the food,drinks, & atmosphere were still so good. For drinks I ordered an Aperol spritz & Alec got a Mexican Lager to accompany our garlic knots & truffle pizza. After dinner we once again drove back to park our car close to the hotel before walking over to a strip with lots of unique bars + restaurants. We first stopped in River Pig Saloon for a drink + to watch a soccer game then ended the night at Too Wrongs before heading back to our hotel to crash into our bed for the night.

Day 4

Monday morning we packed up & dropped our bags off at the front desk before adventuring out for the day. We wanted to grab a quick bite to eat + a coffee before heading to the zoo, so we stopped at Bowery Bagels. I got the Dan breakfast bagel & Alec got the John Fremont breakfast bagel & then of course 2 black house coffees to go. We drove over to the zoo to park our car + eat before heading in. The Portland Zoo isn’t that big so it only took us about 2 hours total. We got to see tons of action because most of the animals were up & at ‘em which was super cool. We also got to see some black bears (like we did in Yosemite ) and I decided they aren’t so scary after all ;) After we finished wandering around the zoo we headed to Powell’s Bookstore, which is the world’s largest independent bookstore. You could literally spend all day in there if you had the time, they have so many books & sections to explore, it was crazy! After finding one of Alec’s all time favorite kid’s books for our future child, we checked out, & headed to grab a bite to eat before going to the airport. We stopped at Afuri for some tasty ramen bowls + pot stickers & a couple of refreshing drinks. Of course we couldn’t end the meal without stopping for some dessert, so we drove over to PDX Cookie Co to grab some sweets to go!

What to wear

Friday’s travel outfits-

A: beige shorts + green shirt + black sneakers

B: + green pants + graphic tee + vans

Saturday’s day outfits-

A: blue striped shirt + canvas khaki joggers & white sneakers

B: overalls + white short sleeve bodysuit & vans

Saturday’s evening outfits-

A: black jeans +purple button up with white under shirt + white sneakers

B: black jeans + zebra top + vans

Sunday’s day outfits-

A: canvas khaki joggers + blue striped top & white sneakers

B: green pants + black crop tee + vans

Sunday’s evening outfits-

A: canvas khaki joggers + leaf print shirt + white sneakers

B: black jeans & black crop tee + vans

Monday’s day + travel outfits:

A: canvas khaki joggers + grey tee & black jacket with black sneakers

B: overalls + black crop tee & portland sweatshirt with vans

Where to stay

We stayed at the Canopy by Hilton & were completely obsessed. It was such a cute boutique style hotel with all the amenities of a chain. Check in was at 4pm & check out was at noon, free of charge, which is SUPER rare. All the employees were super friendly + knowledgeable which made our stay even better. It definitely would have been nice to have a parking garage or lot for all the guests but we were able to make street parking work. You just have to download the Kitty Park app & set up payment then the rest is a piece of cake. Obviously Portland is also known for having a larger homeless population & we definitely did see a lot of that however, no one ever approached us or bothered us at all. We were just advised (& would advise the same thing) to drive/Uber most places instead of walking & to not stay out too late after dark. Other than that we had an incredible trip exploring another beautiful U.S. city as well as checking off another state on our bucket list, which now puts us at 23 out of 50 states!