Post Overview: A lifelong local shares the best things to do in Portland, Oregon.

Portland is my beloved hometown. I’ve lived here my entire adult life and have come to know the city like the back of my hand.

From the outside Portland is known for easy-going locals, a knock-out food scene and residents that grow chickens in backyards. All these things are true, but there’s so much more to daily life in Portland that makes the city so appealing for visitors and locals alike.

Indeed, after spending thirty years in Portland, I can confirm that the list of unique things to do in Portland, Oregon is never-ending.

In recent years the city has grown like a weed and visitors arrive in hordes to see for themselves what all the fuss is about. Time is precious, no need wasting it on tourist traps and mediocre restaurants — especially in a city like Portland.

That’s where I come in, allow me to share my personal list of the best things to do in Portland, Oregon from a local’s perspective. I hope you enjoy!

P.S. If you’re looking for a place to stay while visiting Portland, this is my favorite hotel (I recommend it to my own family and friends).

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Who am I and why should you trust me?

Don’t worry, I don’t offend easily and this is a fair question. As mentioned, I’m a lifelong Portland local. I grew up in the City of Roses and spent most of my weekends exploring the city and surrounding areas.

Portland saw me through all of my major life moments — from high school and college to my first real job to my venture into entrepreneurship (mercy).

I’ve celebrated milestones in various Portland restaurants and bars. I’ve seen the city fall into a slumber during COVID and slowly rise again – and through it all, I’ve loved every minute of my time here.

I’m also an avid reader and have done my fair share of learning about Portland’s history. I’ll be sharing some of the most fascinating facts and lessons below.

Note for you, dear reader: If anything in this post doesn’t make sense or if you have any questions let me know in the comments below. I want your time in Portland to be enjoyable and I’m here to help make that happen, so don’t hesitate to reach out. I love hearing from you!

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Best Things to Do Portland, Oregon

Portland in particular is a cheap enough place to live that you can still develop your passion – painting, writing, music. People seem less status-conscious. Even wealthy people buy second-hand clothes and look a little bit homeless.

Chuck Palahniuk, author of the award-winning novel Fight Club. 

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#26. Explore the Pearl District

Portland’s trendy Pearl District is best described as industrial chic. Towering high rises (with rent prices to match, mind you) have cropped up around beautiful red-brick buildings — two worlds blending together seamlessly.

This Portland neighborhood is popular among locals thanks to the plethora of independent boutiques, modern cafes, cozy bars and charming galleries. Originally home to factories and loading docks, the Pearl has recently reinvented itself and is eager to show off.

The warehouses have since been converted into airy light-filled condos and the cobblestone streets of yesterday lead the neighborhood into the future. Today the beloved Pearl District serves as a testament to the power of breathing new life into a (once) neglected area, to everyone’s benefit.

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#25. Stroll down Mississippi Avenue

When most people think of Portland’s quirkiness they probably envision the lively corridor that is Mississippi Avenue, which is why exploring this area is one of the best things to do in Portland.

Mississippi Avenue is lined with colorful storefronts and locals shops that cater to any whim a millennial might enjoy. There’s a beautiful plant nursery, awesome restaurants (try the burger at Bar Bar), food carts, fantastic breweries (some of the best in Portland!) and plenty of charming shops.

Check the roster at Mississippi Studios and try to grab tickets to a show — catching a live music performance is one of the best things to do in Portland and Mississippi Studios doesn’t disappoint.

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Things to Do on Mississippi Avenue

FOOD | Prost Marketplace: A food cart pod serving creative cuisine on Mississippi Ave. Regardless of what you choose to eat (Matt’s BBQ is my personal favorite), make sure to grab brews from Prost, the German brewery adjacent to the cart pod. This food pod has picnic tables, lighting and a tent to keep diners dry – come rain or shine.

FOOD | Stormbreaker Brewing: Stormbreaker is a crowd-favorite among local Portlanders for their hoppy IPAs, memorable ciders and great outdoor seating. Founded in 2013, this beloved Portland brewery now boasts two lively locations. Enjoy a cold glass of cider or an IPA over pub fare (the nachos are worth mention).

FOOD | ¿Por Qué No? Taqueria: ¿Por Qué No? Taqueria serves up the best tacos and guacamole in Portland, and the long lines prove it. Their margaritas also hit the spot, so if you’re craving great Mexican food during your 3 days in Portland, look no further.

Swing by during Happy Hour (Monday-Friday from 2:30-5pm) for $1 off sangria, margaritas and cocktails, or visit on Taco Tuesday when the taco menu is 10% off.

SHOP | Meadow: Salt, Chocolate and Bitters: A cute shop worth a visit even if you don’t plan to purchase anything. They have finely selected chocolates from all over the world in addition to massive salt blocks and unique wine.

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#24. Enjoy Tom McCall Waterfront Park

Tom McCall Waterfront Park is named after Oregon’s revered governor. The park swells with locals during lunch hour and it’s inevitable that you’ll be dodging bikers, walkers, skateboarders and young couples walking hand-in-hand.

One popular attraction along the waterfront is the Oregon Maritime Museum, this is a great stop for anyone with kids.

And if you’re looking for things to do in Portland on a Saturday, swing by the Portland Saturday Market where local merchants sell unique crafts, it’s a great place to pick up souvenirs!

Try to time your visit to the waterfront with the spring season because this is the best spot in Portland for cherry blossoms.

The 100 Akebono cherry trees that line the waterfront were gifted by the Japanese Grain Importers Association in 1990.

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#23. Find zen at the Portland Japanese Garden

Originally opened in 1967, the Portland Japanese Garden is regarded as one of the most authentic Japanese gardens in America. And when you visit for yourself you’ll quickly see why. The garden is perfectly manicured with a small pond, handful of waterfalls and moss-laden paths ripe for exploration.

Touring the garden offers a perfect zen-escape for anyone feeling overwhelmed with the plethora of things to do in Portland. Make sure to check out the cozy Umami Cafe for matcha or order any of the tea on the menu, it’s a great way to slow down for a few minutes and enjoy the day.

On a side note, my husband and I have visited Japan (we fell in love with the country) and can confirm that the Portland Japanese Garden is truly authentic. We felt like we were transported back to the tranquility and culture we so loved in Japan.

I can’t recommend this experience enough for first-time visitors looking for things to do in Portland, especially if you’re visiting during the fall months when the garden comes alive with exceptional fall color.

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#22. Enjoy OMSI After Dark

The Oregon Museum of Science & Industry (OMSI) is a Portland rainy day staple. Most lifelong locals have memories of spending drizzly weekends at OMSI or visiting during school field trips. It’s a great place to get your fill of fascinating science exhibits, especially when there’s rain in the forecast.

Indeed, those searching for the best indoor activities in Portland on a rainy day with kids, will find plenty to do at OMSI. But even if you don’t have kids you shouldn’t write off this gem. Rather, sign up for the fun OMSI After Dark experiences.

OMSI After Dark is a 21+ event that takes place the last Wednesday of the month (typically). Local vendors, scientists and artisans host creative science-themed workshops. Visitors can get drinks, watch shows or try a plethora of interesting demos.

What’s more, all the permanent exhibits are open during the event, which means you can explore at your heart’s content. Spending a day learning something new is one of the best ways to take advantage of a rainy day in Portland! Learn more here.

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#21. Explore Alberta Arts District

Whenever I have a spare weekend for exploring I seldom resist the gravitational pull that leads directly to Alberta Arts District because because this lively Portland neighborhood has it all.

From delicious food, tons of cute local shops, charming boutiques and some of the best murals the city has to offer. It’s a great area to explore for anyone curious to learn about the things locals do in Portland.

Swing by the Kennedy School to see what happens when you convert a school into a hang out spot for the neighborhood (the detention room was converted into a bar!).

Lest I forget, if you’re visiting Alberta Arts District during the summer months, makes sure to check out the Last Thursday Art Walk where local vendors, artists, performers and musicians share their craft along Northeast Alberta Street.

It’s a very fun way to spend a summer evening in Portland.

Where to eat + drink:

Proud Mary Coffee ($$): One of my top 5 favorite brunch spots in Portland. Proud Mary hails from Australia and chose to make Portland its first US destination – how lucky can one city be?

Pine State Biscuits ($): This is a Portland staple and graces most “top places to eat in Portland” lists. The Reggie is an easy crowd favorite and their plain biscuits are so good I sometimes sneak them in as snacks.

Bollywood Theater ($$): A super hip Indian restaurant with delicious fare. We visited with a group of friends for a birthday celebration and tried about 15 small plates – all were big hits! Plus, the atmosphere is great, especially for groups.

Great Notion Brewery ($ – $$) : We discovered this place through a close friend of ours that lives in Alberta and were very thankful for the recommendation. The smooth yet complex brews this brewery churns out are hard to describe, but they’re sensational.

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#20. Explore the mysterious Witch’s Castle and learn about its haunting past

You might be asking yourself what can be so haunting about an abandoned structure in the middle of a forest? Two stories converge at the center of this place, the story of an angry father accused of murder and the story of a love-stricken daughter paralleling Romeo and Juliet.

And this age-old tale of murder and haunt makes a visit to the Witch’s Castle all the more interesting.

Ask any Portlander and they will tell you that hiking to the Witch’s Castle feels like a rite of passage because it feels as much a part of the city as the the Keep Portland Weird motto, which is why you simply can’t miss it during your visit. It’s also a great short hike.

Further Reading: Visiting the Witch’s Castle in Portland, Oregon

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#19. Visit Pittock Mansion

Touring Pittock Mansion is one of the coolest things to do in Portland for history buffs. A stunning French Renaissance-style mansion sitting atop the West Hills and spanning 16,000 square feet. Pittock Mansion boasts 46 elaborate rooms and is open to the public for tours.

The tours are really cool because you can see the original furniture from the time period and learn more about the family that called it home (these folks were loaded). No expenses spared, the house was built so well that even the original elevator is operational to this day.

The Christmas season is especially remarkable because the mansion is decorated in the most elaborate manner with tons of Christmas trees.

If you’re pressed for time and decide not to tour the mansion, at least make sure to head to the overlook behind the mansion for unparalleled views of downtown Portland.

Pittock Mansion has the best viewpoint in Portland, believe me, I spent a month searching for the best views in Portland and this comes in at #1.

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#18. Take a photo with the Keep Portland Weird sign

The Keep Portland Weird sign has become synonymous with the city’s lifestyle and even feels like a call to action for some folks. You’ll see the slogan on bumper stickers, t-shirts, posters, you name it.

Everyone that comes to Portland heads to this mural for a reason, it’s an iconic thing to do in Portland! So you won’t want to miss it during your visit.

Apparently the motto was originally borrowed from Austin, Texas (how one “borrows” a motto is beyond be, but I digress). It was brought to Portland in 2003 by Music Millennium owner terry Currier with the intention of supporting local businesses.

Location: 22 SW 3rd Ave, Portland, OR 97204

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#17. Ride the iconic Portland Aerial Tram

In 2007 the City of Portland celebrated the opening of the Portland Aerial Tram to great fanfare from excited locals and hospital employees.

Originally built as a vital connection between the Oregon Health & Science University’s (OHSU) main campus on Marquam Hill and the south waterfront, the Tram is a creative solution to a problem that was difficult to solve for a while.

On a typical day, up to 20,000 people visit OHSU (the largest employer in Portland) so it was not uncommon for the hilly 2-lane road leading to the main campus to get severely congested, posing challenges for ambulances and never-ending headaches for the surrounding neighborhood.

Upon reviewing various options to help alleviate the demand on road infrastructure, the City and key stakeholders agreed to take on the momentous task of constructing a tram — joining a (very) short list of American cities with aerial trams.

The Tram was custom-designed in Switzerland and is held to strict Swiss aerial tramway standards.

I consider this a fun thing to do in Portland because the views are breathtaking, especially at sunset.

You’ll get sweeping views of the south waterfront with Mt. Hood (the third most climbed mountain in the world) looming in the background.

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#16. Stroll down NW 23rd Avenue

NW Portland is a pretty tree-lined residential neighborhood peppered with smalls shops and great restaurants. This is the neighborhood I’ve lived in the longest because of it’s charm, walk-ability and access to everything I need (grocery stores, entertainment and parks).

Whenever we show guests around our town, this usually ends up being one of their favorite things to do in Portland.

The best way to explore NW Portland is to wander through the neighborhood on foot. Stroll down 23^rd Avenue and check out the shops that line this popular shopping street, often called “trendy third.”

If you’re in the mood for a great happy hour deal, I highly recommend Life of Pie Pizza. And if you have an insatiable sweet tooth, Papa Hayden is non-negotiable. They serve the best cake in Portland.

Further Reading: Local’s Guide to NW Portland

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#15. Eat from a food cart

Chances are good that you’ve heard Portland called a foodie city and trust me when I tell you it lives up to the hype. My favorite thing about Portland’s food scene is that it lacks pretension, turns out you can have a great meal without a white table cloth, what a novel idea.

Nowhere is this more evident than at the various food cart pods throughout the city.

Food trucks aren’t just for tourists. Most of my coworkers eat from food trucks during lunch so you’ll be acting more like a local than a tourist with this activity.

Here’s a list of my favorite Portland food cart pods:

• Hawthorne Asylum
• Fifth Avenue Pod
• Third Avenue Pod
• Cartlandia
• Cartopia
• Prost Marketplace

Further Reading: My 10 Favorite Food Cart Pods in Portland

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#14. Get drinks at Departure rooftop bar

Imagine a warm summer night hanging out with a group of friends while enjoying drinks at a rooftop bar. If that sounds like your idea of fun (call me!), then Departure is the place for you.

Departure is located in the heart of downtown Portland (one block from Pioneer Courthouse Square, lovingly known as “Portland’s Living Room”). This is a great place to hang out and get some great views of Portland.

Another great restaurant with city views is Portland City Grill. The Big Pink Building is the tallest building in Portland and someone was clever enough to put a restaurant on the top floor – genius! Happy Hour is a good deal, I suggest arriving an hour before sunset because the place fills up quickly.

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#13. Have a pizza in the best pizza city in America

As you may have heard, Portland recently outranked New York City as the best pizza city in America. No easy feat, as you can imagine!

We could talk about how Portland, Oregon was recently rated the Best Pizza City in America. We could talk about the discernible eye-rolls and sardonic sighs evoked from resolute east coasters.

Or we we could talk about the tepid applause from Portland locals because the sensational headlines only confirmed what we already knew — the pizza in Portland was underrated for too long, and we meant to keep it that way.

Between the traditional New York style, artisanal wood-fired Neapolitan or the beloved deep-dish Chicago style, Portland can satisfy the needs of any ardent pizza lover. Sampling pizza is a must-do for foodies looking for the best things to do in Portland, Oregon.

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Here’s the top three Portland Pizzas I recommend:

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Apizza Scholls (for New York-style pizza)

Technicality aside, Apizza Scholls is a Portland institution. Founded in 2005, this beloved Portland pizzeria has been serving Portlanders for almost 20 years and doesn’t show signs of slowing anytime soon. The restaurant has two cozy dinning areas and neither are very large, which means snatching a table on a weekend evening is nothing short of a feat but well worth the effort.

If you’re one of the lucky few that snatches a reservation, the large pies are reward enough. Cooked in an electric oven with one mission: simple and fast. They don’t complicate the art of pizza making, the menu is perfectly curated with the proper toppings-to-crust ratio.

Clear standouts are the New York White (garlicky cheesy perfection) and the classic pepperoni (the pepperoni cups curl at the edges – mercy!). Whichever pizza you decide to order, make sure to start with the Caesar salad, it’s one of the best in Portland.

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Ken’s Artisan Pizza (for Neapolitan pizza)

Ken’s Artisan Pizza hails from Portland’s best baker, Ken Forkish, the two-time James Beard Award wining mastermind behind Ken’s Bakery in NW Portland. This iconic Portland pizzeria self promotes as Italian-inspired with an American accent.

The long-fermented sourdough/yeast blend creates generous airy bubbles within the soft crust. Pies are expertly charred in a trusty wood-fired oven immediately after being topped with locally sourced ingredients like hand-stretched cheese.

You can’t go wrong with a single item on the menu, but I’m partial to the Fennel Sausage and the Brooklyn (Mike’s Hot Honey steals the show). The Caesar Salad is non-negotiable and the cocktails are equally delicious.

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Ranch PDX (for deep-dish pizza)

Ask any Portlander about the best deep dish pizzas in Portland and the honest ones will mention Ranch PDX. The dishonest ones will try to keep it a secret.

Boasting four lively locations since opening in 2017, Ranch PDX specializes solely in deep-dish pizzas in Portland — making them the perfect example of mastering one thing. The hearty deep-dish pies coming out of the oven are guaranteed to impress even the most ardent food critic.

The menu isn’t overwhelming (the perks keep adding up), and everything on offer is great. I’m partial to the classic pepperoni and The #4 (heaping portions of spicy port sausage neighboring chilies and soothing ricotta).

Also worth mention, with a name like Ranch PDX, the restaurant is making a statement. Their homemade ranch is a perfect companion for the deep dish pie. Four locations:

• 916 NW 21st Avenue, Portland, OR 97209
• 2239 SE 11th Ave Portland, OR 97214
• 1760 NE Dekum Street, Portland, OR
• 12960 SE 162nd Ave. Suite 202 Happy Valley Oregon

Read the complete list: 15 Perfect Portland Pizzas (Ranked by Pizza Type)

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#12. “Howdily-doodily, neighborino!”

Few people know that the creator of The Simpsons, Matt Groening, grew up in Portland, Oregon. As such, you may notice that a lot of the streets in NW Portland seem familiar. The reason? A handful of Simpsons characters are named after Portland streets.

So if you’re looking for unique things to do in Portland, why not go on a self-guided tour and search for all the streets that the Simpsons characters are named after?

Further Reading: The Simpsons & the City of Portland

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#11. See the second largest copper statue in America

Sitting pretty at nearly 35 feet, the Portlandia Statue is the second largest copper statue in America — second only to the Statue of Liberty in New York City. The City of Portland commissioned a sculptor named Raymond Kaskey to create the sculpture after the figure on the Portland seal (fun fact, he modeled the statue’s face after his wife).

Kaskey completed sections of the statue near Washington D.C. and began shipping it to Portland (piece by piece) via boat. It was assembled in Portland and finally installed on the Portland Building in 1985.

You might ask yourself why such an iconic statue is not better known. Well, the sculptor guards the rights to the statue strictly and doesn’t allow photos of it to be used for commercial purposes, and threatens lawsuits when his request is not met.

However, the statue may look familiar to Portlandia fans because the show received permission to use the statue after hefty negotiations and an agreement not to use it in a “disparaging way.”

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#10. Go on a brew tour in the best beer city in America

Of all the things Portland is known for, perhaps the most notable is Portland’s beer scene. In fact, Portland is often rated as the best beer city in America. Our area of expertise? Craft beers and IPAs.

It’s almost impossible to be disappointed at most Portland breweries but there are some clear standouts you can’t afford to miss.

Breakside Brewing: From a local’s perspective, no brewery shines brighter than Breakside Brewery — largely thanks to the plethora of awards and accolades bestowed upon it. The prestigious awards span the gamut and there’s simply too many to list, but the Gold Medal at the Great American Beer Festival is worth mention.

Stormbreaker Brewing: Stormbreaker is a crowd-favorite among local Portlanders for their hoppy IPAs, memorable ciders and great outdoor seating. Founded in 2013, this beloved Portland brewery now boasts two lively locations. Enjoy a cold glass of cider or an IPA over pub fare (the nachos are worth mention).

Culmination Brewing: Culmination Brewing is on everyone’s lips for a reason, this brewery churns out some of the most innovative and perfectly executed brews in Portland. Opened in 2015, Culmination has focused on creating a relaxed and welcoming space for the community by way of great beers.

Ecliptic Brewing: Started by brewing icon behind some of the most well-known beers in the state, including Mirror Pond Pale Ale, success was all but guaranteed at this highly anticipated Portland brewery. The menu highlights local and seasonal ingredients and is re-imagined every six weeks. You can expect to find everything from cult-following brews (like the Starburst IPA, Capella Porter and Carina Peach Sour Ale) to creative experimental brews dependent on the season.

Migration Brewing: Founded in 2018, as a passion project of four friends, Migration Brewing is a staple in the Portland community. They’ve successfully created an inviting space for guests to linger over excellent brews and delicious pub fare. The IPAs are a crowd-favorite, but we’re partial to the hearty pilsner. Regardless of what you order, you won’t be disappointed, but seriously – don’t skip the food!

You’ll find a robust tap list of 20 beers, ranging from traditional brews like IPAs, ambers and stouts to more innovative sours and barrel-aged beers. You’re bound to find something impressive here.

You may enjoy: 15 EPIC Portland Breweries Guaranteed to Quench Your Thirst

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#9. Does Portland have the best coffee in the country? Judge for yourself

Portland consistently ranks as one of the top 3 best coffee cities in America (our neighbors Seattle and San Francisco are always in the mix, too).

And I can tell you from firsthand experience that Portlanders are downright spoiled with good coffee options.

It’s hard to accept a mediocre cup of joe when you live in a place like Portland which is why I highly recommend drinking as much coffee as you can while you’re visiting the city — and whatever you do, DON’T go to Starbucks (their coffee is subpar at best compared to Portland cafes).

In fact, one of my favorite things to do in Portland with out of town guests is to start every morning at a different cafe and have them rank them.

Best Coffee in Portland (According to Locals)

Stumptown Coffee at the Ace Hotel: We can’t talk about the best coffee in Portland without mentioning the original, Stumptown Coffee. Still considered the most iconic coffee shop in Portland, this gem has spread to several locations across the country. Swing by to see why locals maintain a steadfast devotion to Stumptown regardless of all the new cafes that have cropped up over the years.

Coava Coffee Roasters: Coava roasts its own beans, which are so well known that many Portland cafes choose to use them exclusively. Specializing in pour-overs and espresso, rather than latte art, this is the place to go if you want a great cup of coffee with a focus on the beans. The baristas are some of the friendliest I’ve come across and take great pride in sharing their knowledge of the day’s beans.

Spella Cafe: Originally started as a food cart before finding a more permanent home in a tiny hole-in-the-wall, Spella Cafe will transport you to Italy instantly. So if you like old-school cafes with charming European, this is the spot for you.

Spella Caffe has mastered the craft of coffee. The cappuccinos are airy and light and we’ve never had a bitter taste from the properly-roasted beans. Local’s Tip: Their affogato (ice cream with espresso) is the best in Portland.

Heart Coffee: Started by a married couple that began roasting beans out of their home, Heart Coffee has a cult following in Portland thanks to their delicious high-quality coffee and Instagram-worthy interiors.

You’ll find folks ardently consumed by laptop screens, coworkers discussing deadlines and excited out-of-towners with cell phones in hand. One thing is guaranteed, everyone will leave happy because even the simplest drink is bound to impress at this great Portland cafe.

Further Reading: 15 Charming Portland Cafes You Can’t Help But Love

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#8. Make a meal with produce from a local farmers market

Is there anything more Portland than local produce and supporting small business?

I don’t think so, and thankfully there’s plenty of quaint farmers markets peppered throughout the city combine the best of those two worlds.

If you’re looking for things to do in Portland during the weekend, swing by a farmers market Saturday or Sunday morning and pick up some fresh seasonal produce from local merchants.

Impress your family and friends by whipping up an interesting meal using a recipe from this award-winning cookbook (written by a Portland chef) and combining your meal with the perfect glass of wine, as recommended by this charming wine-pairing cookbook (written by two fabulous Portland locals).

Further Reading: The 10 Best Portland Cookbooks

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#7. Have a sunset picnic and take in some breathtaking city views

There’s no denying that Portland is a beautiful city. It doesn’t overwhelm with skyscrapers but instead offers a manageable downtown core and stunning views of looming mountains.

What better way to spend an evening that soaking in a breathtaking city skyline with a cozy picnic spread in front of you? There’s so many great Portland viewpoints to choose from but for first timers, I suggest either Mt. Tabor or Council Crest.

At 1,073 feet, Council Crest is the highest point in Portland, so you can bet the views from this park are glorious (especially during sunset). You’ll see Mt. St. Helens, Mt. Hood, Mt. Adams and even Mt. Rainier. So if I may offer some advice, head to the park for sunset as soon as you see a clear day in the forecast.

Mt. Tabor Park is yet another great spot to catch sunset. It’s hard to find a better spot for a summer picnic with friends. So pack your favorite picnic basket, or better yet, grab a pizza from Apizza Scholls (one of the best pizza places in Portland) and watch the sun fade over downtown Portland.

Regardless of where you catch sunset, this is one of the best things to do in Portland and an experience you won’t soon forget.

Further Reading: 10 EPIC Viewpoints in Portland

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#6. Take a hike in one of the largest urban forests in the country

Spanning more than 5,200 acres and offering 70+ blissful miles of trails, Portland’s beloved Forest Park is one of the largest urban forests in the country and it is ripe for exploration.

If you’re looking for active things to do in Portland, take a hike in Forest Park.

Forest Park swallows you up and makes you forget you’re anywhere near a city because of the towering old-trees, making it a great stop for anyone that gets overwhelmed by cities.

I especially like small portions of the Wildwood Trail (which connects Washington Park and Forest Park), the Ridge Trail and Lower MacLeay to Stone House (“Witch’s Castle”).

Further Reading: 25 Epic Hikes Near Portland

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#5. Bike around the most bike friendly city in America

With more than 350+ miles of bike lanes, Portland is considered the most bike-friendly city in the country.

I can tell you from first hand experience that biking around Portland is enjoyable, safe and a great way to explore the town (this is coming from someone that scares easily!).

In fact, biking is so popular in Portland that on average 5.3% of residents commute to work by bike, far exceeding the national average of .5%.

Hop on the local BIKETOWN bikes and take a lovely ride along the Willamette River to see exactly why Portland is called Bridge City. And whatever you do, don’t miss an opportunity to bike across the Tilikum Crossing bridge!

Take your bike for a spin at Waterfront Park, which is especially beautiful in the spring, if you want proof, read: Local’s Guide to Cherry Blossoms in Portland.

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#4. Explore the oldest public rose garden in the country

Portland is often referred to as the City of Roses because the local climate creates the perfect conditions for growing roses.

Nowhere is this more evident than at the exceptional Portland Rose Garden within Washington Park, which is usually in bloom from May to October.

Portland’s beloved rose garden is the largest and oldest rose garden in America. Home to an impressive 650+ varieties of roses and more than 10,000+ bushes, it’s easily one of the best free things to do in Portland.

The history of the rose garden is equally as fascinating. Originally started in 1915 by Jesse Currey, (an Oregon Journal editor and rose hobbyist), the rose garden was created in an effort to preserve roses susceptible to eradication during World War I.

You don’t have to be a rose-enthusiast to appreciate this beautiful garden. It’s no wonder why this is one of the most visited places in Portland.

Further Reading: Visiting the Portland Rose Garden (Local’s Guide)

Note: Washington Park is considered the crown jewel of Portland’s robust park system and is worth exploring during your visit to Portland. Located on the border of the NW neighborhood, this breathtaking park spans 400 acres and houses six important cultural institutions — the International Rose Test Garden, the Portland Japanese Garden, the Oregon Zoo, Hoyt Arboretum, Portland Children’s Museum and the World Forestry Center.

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#3. Enjoy a free jazz festival at Cathedral Park

If you’re looking for fun things to do in Portland during the summer I highly recommend enjoying some listening talented jazz musicians at the annual Cathedral Park Jazz Festival, held every summer over the span of a long weekend.

This popular festival is open to all ages and brings together a community of jazz lovers in an easy-going setting. Bring a picnic blanket or camping chairs and allow yourself to enjoy the pure bliss of music and nothing else.

The Cathedral Park Jazz Festival is one of the best free things to do in Portland during the summer.

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#2. Visit the smallest park in the world

In 1971, Guinness World Records confirmed what most Portlanders already knew — Mill Ends Park is the smallest park in the world. Clocking in at a mere two square feet, Mill Ends Park is officially recognized as the smallest park in the world. It wouldn’t Portland if it wasn’t weird, right?

Regardless, this little park is a beloved Portland treasure and visiting it is one of the quirkiest things to do in Portland.

And sure, this is a quick pop over best coupled with other more interesting things to do in Portland but I’d be remiss to leave this off the list. This is a photo opportunity with a world-record, who can pass that up?

Fun trivia: The tree was actually stolen once (in 2013) but promptly returned, presumably due to remorse.

Further Reading: 12 Stunning Parks in Portland, Oregon

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#1. Shop at the largest independent bookstore in the world

Rated by CNN as one of the coolest bookstores in the world, Powell’s Books, dubbed City of Books, is the largest independent bookstore in the world – selling both new and used titles for all to enjoy.

Home to more than one million new and used books, the store covers 4 floors. If that sounds overwhelming, grab a map before embarking on the adventure. Arrive early or be prepared for crowds, visiting Powell’s is by far one of the best things to do in Portland.

Fun fact: Pop into the Gold Room during your visit to see the rarest books in the store. The most expensive book at Powell’s is an 1814 copy of the Lewis & Clark Journal which includes Captain Lewis’ map safely tucked between the pages. The price? $350,000.

Read: Local’s Guide to Powell’s Books

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Bonus: Order a seasonal scoop from Salt & Straw

Salt & Straw has amassed a cult-like following since opening in 2011 and the steadfast devotion is justified — they churn out the best ice cream in Portland. Locally sourced seasonal ingredients take center stage and the innovative (albeit unusual) seasonal flavors warrant a sample or two.

Originally started in Northwest Portland and has since grown like a weed, currently boasting four Portland locations and expanding to six US cities.

There’s a reason this place is so popular, this is arguably the best ice cream in the state. What’s more, the creative seasonal flavors are practically guaranteed to impress. I’m partial to the honey-lavender flavor.

Make sure to sample the strangest sounding item on the menu (I once tried bone marrow ice cream and it was actually quite good).

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Portland Tourist Traps to Avoid

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#1. Voodoo Donuts

Voodoo is a tourist trap, there I said it. Revoke my residency if you must but don’t shoot the messenger. The famous pink boxes were once synonymous with Portland’s commitment to quirky things — like donuts topped with cereal (groundbreaking, I know).

But today? A sign of an overly-eager tourist.

Mind you, I completely understand that most first time visitors to Portland will inevitably visit Voodoo Donuts (hey, I probably would too). But brace yourself — this place has become a tourist trap. You’ll find (much) better donuts here, here and here.

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#2. The Portland Spirit

The Portland Spirit was founded in the early 1990’s and I’m sure most Portlanders have taken a ride one time or another. But the food is mediocre, the drinks overpriced, and the boats seem tired.

Overall, I don’t think folks partake in this experience more than once because it’s too expensive for what it is. Save your money and time.

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#3. Ice skating at Lloyd Center

Ask any Portlander and I’m sure they’ll regale you with a story of ice skating at Lloyd Center as a kid. It’s what a lot of us do!

The ice skating rink in Lloyd Center is perhaps most notable thanks to Tonya Harding, an Olympian from Portland that used to train here.

But today the mall just feels tired, even with the recent renovation. You can easily skip a visit to the Lloyd Center while visiting Portland.

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#4. Chinatown

I’ll get hate for this, I can already feel it but I’m just being real. Chinatown is not worth the trip unless you want to be blown away at the sight of homeless encampments.

I say this because most of our family and friends that stay with us choose to visit Chinatown (especially for the Lan Su Chinese Garden) and come home practically distraught.

I suggest avoiding this area, even though tons of folks claim it’s a must-see while you’re visiting Portland.

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#5. Shanghai Tunnels Tour

While creating this list on the best things to do in Portland I made sure to reach out to local family and friends for their recommendations to make sure the list was as robust as possible. One of my friends asked me to mention that the Shanghai Tunnels tour felt like a tourist trap and they’d suggest avoiding it.

Intrigued, I asked for clarification. At $15 per person, they felt the experience was overpriced for what it is. The tour lasts 1.5 hours and takes you past three staged rooms located under a bar. There’s little factual information shared and the whole tour provides little educational value. Hard pass.

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Best Day Trips from Portland

So you spent a few days exploring fun things to do in Portland Oregon and now want to get a better understanding of the incredible nature the Pacific Northwest is known for? I got you covered.

Here’s a rundown of the best day trips from Portland, Oregon.

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Drive out to the Columbia Gorge

In terms of best day trips from Portland, it doesn’t get better than a visit to the Columbia Gorge.

Few know that the Columbia River Gorge is America’s largest National Scenic Area. And once you drive through this stunning landscape it won’t take long for you to realize that the honor is well deserved.

The Columbia Gorge is a study in contrast. From alpine meadows and jaw-dropping waterfalls to desert landscapes and tepid rain forests, there’s something for everyone.

As any Portland local will tell you, you absolutely must take out of town visitors to see the glorious Columbia River Gorge. It’s popular for good reason!

Less than a one-hour drive from the city, the Columbia River Gorge makes for a great day trip from Portland even if you only have half a day to spare.

Things to do in the Columbia River Gorge:

• Visit Multnomah Falls, the tallest waterfall in Oregon. Tip: The parking lot fills up very quickly so make sure to come early. Also, don’t miss hiking to the overview bridge, it’s well worth the small effort.
• Hike Dog Mountain (super popular hike that comes alive with pops of yellow when the sunflowers are in full bloom (May-June). Permits required during weekends.

Bonus Points: Visit the Hood River Lavender Farm (Summer Months)

The lavender fields in France are known the world over for their stunning beauty and heavenly smell. But you know what? You don’t even need to buy a plane ticket to have an equally memorable experience in our own backyard.

Hood River Lavender Valley comes alive with pretty shades of deep purple during July and August for the enjoyment of visitors and bees.

Both flock to this area to take in the beauty of lavender growing at the feet of a charming old barn while Mt. Hood gracefully looms in the background.

You know what they say, a picture is worth a thousand words. Obviously, Hood River Lavender Farm needs to explanation — the picture speaks for itself. This is one of the most beautiful places in Oregon!

Read More: 10 Enchanting Oregon Lavender Farms Worth the Drive

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Take a road trip to the Oregon Coast

Nothing screams Pacific Northwest like the striking Oregon coastline. A scenic 1.5-hour drive from Portland will lead you directly to the salty sea. If you’re pressed for time, make Cannon Beach your top priority.

Cannon Beach is the most popular beach on the Oregon Coast, you may have seen photos of Haystack Rock before (it’s very famous). As such, this is a perfect day trip from Portland.

My childhood is freckled with memories of summer at the Oregon coast, so I’m definitely biased. It took my husband a few visits to fall under the coast’s spell, but as soon as he discovered crabbing and clamming – he was hooked!

Things to do at the Oregon Coast:

• Hike God’s Thumb
• Visit Haystack Rock
• Explore Ecola State Park
• See all 11 lighthouses in Oregon

Further Reading: 15+ Charming Oregon Coast Towns You Can’t Help But Love

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Go on a winery tour in the Willamette Valley

Everyone knows that Oregon is an outdoor enthusiasts dream. The drastic (and diverse) natural landscapes can keep anyone entertained for years with miles of hiking trails and sweeping vistas.

But what’s the point in hiking without a proper reward afterwards? Well, Oregon has you covered in that department as well — in fact, Oregon is the 4th most wine producing state in the country.

And of all the notable wine regions in Oregon, perhaps none is more famous than Willamette Valley because it is home to 500+ wineries.

Sitting at the same latitude as France’s notable wine regions, Willamette Valley is known for producing knock-out award-winning Pinot Noirs that can hold their own in worldwide competitions.

Sipping a chilled glass of Chardonnay in the summer (or robust glass of award winning red in fall) while overlooking rolling hills of healthy vines? Just name a time and I’ll be there.

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Hike in Bend, Oregon

I absolutely love exploring Bend, Oregon and always recommend it to out of town guests. I’ve written extensively about the incredible hiking trails in the area.

If you plan to visit this charming town make sure to read: 15 Best things to do in Bend, Oregon

P.S. My husband was commissioned to create a video on the Deschutes National Forest by Visit Bend. It took one full year and hiking 80%+ of the trails in Bend to create the video.

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Best time to visit Portland

By and large, Portland tends to have mild weather year round. The one season I would avoid is winter because the colder temperatures make exploring less enjoyable (although there’s plenty of cozy coffee shops to take cover in!).

To that end, the best time to visit Portland is between May and October. The weather is comfortable (even during summer because there’s practically no humidity) and chance of rainfall is minimal.

If you can, try to time your visit with the vibrant spring season so that you can experience the cherry blossoms in full bloom or the breathtaking fall season when the city is ablaze with deep shades of orange, red and yellow.

Personally, my favorite seasons in Portland are fall (September/October) and spring (April/May). For what it’s worth!

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Great (fancy) restaurants to add to your Portland Itinerary

If enjoying a meal at a fine dining restaurant is high on your list of things to do in Portland, Oregon then you are in for a treat.

Whatever the occasion you’re looking to celebrate, there’s no shortage of memorable Portland tasting menus to celebrate at. But listen, I don’t need to be the first to tell you that not all tasting menus are created equal. Indeed, there’s nothing worse than shelling out for a meal you’ve forgotten by the time you get to your car (or bike) and I don’t want that to happy to you.

Below is a list of my personal favorite tasting menus in Portland, based on firsthand experience.

Le Pigeon: Ask any Portlander about the best tasting menus in Portland and the honest ones will name Le Pigeon first, the dishonest ones will keep it a secret. Opened in 2006 by (then 25-year old) Chef Gabriel Rucker, Le Pigeon is credited for single-handedly putting Portland on the national culinary map. I’m not exaggerating.

Le Pigeon focuses on seasonal French-inspired cuisine using ingredients sourced from the bounty of the Pacific Northwest. Offering two exceptional 5-course tasting menus (one for vegetarians) in a relaxed setting, I recommend opting for the brilliant wine pairing to cap off your experience.

Jaqueline: One of the best seafood tasting menus in Portland is Jacqueline (a personal favorite of mine). This chic seafood-forward restaurant is dressed to impress and exudes a welcoming vibe. Between the quirky decor (shout-out to the Bill Murray portrait) and the knowledgeable staff, you’ll feel right at home.

The easy-going vibe is not to be misunderstood, the folks that run this joint take seafood very seriously. Every dish is thoughtfully prepared with ingredients scored the morning of, ensuring the meal is as fresh as possible. If you’re unsure what to order, the 8-course tasting menu can’t be beat. The portions are generous without overwhelming. Perfectly spaced, you can take in the intricate flavors of each respective dish and leave completely satisfied at the end of the meal.

Ava Genes: Fresh, farm to table Italian-inspired cuisine. The chef, Joshua McFadden authored a James Beard Award winning cookbook titled Six Seasons: A New Way with Vegetables. A book I cannot recommend enough, especially the mushroom recipes.

Coquine:  Coquine is an award-winning Portland restaurant best known for their toothsome farm-to-table French-inspired tasting menus. In fact, many seasoned Portland chefs turn to this very restaurant when they’re in need of a good meal and some inspiration.

Helmed by Katy Millard, a well-regarded chef that trained in multiple Michelin-starred French kitchens, Coquine was welcomed with open arms when it opened in 2015. The restaurant was named Restaurant of the Year by Eater Portland that same year.

Further Reading: 8 UNFORGETTABLE Portland Tasting Menus Worth the Splurge

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Portland Itinerary Tips: Getting around Portland

Biking is the number one way to get around Portland. In fact, Portland is rated the most bike-able city in America year after year. So grab a BIKETOWN bike to explore town.

Driving in the city is fairly easy (especially if you’re comfortable driving in cities) and parking is reasonable at $2/hour in the downtown metered area.

For longer stays, the City of Portland has 5 parking garages that charge the same rates as on-street parking ($2/hour or $13-$16 all day).

Public Transportation is easy to use and fairly inexpensive ($2.50 for two hours/$5 all day). In addition to the bus, Portland offers the MAX and Portland Streetcar.

Uber/Lyft/Taxi are operational in Portland and (based on personal experience) reasonably priced.

When driving in Portland, it’s important to know that pedestrians ALWAYS have the right of way — even if sidewalks are unmarked.

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Where to stay in Portland

I suggest staying in the downtown core during your long weekend in Portland because it’s well connected by public transportation. There’s plenty of hotels in the area, plus you’ll be close to great restaurants, bars and entertainment.

My two top centrally-located hotel recommendations in the downtown area are:

The Nines Hotel: Swanky special occasion hotel a stone’s throw from Pioneer Square. Whenever celebrities or athletes come to town, this is where they stay.

Hotel Woodlark: New to the scene but makes quite an appearance. The lobby of this cute boutique hotel is home to Good Coffee, making it easy to start your day right.

But honestly, it’s hard to go wrong with any of the charming Portland neighborhoods.

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Best things to do in Portland Oregon (Post Summary)

In sum, these are the best things to do in Portland!

1. Visit Powell’s Books
2. Visit the smallest park in the world
3. Attend a free jazz festival
4. Hike in Forest Park
5. Visit the Portland Rose Garden
6. Enjoy a picnic at sunset
7. Bike around Portland
8. Visit a farmers market
9. Sample coffee
10. Go on a brew tour
11. See the Portlandia statue
12. Go on a Simpsons tour
13. Get drinks at Departure Rooftop Bar
14. Eat from a food cart
15. Have pizza in the best pizza city in America
16. Visit Tom McCall Waterfront Park
17. Stroll down Northwest 23rd Avenue
18. Explore the Alberta Arts District
19. Ride the Portland Aerial Tram
20. Take a photo with the Keep Portland Weird sign
21. Visit Pittock Mansion
22. Explore the Witch’s Castle
23. Go to Salt & Straw for ice cream
24. Stroll down Mississippi Avenue
25. Visit the Portland Japanese Garden

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Map of the best things to do in Portland

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Love Portland? Here’s some articles you may find interesting

• 20 HONEST Pros & Cons of Living in Portland
• 25+ EPIC Things to Do in Portland (+4 Tourist Traps to Avoid)
• 12 Stunning Parks in Portland, Oregon
• 20 Interesting Facts About Portland You Probably Don’t Know
• 10 Epic Portland Viewpoints to Check Off Your List
• 10 Adventurous Day Trips from Portland
• 30 Weird, Free & Cheap Things to Do in Portland
• Let’s Talk: Portland, Oregon Vs. Portland, Maine

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And there you have it my friends. hope you enjoyed the post about the best things to do in Portland, please don’t hesitate to reach out with questions and comments!

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Until next time,

Antonina

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