5 Tips for Having a Marvelously Brief Trip In Portland
To go anywhere for a short amount of time is difficult. How are you supposed to spend your time? Do you try to knock out all of the famous tourist attractions and buy a magnet? Do you just march to the beat of your own drum and see what happens? Both?
If you have a short expedition to Portland coming up, say two or three days, there are ways you can maximize your trip. However, keep in mind there aren’t any silver bullet solutions that will absolutely work for everyone.
Say, for example, you’re visiting from SoCal. A dinner at Apizza Scholls will probably be a trip highlight. But, if you’re from, say, Connecticut and have been to the famous New Haven pizzerias, it might not be the way you want to spend your limited time in Stumptown.
The point I’m trying to make is this: there are ways to do a short trip so that you, as an individual, have the best trip you can have. Here are some rough guidelines to decide how to find the places you want to hit and things you want to do in Portland.
1. Have a Theme for Your Trip
Learning how to travel for yourself is a difficult task that a lot of us must grapple with in adulthood. As a kid, you’re at the whim of your parents. As an adult, you might be traveling in the way your friends or partner likes to. While a trip is usually fun anyway, it’s important to understand what you, as an individual, are trying to get out of the soujourn.
It could be good photos, meeting people, eating good food, seeing a specific monument, finally going to that coffee shop you’ve heard so much about, or literally anything else. If you like beer, you can center your trip around beer. If you like history, you can do the same.
Before doing any online research, asking friends, or getting top-notch intel from locals, decide what it is you want to see and do. Let’s say you love wine bars and art. Now, you have a great foundation to build your trip. See what art exhibitions are in town that weekend, and maybe even ask the person in line at the coffee shop behind you what their favorite wine bar is.
Creating a “theme” or even just loose guidelines is going to make your trip more satisfying. Rather than being like “Oh, I wish I had done this or that,” you’ll feel like you accomplished what you set out to do during your foray. And, you’ll likely have a great list of other things to do or see on your next trip here.
2. When In Doubt, Look to Reddit
Honestly, Reddit is the new Google when it comes to vacation research. This is coming from someone who has worked in SEO and knows exactly what goes into writing a ranking article and how a lot of the people writing them are just gleaning info from other ranking articles on Google.
Now, I’m not saying that every Reddit user always has the best answer to your specific question. But the website is certainly a great research tool for finding different spots to hit, especially when you have a clear idea of what you’re looking for.
For example, if you’re looking for the best trivia night in Portland, there’s probably a thread for that. And, while there will no doubt be all kinds of different opinions, chances are you’ll find one or two highlights that pop up over and over again. This is a fantastic sign that these are trivia nights of note and definitely worth checking out.
3. Accept That There Will Always Be More to Do
Even if you visit a place for a month, you’ll undoubtedly have stones left unturned. Going on a weekend trip, it’s vital to accept that you’re not going to see and do it all. Sure, it’d be awesome to have the best espresso of your life, catch a record-breaking Blazers game, and randomly meet and become lifelong friends with Carrie Brownstein. But, it might not all happen on this trip, and that’s ok.
Even just wanting to hit all of the best coffee shops in Portland would be a difficult ask during a weekend trip. So, rather than having a need to do it all, just really lean into the things you do try and enjoy them for what they are.
Really dissolving into a few awesome experiences is going to leave you with way better memories than ticking all of the boxes on a checklist. The point is, don’t try to do it all and then kick yourself for not doing it all. Set out on your trip knowing there’s no way to explore every little crevice of Portland during the weekend, but also that it doesn’t mean you can’t have an amazing, awe-inspiring trip.
4. Get the Inside Scoop
Think of wherever you live or grew up and all of your favorite spots. Sure, some might be well-known destinations, but there are doubtless a good number that aren’t. The same goes for every city, including Portland.
Oftentimes, it’s the context around our experiences that gives them meaning and verve. For example, just having a random cup of ice cream might be just “fine” without context. But having a friend tell you they had the best marionberry cobbler sundae of their life at that specific creamery will make the experience more remarkable.
This all leads me to say, it can be valuable to get the inside scoop from others who know the city, not only because they’ll point you in the right direction, but also because they’ll imbue your experiences with context that can add depth.
Start with friends of friends, siblings, roommates, or whoever you might have a connection to in your life that’s lived in Portland. Even if their favorites aren’t your own, they can start you in the right direction. Once you’re in that cool bar that they love, the bartender probably has some recs for you, too.
Be open to suggestions and don’t be afraid to ask. People are usually excited to share their favorite spots, and it’s always fun to help someone else have a great trip. If you’re coming to Portland with no prior connection to the city, don’t be afraid to just ask locals about what their favorite spots are and what they think you’d enjoy.
5. Know the “Must Sees”
Like I mentioned, what will make a great trip for you will be unique. Despite this, it doesn’t hurt to know what the go-to touristy things are in Portland. Chances are, a couple of them are probably things you’ll find really fun. And, to be honest, Portland is an incredibly dope and magical city, so the attractions, ipso facto, are all pretty killer.
There’s Powell’s Bookstore, the Pittock Mansion, and the Saturday Market. If I have friends or family in, you know I’m taking them to Eem for some BBQ fried rice and brisket burnt ends white curry. Do a bit of research on some of Portland’s most popular attractions and see if any strike your fancy.
While I don’t think it’s ever a great idea to do a vacation only to get a picture at all of the iconic spots, doing it a couple of times is fun. Point is, it’s nice to have an understanding of exactly what the status quo is for a Portland vacation in order to subvert it to your heart’s content.