Top 10 Things To Do In Portland!

Sometimes being a Real Estate Agent also means being a bit of an unofficial tour guide to the city I call home. It makes sense when you think about it. I spend a lot of time out and about looking at homes and I get to know individual neighborhoods really well over time. I feel rather proud to be living in Portland and one of my favorite pastimes is discovering all the activities this city has to offer.

Keep in mind, this list is purely subjective. If you ask twenty different people what their favorite things to do in Portland are you will probably get twenty very different lists with hardly any overlap in opinions. Heck, it took me quite a while to limit my own list down to only ten items. There is a lot to see and do here! So without further delay here are my top ten things to do in Portland in absolutely no particular order.

1. Go Eat Ice Cream

I love ice cream. Of all the indulgent sweets a person can treat themselves to (chocolate, cake, pie, etc.) ice cream is probably my favorite. The thing is I like good ice cream. None of that Baskin Robbins, Cold Stone, or other overly processed mush people like to pass off as honest to goodness ice cream. Thankfully in Portland, off the top of my head I can think of not one, not two, but three absolutely amazing ice cream businesses with multiple locations across the city.

Ruby Jewel Ice Cream

Have you ever wanted to try a sorbet with edible flowers and iris liqueur? Well then head on over to Salt and Straw! How about a rhubarb vanilla ice cream? Then Ruby Jewel is going to be your jam. How about a blood orange creamsicle? Sounds like Fifty Licks is going to be the place for you. It doesn’t matter if it is the height of summer or the middle of winter, all of your ice cream fantasies will be fulfilled at any of these three options. Just be prepared to wait in line a little bit. I promise it is worth it though.

2. Sit and Chill At A Coffee Shop

The people of Portland like to slow it down. We’re experts at putting the cares and stress of modern life into the back of our minds and soaking in a little atmosphere and comfort drinks. It should be no surprise then that Portland has a lot of coffee shops. I mean A Lot of coffee shops. We have cozy coffee shops and modern trendy coffee shops. Big chain coffee shops and locally owned coffee shops. Coffee shops designed to give you your caffeine fix quickly and coffee shops that encourage you to prop up your feet and relax for an hour or two.

Portland Coffee Shop

My two personal favorites would have to be Water Avenue Coffee for sheer quality of the brews they serve and Stumptown Coffee Roasters for their relaxing atmosphere and easy accessibility. No matter where you choose to go however, a coffee shop is a great place to spend some time, recharge for a little while, and soak in the neighborhood.

3. Go To The Movies

I love going to the movies. I especially love going to the movies when I have the opportunity to see something unique. Sure, I like a good Hollywood blockbuster every now and then, but the experiences I find truly rewarding are the times when I can go see a film not knowing what to expect, or knowing that the experience isn’t something I can just pull up on Netflix a few months down the road.

With all of that in mind, Portland has you covered. A great place to start is the HollyWood Theater in North Portland which often features classic films in rare 35mm and 70mm prints. Want something really different? Check out the Church of Film which features very hard to find and international art house films to the viewing public. Believe me you aren’t going to find any of their films on a streaming service. Or if you are feeling really brave, check out the longest running live experience of The Rocky Horror Picture Show at the Clinton Street Theater in the south east quadrant of PDX.

4. Play Some Pool!

Maybe I saw The Color of Money at way too young of an age, but I love playing pool. I especially love playing pool with a pitcher of beer and some close friends. I’m not going to make the claim that I’m particularly good at pool, but it’s really just about some friendly competition with people you care about.

Backstage Bar Portland

My favorite place to play pool in Portland is without a doubt the BackStage Bar in the trendy Hawthorne district. This place just oozes with atmosphere and good times. Seasoned pool sharks mingle freely with more casual players and you can choose to play out in the main hall or in one of the more cozy back rooms. Pool not your thing? They have some really epic shuffle board on the property as well!

5. Enjoy A Park

Sometimes people smirk at me whenever I suggest hanging out in a park. Yes, I get it, it’s not the 1950’s anymore and in this fast paced day and age just simply hanging out at the park can seem a little boring. However, as far as I’m concerned, when you combine a picnic blanket, a good book, a delicious sandwich, and some spring sunshine and you’ve got a recipe for a great afternoon. Portland, with all of its emphasis on community will take that a step further and on summer night you can attend movies in the park, community plays, and even culinary events.

If you are looking for a park with space to wander, soak in a few ponds, and hang out with ducks and birds than Laurelhurst Park is going to be your jam. Washington Park is right in the heart of the city and will lead you to such attractions and the International Rose Test Garden and the Japanese Garden. If you are willing to venture up north just a little ways, then Cathedral Park will provide some epic views of the St Johns Bridge and the Willamette River.

6. Eat Something Unique

Really, there is just way too much good stuff to even know where to begin with this one. Portland is a great destination for those who want to experience food. I would personally put Portland’s food scene up against any other major metropolitan city, including New York. I’ve been living in Portland for well over a decade now and I’m still discovering new and amazing places to eat on a regular basis.

Portland Food Scene

The best way to start experiencing the Portland food scene is to probably check out a food cart. Food cart pods aren’t hard to find and in many cases they will give you a good sampling of the unique flavors available to you. Don’t let the low tech and simple aesthetic of a food cart fool you. There is some seriously mind blowing and delicious options coming out of those little trailers that rivals the food your Grandmother used to make on the holidays!

7. Shop For Records

This one is a bit specific I realize. I totally get that not everyone is into collecting vinyl. In fact most people aren’t. However, for me personally digging through crates of used records and discovering new music is one of my greatest passions. The old idea of a record store where one can just hang out, listen to some tunes, and talk with like minded folk about your favorite music is a pretty rare experience in most places. In Portland however, it happens all the time.

Portland Record Store

There are a lot of great record stores in Portland. Far more than I could possible list right now. Some regularly have live music and carry a massive variety of published material. If you want to discover titles that are difficult to find anywhere else, including on-line, I would recommend hitting up Mississippi Records and Tender Loving Empire. Both double as their own independent record labels and feature a lot of local titles complete with listening stations for those on the hunt for new sounds.

8. Go On A Hike

Oregonians love the outdoors. Rain or shine, wet or dry, warm or cold, day hike or week long backpacking trip, Oregonians very much enjoy experiencing the adventures one can find when getting outside. Thankfully, from Portland you can experience just about any outdoor activity your heart desires in a relatively short distance. Head an hour west and you will hit the Pacific Ocean. Head an hour east and you can experience world class snow sports. Head south and you will find lush valley floors and grasslands. Just a little ways north you can even visit a volcano! Waterfalls, lush forests, wide open deserts, and even hot springs are all within easy reach of Portland.

Say the word “hike” to anyone in Portland and most people will immediately point to The Columbia River Gorge as the easiest place to go. There is good reason for that. It only takes about 45 minutes in the car to get to more hikes at a variety of skill levels than you could possibly accomplish in a lifetime.

9. Watch The Swifts

Every year in late August, one of Portland’s most spectacular natural events begins: Thousands of Vaux’s Swifts gather in the city as they prepare to migrate to Central America and Venezuela. Migrating swifts often use chimneys as roosts (places to sleep), and they are likely to return to the same roost year after year. One population has been returning to the Chapman neighborhood in Portland since the 1980s, and it is one of the largest known roosting sites of migrating Vaux’s Swifts.

Portland Swifts

Swift watching has become a popular activity on warm summer nights, and on many evenings, more than 2,000 people gather to watch these aerial acrobats.

10. Try The Beer!!

Portland takes its status as America’s number one beer destination very seriously. I mean VERY seriously. The last time I checked, Portland has more independent microbrews within the city limits than New York, Los Angeles, and even Berlin Germany! We like our beer and we take equal pride in creating staple beers like IPA’s, lagers, and stouts, along with more exotic sour beers and more. As if that wasn’t enough, spring and summer in Portland feature numerous festivals and outdoor events dedicated purely to the art and craft of beer.

Portland Beer Scene

If you are new to craft beer I recommend heading to the nearest microbrewery and ordering a sampling of their offerings. This will give you a great idea of the type of beer you might like to explore further. Typically a beer sampling of five or more varieties will run you about ten dollars and can be enjoyed with friends. It certainly doesn’t hurt that many of the cities microbrew establishments also serve some of the best food in town, so double win!

Andrew Kaiser

My name is Andrew Kaiser, welcome to my site! I have a passion for making images wherever and whenever I can. I seek to capture humanity and the world around me with a focus on the figure. Film, digital, pinhole, and instant photography are all fair game for me.


I grew up in the California Bay Area and started taking photography seriously in High School. I was one of the lucky few who had a chance to go to a high school with a working darkroom and a teacher who understood that making images was an art form – care and patience was a necessity in the image making process from start to finish.


Later in life I attended the University of California in Santa Cruz where I received a Bachelors Degree in the History of Art and Visual Culture. After having my fill of the California sunshine I packed up my life and moved to the Pacific Northwest. I quickly found the overcast skies, lush forests, cooler temperatures, and creative communities to be a perfect match for my work.


Over the years I have exhibited my photographs in several galleries and art shows including the Seattle Erotic Arts Festival and Cascade AIDS Project. I’ve published a few books and taught workshops up and down the west coast of the United States. Through this site I’m hoping to share my work and perhaps inspire others along the way.