Japanese Gardens Portland, Oregon by Wandering Wheatleys

A Local’s Guide to the Best Kept Secrets of Portland, Oregon

Most people who actually grew up in Portland, and weren’t just lured here from California by the promise of cheap housing, will tell you that the city just isn’t what it used to be. They’ll reminisce about bars that used to be cool until the hipsters took over, about Portland neighborhoods that were affordable before they were gentrified, and delicious restaurants where you used to be able to walk right in and get a table.

Well, all of it is true, but that doesn’t mean that Portland isn’t still awesome.

I grew up in a house that was built by my great grandfather, Axel Anderson, back in the early 1900s. It’s in North Portland, on Sumner street, just a block and a half from the Adidas campus.

But, at the time that I grew up there, it was one of the least desirable neighborhoods in the city. Where Adidas sits now was actually Kaiser Hospital, and it was sliding down a hill. I couldn’t convince my friends to come for a sleepover at my house. My mom had to write letters to get me into the public schools in the more upscale neighborhoods further east.

So yeah, Portland has changed a lot. And housing prices have gotten significantly more expensive. But that’s because Portland has continued to become a more desirable place to live. And with that has come more delicious restaurants, better breweries, and larger weekend markets. It is now actually considered an appealing travel destination (but don’t worry, there are still plenty of weird things to do in Portland).

So, if you are one of the many others planning a big move to the west coast or even just a visit, check out 7 of the best things to do in Portland from a local expert!

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

Where to Stay in Portland

Portland has some cool boutique hotels, so if you’re coming to the City of Roses, make sure you check out these 12 cool hotels in Portland. On the other hand, if you want to really stay local, then check out some of these cool Airbnbs in Portland.

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What to Pack for Portland

Check out our list of packing essentials for your trip to Portland here!

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Portland Travel Tips from a Local: 7 of my Favorite Things!

1. Have a Long, Boozy Brunch

The Best Things to do in Portland, Oregon: Where to Eat in Portland: Brunch in Portland, Oregon by Wandering Wheatleys
Brunch options abound in Portland, Oregon

If you wake up on a Saturday or Sunday around 10 am, starving, maybe even slightly hungover, and want to grab a bite to eat, you must first ask yourself how long you are willing to wait.

If you are a 10 on a hunger scale of 1-10, you should probably head to the grocery store instead of a restaurant and get yourself some cereal. Because depending on the popularity scale of the restaurant you choose, you could be waiting upwards of 2 hours for a table. Even breakfast food trucks generally have an hour-long wait for their “fast” food.

On weekends, starting at 9 am, locals and tourists alike descend on the popular brunch spots around the city to create their own Bloody Mary bar concoctions, or sip bottomless mimosas while waiting for their fancy pancakes to arrive.

A few of our favorite Portland brunch spots:

  • Gravy – located in North Portland on the hip, but still quaint Mississippi Street, you’ll probably have a difficult time spotting the sign for Gravy, but will most definitely see the hordes of hungry people waiting outside. Known for their delicious gravy options (shocker, I know) and their creme brulee oatmeal, this is arguably the most popular brunch spot in Portland. Go either really early or near closing time for the shortest line.
  • Radio Room – offering a build-your-own Bloody Mary bar with over 80 hot sauce options, what more could you ask for? They also have delicious classic brunch options, cozy fire pits, and a fun atmosphere. There’s rarely a wait for a table.
  • Genies Cafe – located on SE Division, Genies resembles an old school diner. They use local cage free eggs and farm raised meats in their delicious traditional breakfast dishes. There’s usually a wait, but you can nab one of the best Bloody Marys in town at the bar to keep yourself entertained.
  • Screen Door – offering Southern home cooking, Screen Door is one of the most popular restaurants in Portland both for brunch AND for dinner (it’s rare to do both so phenomenally). Don’t even think about not ordering the fried chicken and waffles, you’ll regret it. You’ll definitely be in for a wait, and the line starts even before they open.
  • Salty’s – this is a more upscale (aka expensive) brunch dining experience, but it’s worth every penny. The massive buffet has everything from crab legs to a chocolate fondue fountain and everything in-between. Unlimited mimosas and a create-your-own Bloody Mary bar are also on the menu… (be sure to make a reservation!)

Not in the mood for brunch? Check out this Portland Food Guide for some more great dining recommendations!

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2. Go on an Urban Walking or Biking Tour

The Best Things to do in Portland, Oregon: Take a Walking Tour of Portland: Tilikum Crossing in Portland, Oregon by Wandering Wheatleys
Portland’s Newest Bridge – The Tilikum Crossing

Portland prides itself on being incredibly pedestrian-friendly. Its newest landmark is the no-cars-allowed “bridge of the people” called the Tilikum Crossing.

Pedestrians ALWAYS have the right-of-way in Portland, so if you find yourself behind the wheel be sure to exercise caution. Driving is actually one of the least desirable things to do in the city as the bike lanes and MAX lines have essentially taken over the streets. Ditch the 4 wheels and opt for either a set of two or your own two feet, for an urban biking or walking tour.

The downtown waterfront is a perfect place for Willamette River views and offers the most interesting people-watching around. A popular spot for joggers, business people taking a lunchtime stroll, and homeless kids doing drug deals – you’ll find all walks of life on the southwest waterfront.

Cross any one of the numerous bridges to the east side of the river, which is far less populated, to make your trip a loop. You’ll pass by the Oregon Museum of Science and Industry (OMSI), which is one of the best things to do in Portland with kids. Stop for a coffee at one of the cute restaurants popping up on the up-and-coming south waterfront area before making your way back to the hustle and bustle of the city.

After your tour of the waterfront, head west on Broadway street toward the Pearl District. Take a right on 10th street to pop into Powell’s, the famous and massive used bookstore. After checking out the cute little shops of the Pearl, keep heading west to NW 23rd street for more quaint shops and delectable restaurants.

Portland also has some amazing parks within the city limits. Be sure to check out:

  • International Rose Test Garden – take a stroll along the paved trail through the garden to marvel at the hundreds of rose varietals being tended to with loving care. Don’t forget to stop every now again to smell the roses!
  • Japanese Gardens – just across the road from the Rose Garden, you’ll find the tranquil Japanese Gardens. It’s the perfect place to sit in the shade by a bubbling fountain to ponder the meaning of life.
The Best Things to do in Portland, Oregon: Take a Walking Tour of Portland: Japanese Gardens in Portland, Oregon by Wandering Wheatleys
  • Forest Park – not many large cities offer massive parks smack dab in the city center, complete with a 40-mile loop system catering to pedestrians. Try our favorite hike – start at the Lower Macleay Park Trailhead and end at the Pittock Mansion for epic city views (and a tour of the mansion if you’re up for it).
The Best Things to do in Portland, Oregon: Take a Walking Tour of Portland: Light Rays in Forest Park, Portland, Oregon by Wandering Wheatleys
Light Rays in Forest Park
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3. Take a Drive Through the Columbia River Gorge

The Columbia River creates a natural border between Oregon and Washington. If you don’t have a car, you’ll need to rent one for this. Start cruising up I-84 towards Multnomah Falls. Just the view of the river from your car window is absolutely breathtaking.

The Best Things to do in Portland, Oregon: Drive Through the Columbia River Gorge: Punchbowl Falls in the Columbia River Gorge, Oregon by Wandering Wheatleys

A few of our favorite hikes in the gorge:

  • Latourell Falls – More of a short jaunt than a hike, Latourell Falls is just a 5-minute walk from the small parking lot on the side of the Historic Columba River Gorge Highway. This 224-foot waterfall drops in front of a black basalt cliff covered in bright greenish-yellow moss. It makes for a stunning setting and you can walk right up to the base of the falls if you don’t mind getting absolutely soaked! And if you’re up for it, there is a 2.4-mile loop that will take you up to the second tier of the waterfall.
  • Multnomah-Wahkeena Loop Hike – This moderate, 5-mile hike begins and ends at Multnomah Falls (a must-see in Oregon!) that gets you out of the crowds and into nature. You’ll pass by 8 waterfalls along this beautiful hike. It’s where we take our out-of-town friends!
  • Beacon Rock – This short (1.8-mile round-trip), but steep hike, on the Washington side of the gorge is an easy way to get epic views without too much time or effort. It’s paved and there are stairs that climb up the steepest parts, so it’s okay for the whole family.
The Best Things to do in Portland, Oregon: Drive Through the Columbia River Gorge: Views from Angel's Rest, Columbia River Gorge, Oregon by Wandering Wheatleys
Views from Angel’s Rest
  • Angels Rest – This moderate, 4.8 miles out-and-back hike offers flora and fauna along the well-beaten trail and a spectacular viewpoint at the end.
  • Dog Mountain – Another extremely popular hike in Washington state. The best time to do this moderate 6.9 mile hike is when the wildflowers are blooming in the spring. Check the wildflower report before you go.
  • Munra Point – This is a very strenuous 6-mile hike and not recommended for little ones. The last half mile or so is a steep uphill scramble to the lookout. You’ll be sweating like crazy once you reach the top, and then you’ll need to walk across a narrow trail with drop-offs on each side to the lookout point. Once you do, you’ll be rewarded with epic views of the gorge below.
The Best Things to do in Portland, Oregon: Drive Through the Columbia River Gorge: Munra Point in the Columbia River Gorge, Oregon by Wandering Wheatleys
Narrow trail to the summit of Munra Point
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4. Shop Local

I’ll start with this little gem – did you know that Oregon doesn’t have sales tax? Yep, that’s right, the price you see is the price you pay. Folks in bordering states often make the trip for large purchases to save themselves heaps of cash. So be sure to stock up on the goods while you’re in town!

Portland is filled to the brim with darling and unique shops featuring locally made goods. You’ll find all kinds of different shops in every little neighborhood of Portland. There are more upscale shops and art galleries in the Pearl and NW 23rd area, and funky clothing and accessory shops along Alberta, Mississippi, and Williams across the river.

A few of our favorite Portland shops:

Portland is also known for artisan and farmer’s markets all over town. There are three big markets that happen monthly, so depending on the timing of your visit, you should attempt to hit at least one!

A few of our favorite Portland markets:

  • Alberta Street Fair – takes place on the last Thursday of every month (except in the cold winter months). It’s an eclectic mix of street performers, live music, artwork, and outdoor cafes perfect for watching the spectacle of misfits wander past.
  • First Thursday – takes place on the first Thursday of every month (except in the cold winter months). It’s a classy affair with art galleries touting wine tastes and snacks and a few streets taken over by local artisans selling their wares.
  • Saturday Market – a little confusing, but this market is actually open on Saturdays AND Sundays. It’s the largest one in Portland – consuming a giant area along Naito Parkway on the waterfront. You can spend hours wandering through the maze of artisan shops. They also offer a large selection of food trucks and live music on the main stage.

5. Imbibe

The Best Things to do in Portland, Oregon: Imbibe: Things To Do in Portland, Oregon: Craft Beer & Breweries

Fun fact about Portland – it has more strip clubs per capita and more microbreweries than anywhere else in the world!  The booming craft beer scene was actually one of the things that originally put Portland on the map as an up-and-coming travel destination (perhaps the number of strip clubs had something to do with it as well).

It rains approximately 100 days of the year in Portland so, of course, one of the best things to do in Portland in the rain is head to the bar. But with so many options, finding your day-drinking destination can be a paralyzing decision. We’ve tried nearly all of them (for research purposes of course), so you don’t have to.

A few of our favorite Portland breweries:

  • 10 Barrel Brewing – this would likely be disputed by many Oregonians because 10 Barrel was once a small brewery and has since been purchased by Anheuser-Busch (boooo big corporations!). But the beer is tasty and their rooftop patio is one of our favorite spots to spend a sunny Saturday afternoon. Keep in mind that if you want an actual table, you would have to wait several hours. Opt for standing room only space and eat dinner elsewhere.
  • Great Notion Brewing – if you like sours, this brewery is a must! Try the Blueberry Muffin beer, it’s my favorite sour maybe of all time. Also the onsite taco joint is amazing!
  • Hopworks Urban Brewery (HUB) – sustainability and community involvement are high on the list of priorities at this local hot spot. Check out their Williams Ave location during happy hour!
  • Breakside Brewery – their NW Portland location has a huge and lively tasting room, perfect for meeting new friends! Plus they offer big portions of pub classics.
  • Von Ebert Brewing – located in the Pearl District, they pride themselves as being an independent craft beer brewery focusing on quality over quantity. Plus, their menu has a little bit for everybody.

A few of our favorite Portland bars:

  • The Alibi – a Portland institution. It’s a tiki-themed karaoke bar that is always busy on Friday and Saturday nights. If you actually want to sing karaoke, you’ll need to get your request in before 9 pm or toss the DJ some cash.
  • Teardrop Lounge – enjoy one, or a few, of the many original creations and beautiful cocktails made at their curved island bar.
  • Uno Mas – this is the gathering place for Timbers fans before and after games due to it’s delicious margaritas and close proximity to the stadium. If you can’t get tickets to a game – no fear! Hang at Uno Mas as they’ve got plenty of televisions and $1 taco specials.
  • Spirit of 77 – great space and an awesome local draft list with amazing happy hour specials. Plus, this is the perfect sports bar to catch a game!
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6. Eat at a Food Truck

I’d like to think that the food truck scene originated in Portland. It didn’t. According to The New York Times Magazine, the first food truck appeared in 1872 in Rhode Island when a man cut windows into a small covered wagon and sold sandwiches and coffee to businessmen working late. They really took off in LA in 2008, but Portland has taken the craze and run with it. We even have food trucks in our International Airport (which is one of the best airports in the world, by the way).

You’ll see food trucks all over the place in Portland. They have taken over several full downtown city blocks. You can find everything from cheesesteak sandwiches to gyros to burritos to curries and everything else your heart could desire. You’ve only got so much stomach space, so stick to our faves to ensure you try the best the city has to offer.

The Best Things to do in Portland, Oregon: Eat at a Food Truck: Gourmet S'Mores Food Cart in Portland, Oregon by Wandering Wheatleys
A Food Cart for Every Taste

A few of our favorite Portland food trucks:

  • 1927 S’mores– who doesn’t love a s’more? What about gourmet s’mores? This company makes handcrafted, gourmet s’mores that are just delicioius. From honey graham crakers, vanilla marshmallow, fudge, caramel, mocha, or even an expresso marshmallow…your sweet tooth will be very happy!
  • Potato Champion – if you like poutine fries, you will go gaga over this place. It’s perfect for a late night snack after hitting the bar scene around town.
  • Koi Fusion – love Mexican food? Love Korean food? Why not mix ’em! Koi Fusion has been around for a long time and have a ton of locations, but keep in mind that if food trucks aren’t keeping their menu and their food on-point, they don’t last long. So staying power means they’re doing something right. Try their take on the classic cheesesteak with Bolgogi beef and Kimchi!

7. Catch a Beer and a Flick

Movie prices have gotten a wee bit out of control these days. Luckily, Portland has a fantastic second-run movie theater scene. The movies they show have already been out for a few months and the theaters aren’t as posh, but they are generally half the price.

They also sell reasonably priced beer, wine, and snacks so you can have a fun outing with the family without breaking the bank. Sometimes you can even catch a cult classic movie screening (like Rocky Horror Picture Show) where fans dress up and shout out their favorite lines, which is wildly entertaining.

A few of our favorite Portland second-run theaters:

And lastly, if you have time… check out a Timbers soccer game, eat a donut (at Blue Star if you are looking for an amazing selection of tasty deliciousness, or Voodoo if you want to wait in line for an hour). There are so many things to do in Portland. Help us to KEEP PORTLAND WEIRD!!!

We hope you have a blast visiting Portland, Oregon!

Heading to Portland? Check out our favorite books!


Favorite things to do in Portland, Oregon by Wandering Wheatleys

About the Author:

  • Valerie Wheatley

    Val grew up in Portland, Oregon but moved to Oahu on a whim back in 2013. She sold her house and all of her belongings and bought a one-way ticket. Since then she’s taken two around-the-world trips and has visited 60-ish countries while living out of a duffel bag.

    Val started documenting the Wandering Wheatleys travels back in 2013 as a way to update friends and family about her whereabouts and to relay humorous daily interactions. The only readers were her mom and her mother-in-law but that didn’t stop her!

    These days you’ll find Val dreaming up future trips, creating new travel content, managing a team of amazing travel enthusiasts, and chasing around her two adorable but naughty kids.

16 thoughts on “A Local’s Guide to the Best Kept Secrets of Portland, Oregon”

  1. Great summary! Portland is on my list, and I’d definitely like to see the city then use it as a base to explore the hiking trails. The scenery looks epic!

  2. Jenn and Ed Coleman

    The Alberta Market seems amazing. There is a Feng Sui about periodic events. Once moth, excluding winter, seems like it happens enough to be well practiced and infrequent enough to retain an air of mystery and excitement.

    1. Yes, that particular market is pretty eclectic. Last time we went there were fire dancers and lots of strange costumes, lol. It’s perfect for people-watching!

  3. The more time we spend Blogging, the more we want to go to the US. You made me want to go to Portland now as well 😀 I’m so inreagued to see all the Microbreweries (for scientific reasons of course) and eat me through all the Food trucks (for biologic reasons)! Especially the Cheesus … OMG, I Need to try him! I feel like Rick and his quest for the Szechuan Sauce 😀 Thank you for this cool article!

    1. Ha! Sounds like you use the same excuses we do to eat and drink all the things! We also have world-renowned donuts (in case you need another reason to visit…)

  4. Portland is definitely a must-see for us! We love seeking out the booze scene in different destinations, so the breweries there are calling our name! But you got me even more intrigued with the brunches! I think we would have to check out Genies and Salty’s for sure!!

    1. Yeah! I hope you make it over for a visit soon! Brewfest happens one weekend every summer and might be the perfect time for your visit!

  5. forever roaming the world

    I have Portland on my list of places to visit when I go on my USA roadtrip – I’ve bookmarked this page for future reference. I would love to do a trip through the gorge it looks amazing 😀

  6. Traveling Well For Less

    What a great list of brunch places. I can’t wait to check them out. The Tilikum Crossing bridge looks cool. Love the downtown food trucks.

  7. Yes, well, it seems that every city in the world is changing in the same pace and manner. Gentrification has its good and bad side. But it’s lovely that you can still enjoy your town, that’s important, right! And why wouldn’t you when you have that beautiful gorge nearby and the Munra Point, that is absolutely stunning! 🙂

    1. Agreed on all points! And yes, with beaches, deserts, mountains, and waterfalls nearby you really can’t beat the location!

  8. Great detailed guide you have there! I’ve friends who went to school there and it sounded a beautiful town! I’d love to try those brunch options you mentioned. The little gems and markets you mentioned also sound really interesting. Love exploring little shops!!

  9. Great guide to Portland! We’ve been a few times but haven’t touched on many of the places and spaces you’ve mentioned. Though Powell’s and PokPok are always top of mind. Now we have a perfect excuse to return and do more exploration with your tips – thanks!

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