Fun Things to Do in Downtown Portland

This article was updated on September 11, 2026.

Fun Things to Do in Downtown Portland, Oregon

On my first visit to the Pacific Northwest, I spent four days in Portland, Oregon. I wandered around downtown Portland, ate plates of delicious food––Portland is arguable one of the top food cities in the US. You’ll struggle to find a bad meal there. I also drank my share of local wines, hit a coffee shop, and explored some of the city’s beautiful parks. I experienced a lot of Portland in those four days.

What is Portland like?

Portland is a laid-back town. I figured as much, but I had no idea how friendly of a place it is. I met people everywhere I went. A lot of transplants from all over the country have flocked to PDX. The city has become a favorite destination to visit, but it’s also a terrific place to live.

Hotels near downtown Portland

I stayed at The Porter in Downtown Portland and I loved the location and enjoyed my time there. The Kimpton Hotel Vintage is also a favorite. And Portland now has a Ritz-Carlton if you prefer an ultra-luxury hotel.

{Book your hotel in Downtown Portland early.}

Have you made the trip to Portland? Here are some highlights and fun things to do in downtown Portland.

Hang out at Tom McCall Waterfront Park

98 SW Naito Pkwy

Since I stayed at a lovely Hilton Curio Collection hotel called The Porter, (I highly recommend), I found myself about two minutes from the Willamette River and Tom McCall Waterfront Park. It’s a place where Portlanders jog, bike, stroll, and meet up, and also provides panoramic views of the city’s bridges. The park entrance closest to The Porter was also close to the Hawthorne Bridge, one of 12 bridges in Portland. Overall, this park is a peaceful respite from the city – I visited more than once during my stay in downtown Portland.

{Here’s a very affordable walking out to hit Portland’s highlights}

Shop at Portland Saturday Market

2 SW Naito Pkwy

In this guide to downtown Portland, I couldn’t skip the Portland Saturday Market. To get a feel for local life and the people of any city, I make it a point to visit the markets. The largest continuously operating outdoor market in the country, this arts, crafts and food emporium is open every Saturday and Sunday from March through Christmas Eve. The energy here is palpable! The market is packed with Portlanders so it epitomizes the true spirit of the city. Spending some time (and money) here is also a great way to support the local artists and business owners.

{I recommend a day trip to the Willamette Valley, one of the world’s premier regions for Pinot Noir only about an hour from Portland}

{This Longchamp tote is the best for exploring Portland, or any city.}

Eat mussels at Higgins Restaurant & Bar

1239 SW Broadway

I’ve tasted my share of mussels, but the bowl I ate at Higgins – a landmark in downtown Portland’s dining scene – had to be some of plumpest and most succulent  I’ve had anywhere. Why are they so yummy? While many mussels hails fro PEI (Prince Edward Island), these are  Totten Inlet mussels from the Puget Sound in Washington State and they were so darn good. They were cooked perfectly and had some spice! The gazpacho was like none I’ve eaten before either. The chilled soup was garnished with Oregon Bay shrimp and cucumber. I sat in the bar, which felt like an old Parisian bistro. It was fabulous.

People watch at Pioneer Courthouse Square

701 SW 6th Ave

Portland’s living room attracts all kinds, making the urban park a fantastic spot to people watch. Since it’s in the heart of downtown, Pioneer Square is a good place to meet or begin and end a city tour (some walking tours start here). Live music and other events take place year round so there’s always something fun going on. Grab a bite to eat from one of the nearby food trucks and each lunch on the steps.

Are you from outside the United States and interested in touring Portland on your own? Purchase an eSIM from Truely, so you can easily navigate the city.

Suck down oysters and beer at Dan & Louis Oyster Bar

208 SW Ankeny St

When I think of old school, I imagine a place like Dan & Louis Oyster Bar. This five-generation family eatery has been shucking oysters since 1907. I opted for a half dozen with a pint of  Pfriem Pilsner (Oregon) and the combo really hit the spot. Dan & Louis serves more than oysters – fish tacos, clams beurre blanc and buttermilk fried chicken round out the food choices and the bar pours a good selection of local wine. Beyond my bivalves and brew, I loved the grittiness of this oyster bar. The service was friendly, too.

{To hit the edible highlights, try one of Portland’s best food tours}

Browse Powell’s Books

1005 W Burnside St

As a New Yorker, I adore the Strand Bookstore, so I had to make a stop at Powell’s and see if a West Coast bookshop could compete with an icon on the East Coast. With 68,000 square feet, nine rooms, three floors sand 3,500 sections, it claims to be the largest independent bookstore in the world. And I must say, Powell’s lived up to the hype. The flagship has been around since 1971 and stocks more than one million titles, aiming to connect readers with books they’ll love. It’s also open 365 days a year and has its own coffee shop. Don’t be freaked out if you get lost in Powell’s. It’s a good thing.

Experience Lan Su Chinese Garden

239 NW Everett St

Every guide to downtown Portland should include the Lan Su Chinese Garden. An idyllic retreat away from that big city vibe, this garden occupies one city block in Chinatown/Old Town. Most of the 400 species of plants in Lan Su are indigenous to China but were grown in Oregon, some more than 100 years old. Modeled after the Classical Gardens in Suzhou, the plot features a Chinese tea house, covered walkways, bridges and pavilions and Lake Zither, an artificial body of water in the center. Su is derived from Suzhou, and Lan, from Portland – after all, Suzhou and Portland have been sister cities since 1988.

Things to know about Portland

Portlanders often refer to the city as PDX, which is also the airport code. You’ll see and hear PDX a lot.

Getting around Portland

Portland has a comprehensive public transit system. There are street cars, TriMet buses and light rail. I was focusing mostly on downtown this trip so I put on my New Yorker shoes and walked just about everywhere, so I didn’t need public transportation. I took two Ubers and they were pretty reasonable. Lyft is also popular in Portland. And there’s a bike share program too.

Safety in Portland

Parts of Portland are pretty sleepy at night (I am used to Manhattan where there’s always something going on), but for the most part, the city is safe. (Just remember that it is a big city.) Some people comment that Portland has a “sketchy” feel. There is still a bit of grit left to the city (Keep Portland weird!) but I wandered around myself and never felt unsafe. Sadly, like New York, there is a substantial homeless population, but unlike New York, these people do not harass tourists, so no worries there.

Portland’s culinary offerings

The food scene is serious. If you’re heard that Portland has some great restaurants, that is an understatement. There is so much food to be had in Portland, even street food. I didn’t have enough time to eat all that I wanted. I’d go back just to eat.

And drink the wine. So much of the wine comes from the Willamette Valley, which is only about an hour’s drive from downtown. It’s one of the most recognized wine regions in the world, especially for Pinot Noir. I left PDX for two nights and hung out in McMinnville (in the Willamette Valley) and tasted a lot of Pinot Noir, so I can vouch because I was there. Oregon wines are outstanding, so if you’re a wine lover, you must go to the state just for the wine. There’s also incredible wine in southern Oregon. It’s several hours from Portland and a lovely drive.

And then there’s beer, lots of local brews for beer drinkers. And of course, coffee everywhere. The town must run on caffeine. Even I had to have a cup of local Joe while I was in Portland (I’m not a big coffee drinker).

Beautiful parks in downtown Portland

Of all the things to do in downtown Portland – and there are too many to count – the green spaces can’t be missed.  Little pocket parks throughout downtown provide spots to relax and take in nature. And public art is abundant. Permanent art installations are part of the cityscape of Portland.

The Costs

Portland is not an inexpensive city. I was thinking that costs in Portland would be a lot lower than NYC, but they weren’t. Portland hotels will likely cost less, but expect to pay about the same for food and drink (maybe 10 or 20% less). Some locals told me that rents continue to increase because of the popularity of Portland. Many people have relocated to the area in recent years and that alone is driving up prices.

The People

Portlanders are fabulous. While I loved exploring the city, I was able to connect with many people on this trip. It’s an easy city to make friends, and all the fun things to do in Portland aside, the people are reason enough to visit a second time.

Portland, until we meet again….

Many thanks to The Porter and Travel Portland for hosting me on this trip. 

Also, things to do in Milan, Italy.  And Liege, a beautiful city in Belgium. Plus, Switzerland.

Music City is another fantastic town! And explore the Umpqua Valley wine region while you’re in Oregon.