10 Cool Things to Do in Portland, Oregon

Portland, Oregon, is one of the coolest cities in the country thanks to its seemingly endless number of great bars, breweries, restaurants, and other local small businesses that give Portland its unique, slightly quirky (okay, sometimes VERY quirky) character. In fact, when you start to think about the best things to do in Portland, it will quickly become apparent that, unlike most cities in the US, there isn’t really a major tourist attraction in the traditional sense, like the Space Needle in Seattle or the Bean in Chicago. 

Instead, Portland is a city best experienced slowly, with an emphasis on exploring the small businesses that make the city special and unique. From vegan buffets to plant-based dog treats and artisanal donuts, if you’re searching for something unique and slightly niche, chances are that you can find it in Portland.

portland oregan sign

10 Things to do in Portland

But wait, there’s more! Just outside the city limits, you’ll find a selection of stunning natural beauty that puts Oregon near the top of the list of the most beautiful states in the union. From the rugged Oregon coast, just an hour or so west of Portland, to the stunning waterfalls of the Columbia River Gorge, just a half hour east of the city, there’s plenty of unique, natural beauty to be experienced within a short drive of the city center. 

Here are the best things to do in Portland, Oregon, whether you’re a foodie, outdoor enthusiast, or just looking for a nice, relaxing weekend getaway

Meander the Shelves at Powell’s Books

In a city chock full of small businesses ranging from food carts to plant stores, Powell’s Books is among the most famous. It’s the largest independent bookstore in the world, and you could spend hours wandering the aisles, discovering your next great read, and ending up buying WAY too many books to fit into your suitcase for the flight home. 

Hit one of Portland’s Outdoor Markets on Saturdays

Saturdays are an amazing day to be in Portland because there are two outdoor markets that take place in the vicinity of downtown that only happen on Saturdays. 

First is the PSU Farmers Market, which brings a staggering selection of farm-fresh produce and small businesses to a huge open area just south of downtown. This is the best farmers market in the city, and is a must-visit for foodies in Portland. 

Second is the Portland Saturday Market, which takes place along the river and is more arts and crafts focused, with local artisans selling their handmade goods at stalls along the river under the Burnside Bridge. 

Eat at a Food Cart

Portland is known for its food cart culture, and across the city, you’ll find collections of food carts – sometimes trailers, sometimes full-on trucks – circled around a collection of firepits and seating where locals are devouring a relatively affordable, delicious meal. 

There are a couple of pods that stand out for their collection of carts and atmosphere. The first is the Prost! Marketplace on Mississippi Avenue in North Portland, where you’ll find Matt’s BBQ Tacos and DesiPDX. Two others to check out are Cartopia and Hawthorne Asylum, which are a few blocks away from each other in Southeast Portland. 

In Downtown Portland, you’ll likely wander past a gaggle of food carts at some point – the most popular is the 5th Avenue Food Cart Pod (here on Google Maps) and the ones at Pioneer Courthouse Square

Explore Portland’s Green Spaces

In addition to donuts and food carts, Portland is also known for its parks and urban green spaces. 

The most famous is massive Forest Park, which is home to endless miles of hiking trails (try the Ridge Trail for amazing views of the St. Johns Bridge and a nice walk through the forest). The Wildwood Trail snakes its way through the park, covering nearly 30 miles from one end to the other. 

Washington Park is equally worth exploring, and it has four major attractions. The Hoyt Arboretum is a great place to do a short hike that features a variety of different plant species, including redwoods. The Portland International Rose Garden is home to 10,000 roses, and across the street you’ll find the tranquil grounds of the Japanese Garden. In the southwest corner, you’ll find the Oregon Zoo, which is a good place to take kids (and adult animal lovers too) and is the best zoo in the state of Oregon. 

On the east side of the river, Mt. Tabor and Powell Butte are great hiking destinations within Portland’s city limits. 

Experience the Waterfalls in the Columbia River Gorge

waterfall in portland

Just outside the city, you’ll find a collection of incredible, towering waterfalls that are a staple of any trip to Oregon. 

The Columbia River Gorge, which for the purposes of this guide runs from the Pacific Ocean to Hood River (though technically it continues east from there), is home to a bunch of incredible hikes, impressive waterfalls, and sweeping views that will have you saying “wait, this is only thirty minutes from downtown Portland?”

Here’s how to spend a perfect day in the Columbia River Gorge. 

Start your day with a scenic drive on the Historic Columbia River Highway, stopping at the Portland Women’s Forum State Scenic Viewpoint and the Vista House for two of the best views of the Gorge you’ll find anywhere. 

Stop and do the quick hike up to Latourell Falls to see both the upper and lower falls, which come thundering down from nearly 250 feet above. 

Cap off your morning of waterfalls with the queen of them all – Multnomah Falls. This is the tallest waterfall in Oregon at a staggering 620 feet tall, split between two tiers. There’s a nice bridge where you get an up-close-and-personal view of the falls. Get there early – parking is a nightmare. It might be worth heading here first to avoid dealing with parking. 

If you’re looking to add another hike to your itinerary, look at either Angels Rest, which takes you up to a rocky outcropping with a sweeping view up and down the Columbia River Gorge, or Dry Creek Falls, which is a much less crowded alternative that ends at yet another amazing waterfall. 

Smell the Roses at the Portland International Rose Test Garden

On a hill above downtown Portland, with a fantastic view of nearby Mount Hood and the Portland skyline, you’ll find the International Rose Test Garden. It is home to 10,000 different roses, and blooms in the spring and early summer, featuring roses of all different colors at their peak beauty. 

It’s also completely free, tucked inside Washington Park. 

Across the road is the Japanese Garden, which is not free, but is equally beautiful and serene. 

Eat a Donut (or Seven)

donuts

Somehow, Portland has become a mecca for donuts. From cheap to boutique, the donut scene in Portland is unmatched. 

Everyone and their mother heads straight to Voodoo Donuts, and it’s cool for the unique options, but at the end of the day, the donuts are strictly okay. Plus, you’ll spend way too much time waiting in line for said donuts.

Instead, head to Blue Star Donuts or NOLA Donuts for relatively expensive but insanely delicious donuts, or to Pip’s Original Donuts and Chai for fried-to-order donut holes (and some great, unique chai tea offerings, too) 

If you really want to get deep into Portland’s donut scene, you should take the Underground Donut Tour, where you’ll go with a local guide to a bunch of different spots (including some of the ones mentioned above) and sample the best donuts that Portland has to offer. 

Catch a Portland Timbers Game

If you’re a soccer fan and you happen to be in town when the Portland Timbers are playing a home game, then you should do your best to get tickets. Especially if they’re playing their Pacific Northwest rivals, the Seattle Sounders.

The atmosphere at Providence Park, home of the Timbers, is raucous and features a man wielding a chainsaw cutting off tree rounds every time the Timbers score. It’s one of the best soccer atmospheres in the country, and shouldn’t be missed by soccer fans of all ages. 

Explore the Neighborhoods East of the Willamette

While downtown Portland is home to many of the main tourist attractions in Portland – to the extent there are any “tourist attractions” in Portland – the more residential neighborhoods on Portland’s east side are where the magic happens. 

This is where you’ll find the vast majority of Portland’s best bars and restaurants, where real estate prices are a little bit cheaper, and Portland’s ever-creative restaurateurs, brewers, and other creatives can take more risks. 

On the northern end, Mississippi Avenue (don’t miss Pistil’s Plant Nursery and Meadow, a salt, chocolate, and bitters boutique) and Alberta Street (Proud Mary serves up some truly amazing coffee) are the two best stretches if you’re looking for places to eat, drink, and shop.

On the southern end, Hawthorne Blvd (Portland Cider Co and Fried Egg I’m In Love are two highlights here) and Division Street (Bollywood Theater for amazing Indian food and Salt & Straw for the best artisanal ice cream in Portland) are the cream of the crop, and foodies should make sure to walk both for a selection of Portland’s best eats. 

Hike to Pittock Mansion (and the Witch’s Castle)

If you’re looking for a nice hike in Portland to add to your itinerary, the hike from Lower Macleay Park up to Pittock Mansion is probably the best option. Pittock Mansion was built by one of the early investors and real estate moguls in Portland, and it has commanding views of the city’s skyline from its perch high up on a hill above the downtown area. 

The hike starts with a lovely stroll through the woods, following a creek past the Witch’s Castle, a creepy abandoned building covered in graffiti in the middle of the woods. You’ll cross the creek and start climbing a series of switchbacks to the top of the hill, where you’ll find Pittock Mansion. 

If you don’t have a car, you can do this hike one-way by taking a Lyft (or other rideshare) to the Lower Macleay Trailhead (here on Google Maps), completing the hike up, and then taking another rideshare from the parking lot at Pittock Mansion. 

Where to Stay in Portland, Oregon

When you’re trying to decide where to stay in Portland, the easiest way to think about the city is by splitting it between east and west along the Willamette River, which separates the west side of Portland where you’ll find downtown Portland from the east side, where you’ll find Hawthorne, Division Street, and the Alberta Arts District (among many other options). 

As a general rule, the west side is more urban, with taller buildings, more people, and fewer parks, and the east side is more residential, quiet, and low-key. That’s not to say that there aren’t some amazing things to do, see, eat, and drink on the east side – the stretches along Division, Hawthorne, Alberta, and Mississippi are packed with some of the best bars and restaurants in the city. 

The best of both worlds is the Central Eastside, which is just across the river from downtown, in a perfect central location for exploring both sides of the river. 

Here are three hotel options in Portland. 

  • Budget: If you’re on a budget and want to stay in a convenient location for exploring the city, look at the Kex Portland. It’s part boutique hotel, part upscale hostel, and has private rooms and dorms to choose from, along with a nice array of social spaces where you can mingle with other travelers. All at a surprisingly affordable rate.  
  • Mid-Range: The Ace Hotel in Downtown Portland is quintessential Portland. It’s hip (verging on hipster), there’s a Stumptown Coffee in the lobby, and the location couldn’t be better for exploring the tourist attractions downtown. 
  • Luxury: For a luxurious experience in a great location, look at The Nines, a luxury hotel in the heart of Downtown Portland. Between the great views from (some of) the rooms, the rooftop bar, and the cozy library, there are touches of luxury throughout the entire experience. 
bridge in portland

Getting Around the City

Getting around Portland is relatively smooth thanks to a robust public transit system, anchored by the MAX Light Rail lines (which get you to and from the airport in a half hour or less) and a network of buses that covers the city and surrounding suburbs. 

The Downtown core is fairly flat and walkable, though it does get hilly as you go west from downtown up into Forest Park and Washington Park.

If you don’t have a car – and you don’t necessarily need one in Portland, especially if you’re staying downtown – then rideshare companies like Lyft are a great option for getting around. You can often get from one side of the city to the other for less than $10. 

What Airport to Fly Into

The best airport to fly into in Portland – also the only airport near Portland – is Portland International Airport (PDX). PDX is a joy, filled with really good food options (for an airport) and Stumptown Coffee. It’s no wonder that it’s consistently rated at the top of any list of the best airports in the US. 

Where to Eat in Portland

Portland is a fun food city because of its diversity, both in terms of the types of cuisines you’ll find, ranging from Turkish to Venezuelan and just about everything in between, and in terms of price points. 

From the budget options you’ll often find at food carts around the city to higher end meals created by some of the best up-and-coming chefs in the country, Portland has a wealth of food options waiting for you. 

  • Pine State Biscuits: Amazing breakfast sandwiches, this is the place to go for breakfast or brunch. They have multiple locations across the city, too. 
  • Güero: Cozy spot for affordable and delicious Mexican tortas over on the east side of the river. Plus, margaritas!
  • Olympia Provisions Public House: King of sausages and charcuterie in Portland, they have a sausage garden on Division Street in Southeast Portland with a selection of their sausages, bigger Germany/Austria/Switzerland-inspired offerings like schnitzel, and of course, a wide array of local beers on tap to wash it all down. 

Authors Matt and Alysha are two west coast natives who have spent the past few years exploring every nook and cranny of the west coast of the United States, from Alysha’s home state of California up to Matt’s home state of Washington. On West Coast Wayfarers, they work with local experts to bring you the inside knowledge that only a local would know to help you fall head-over-heels in love with the west coast, just like they have.

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