Michael and I went to Portland together last September for a family wedding. The bride and groom live in Portland and when they said they were having a local wedding I was so excited we would be able to get a quick weekend trip out there to explore. Technically, we were in Portland for 2 nights, but we kind of repeated ourselves on the second day, and only had a half day on the first, so theoretically this is all doable in one day.
Portland’s motto is “Keep Portland Weird” and we definitely got to experience some of the cities unique quirks. It seems that there aren’t very many “attraction” like things to see in the city, but what Portland makes up for that with is cute indie boutiques and delicious food. There were a couple places we missed out on due to long wait times (Pine State Biscuits, I’m looking at you) but if we were to go back I’d definitely make the time. 
The city itself feels really young and hip, and for the most part feels clean and safe. While I don’t know all the nuances of neighborhoods to avoid (though I heard the South Park Blocks are a good idea to skip), I can tell you we explored most of the downtown by foot and had a great time while doing it. 
Where we Stayed:
There are many nice hotels throughout Portland, but we found that for the location and price, an AirBNB was the better option for us. By random chance, I stumbled upon perhaps THE CUTEST Airbnb I have ever seen and managed to book it for less than our original hotel would have cost us. It was located in the Alberta District, about 15 minutes from downtown, the wedding venue and the airport, so it ended up being the perfect location for us. 
How we got around:
To get around we opted to use Lyft. While locals seem to boast about the great public transit (and that very well may be true in some circumstances) when looking how to get from several locations in the city it seemed to always take about twice as long with public transit than by driving. Due to our limited time it just seemed to make a bit more sense for us to spend a little extra cash to have more time to explore.
The Food/Snacks:
The Waffle Window & Sip Juice Bar
We started the day with Breakfast at The Waffle Window on Alberta Street, and a fresh juice from Sip Juice Bar next to Pine State Biscuits. The Waffle Window offers both savory and sweet topped waffles, on what they call a “Portland Style” waffle. The food was really great and service was quick, and the wait was A LOT shorter than Pine State Biscuits. Sip is an unobtrusive camper van turned food truck, but makes really tasty juices from fresh ingredients, highly recommend as a morning pick me up (and a sneaky way to get some veggies before those unavoidable donuts).
Blue Star Donuts
I know, everyone is going crazy over Voodoo Donuts, but I feel that if you’ve been once, you get the experience and you move on.Unpopular opinion alert: the donuts are fine, but the wait in line just really isn’t worth it in my opinion. Go once, have fun saying you’d like to order a “dirty bastard,” and move on. However, Blue Star Donuts on the other hand, are a no frills donut shop and the wait isn’t half as long and the donuts are incredible. The interior is simple but very trendy. I tried both the original and the buttermilk, and the buttermilk are to die for. So, so good and worth the trek out if you are in downtown Portland. I loved these so much I went again while in LA because I neeeeeeded the raspberry buttermilk donut in my life again.
Case Study Coffee
A really hip and chilled coffee shop that gave us just the right pick me up as we walked around downtown Portland.
Food Trucks
Portland has the most food trucks I have ever seen. It feels like anything you could think of to eat they put into a food truck, and they are everywhere. A major collection is on the Alder Street Food Cart Pod, but there’s also random pockets all over and especially at the Saturday Market. We decided to get pierogi and a Polish sausage and an “elephant ear” from ones at the Market, but really they can satisfy any craving you have.
Sights
Pittock Mansion
This mansion is slightly outside of downtown, on a big hill overlooking the city by the Rose Garden and the Portland zoo, without a car its a bit tricky to get to but it’s well worth the trek. Once you get to the mansion, you do have the option of paying to take a guided tour inside the main house ( which we didn’t end up doing) or you can go in for free to walk around the grounds. 
Saturday Market (White Stag Sign)
The so called Saturday Market, actually is open on both Saturday and Sunday. We had a lot of fun perusing all the different stalls seeing what the local artists were making and ended up picking up a really cute print (one of my favorite kinds of souvenirs to get) and a lot of tasty treats as well.
An added bonus is that the market is right on the water, so you get a super view of all the bridges of Portland and the opposite side of the river. 
Indie Shops
One of my favorite parts of being in portland was just wandering around all of the different neighborhoods and stumbling upon some of the cutest independently owned shops with trinkets and gifts that you can’t find anywhere else.
Some of the most notable for me were:
Made in PDX which was home to loads of items made locally by artisans, ranging from candles, to cast iron pans, hot sauce and wine.
Woonwinkle had some of the sweetest little items that looked super scandi inspired. The shop was really nice to browse and I felt like I wanted to take everything home with me.
Union Way isn’t really a shop as much as it is a little alleyway made up of a few independent shops and some food stalls, but it was set up so cute was like a peaceful little hove in the bustling city. 
Overall, I really loved our time in Portland and highly recommend it to anyone looking for a quick weekend trip. Obviously more is more when it comes to time but I really felt like we were able to take the city in, in the amount of time we had.
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