City Guide

13 Must-Do Things to Do in Portland, Oregon to Make the Most Out of the City

By Landing | Jun 11, 2024
A long exposure right after sunset looking over Portland, Oregon.

Food carts, plenty of green spaces, and outdoor fairs are just a few fun things to do in Portland, Oregon. Here are 13 of Landing’s top picks.

If you’re craving a trip to an Oregon oasis, you might be ready to “keep Portland weird” like a true local. But finding the little things that make this Northwestern city a charming, authentic place isn’t always easy for first-time visitors and new residents.

You don’t have to binge-watch “Portlandia,” the Portland-based sketch comedy show that helped popularize the city, to find great spots. From doughnut runs to discovering the city’s diverse food and arts districts, here are some of the best things to do in Portland, Oregon to experience the city in all its wonderfully weird glory.

Is Portland Worth Visiting?

No matter who you are and what you like, Portland is worth a visit. But that’s especially the case if you’re a foodie. Its one-of-a-kind combination of fresh, local ingredients and diverse communities of inventive chefs is a recipe that can’t be replicated anywhere else in the U.S.

In 2024, the City of Roses was crowned the 10th best city in the world for food by Time Out Magazine and the 2nd best foodie city in America by WalletHub. Plus, the diversity of its food and BIPOC and LGBTQ+ chefs and owners was the reason Forbes chose Portland as one of the 20 best places in the U.S. to visit in 2023.

Exploring a delicious bucket list of coffee shops, food carts, and restaurants isn’t the only fun thing to do in Portland, Oregon. PDX is also home to a thriving arts community, boutique shopping, and distinct neighborhoods to explore. And one big pro of Portland is you can easily explore without a car. Its extensive TriMet transit system and bike-friendly streets make it one of the best cities to live in without a vehicle. Plus, when you need a break from city living, you can explore nature trails and open green spaces, like Forest Park and Washington Park.

Start here, live anywhere

With over 7,000 apartments in our network, you're free to roam with Landing.

Play Icon

Start here, live anywhere

13 Best Things to Do in Portland, Oregon

Whether you’re on the hunt for the best food trucks, art galleries, or neighborhoods, here are 13 top Portland experiences.

1. Become a Whiskey Connoisseur at Multnomah Whiskey Library

A view from inside Multnomah Whiskey Library, Portland, Oregon
Image source:

Portlanders love to nerd out about food and drink culture. After debating the best roast for the perfect espresso at a third-wave coffee shop, grab a nightcap at Multnomah Whiskey Library. It’s a membership-based bar that houses an extensive collection of spirits from all over the world.

Don’t worry if you aren’t a member. You can purchase a one-time “hall pass” to enjoy cocktails, taste spirits, or join a tasting night.

2. Dive Into a Literary Labyrinth at Powell’s City of Books

Corner view of Powell's CIty of Books, Portland, Oregon
Image source:

“City of Books” isn’t an understatement. Powell’s is the largest used and new bookstore in the world, housing about one million books in a shop that takes up an entire city block. It’s no wonder it’s one of the top things to do in Portland, Oregon. You can easily spend an entire day — or a whole vacation — exploring more than 3,500 book sections. And if you’re just browsing, head to the Rare Book room for an impressive collection of autographed first editions.

3. Hike the Wildwood Trail and Discover the Witch’s Castle at Forest Park

Witch's Castle at Forest Park, Oregon
Image source:

Portland is surrounded by green spaces, including America’s longest forested urban trail. The Wildwood Trail is a 30-mile hiking and biking area that runs the length of Forest Park in Northwest Portland, which is full of conifer trees and other native plants and species. It’s a relatively easy walk, making it ideal for families with kids, marathon runners, and bicyclists.

The trail also leads to the Witch’s Castle, a moss-covered stone cabin that’s the source of local ghost stories. Nearby, the French Renaissance-style Pittock Mansion is another popular museum and garden on the eastern edge of Forest Park.

4. Embark on a Culinary Adventure Through Trendy Food Carts at Prost Marketplace

Tables with diners at Prost Marketplace, Portland, Oregon
Image source:

As of 2024, there are well over 500 food carts across Portland. The city divides its carts into pods — areas where multiple carts function, often with seating and other amenities to let diners explore several at once.

There are pods all over Portland, but a good place to start is Prost! Marketplace, which is the city’s most popular pod. Surrounding one of the city’s best breweries are several carts with BBQ, tacos, and Thai food, to name a few.

5. Uncover Oregon’s Fascinating Past at the Oregon Historical Society

The entrance to the Oregon Historical Society's headquarters and museum, on Park Avenue in downtown Portland.
Image source:

Come for the eight-story-high murals and stay for the extensive collection of photographs, artifacts, and oral histories. The Oregon Historical Society is a great place for history buffs and families, with rotating exhibits that spotlight unique Portland and movements that make the city a special place to live.

6. Witness Blooming Beauty at the International Rose Test Garden

Flowers at the Rose Test Garden in Portland, Oregon.
Image source:

This city has been dubbed the City of Roses for a reason. Gazing at these stunning flowers is a must-do thing in Portland. Between late May through October, more than 10,000 individual rose bushes bloom at the International Rose Test Garden. The garden began as a testing ground for new rose varietals during WWI, when gardeners sent roses from all over the world. To learn everything your budding botanist heart desires, the garden hosts small group tours.

The International Rose Test Garden is located in Washington Park. Make a day of it and visit the Portland Japanese Garden, Oregon Zoo, and Hoyt Arboretum.

7. Support the City’s Artisans Portland Saturday Market in Waterfront Park

People waiting in line at Portland's Saturday Market.
Image source:

With the largest continuously operating open-air arts and crafts market, Portland just keeps breaking records. For 50 years, the Portland Saturday Market in Waterfront Park has spotlighted local artists and craftspeople. Tarot readers, ceramists, and jam makers are part of a diverse set of more than 150 vendors. Despite what the name suggests, the market is open every Saturday and Sunday in Washington Park.

CTA Banner

8. Hop Around Art Galleries in Alberta Arts District

A mural showing a painting of a red rose with a bicycle parked in front of it at Alberta's Art District, Portland, Oregon.
Image source:

One of Portland’s liveliest neighborhoods is the Alberta Arts District. Technically, it’s made of three neighborhoods: Vernon, King, and Concordia in Northeast Portland. This 1.5-mile stretch is full of colorful murals and art galleries that have long been an oasis to Portland’s counterculture.

For a full tour, the Last Thursday Art Walk is a cultural event where art galleries, music venues, and small businesses across all fifteen blocks host guests and special events until 9 p.m.

9. Explore Wine Country in Willamette Valley

Vineyards at Willamette Valley.
Image source:

Willamette Valley is home to two-thirds of Oregon’s wineries, which produce some of the world’s most sought-after Pinot Noirs. While the Willamette Valley stretches down to Eugene, many vineyards are just outside of Portland’s city limits. Make a weekend out of it with a stay at a B&B and enjoy a guided tour through the valley.

10. Grab Fresh Local Produce at the Portland Farmers’ Market

Portland Farmers Market near the center looking northeast in the midst of Portland State University's campus.
Image source:

With such an impressive food scene, it’s no wonder Portlanders are discerning home cooks. Portland Farmers’ Market is open every Wednesday, Saturday, and Sunday in five different neighborhoods across the city. With local produce, dairy, and handmade goods available, you can easily stock your entire kitchen exclusively with local Oregon food.

11. Do a Museum Tour Through Downtown Portland

Exterior view of the Oregon Museum of Science & Industry in Portland, Oregon.
Image source:

A unique draw to the Portland Art Museum is its spotlight on Native American and Northwest artists alongside rotating exhibits with modern and contemporary works. And while you explore Downtown Portland, you can cross the Willamette River to explore the Oregon Museum of Science and Industry.

In nearby Old Town and Pearl District, you’ll also find a handful of unique specialty museums, like the Japanese American Museum of Oregon, Portland Chinatown Museum, and the Freakybuttrue Peculiarium.

12. Catch a Show at the Pioneer Courthouse Square

Early morning view of Portland's Pioneer Courthouse Square.
Image source:

Locals know Pioneer Courthouse Square as Portland’s living room because it hosts more than 300 events a year. Even if you’re in town for a quick visit, chances are you’ll be able to catch a show. Check out its Portland activities calendar online and come hungry so you can sample one of the square’s iconic food carts.

13. Visit the World’s Smallest Park at Waterfront Park

A view of Mill Ends Park in the autumn.
Image source:

With sites like the World’s Smallest Park, it’s not hard to keep Portland weird. Mill Ends Park is a small median decorated with tiny plants on the southern side of the normal-sized Waterfront Park, which stretches across Old Town’s border with Willamette River. Once you visit, find more cool things to do in Portland, Oregon on the weekend. Shop at Portland Saturday Market, stop over for donuts at Voodoo Doughnut, and continue strolling down Waterfront Park.

Enjoy Portland Experiences With Landing

With so many fun things to do in Portland, you’ll want to stay more than a weekend. How about a month or two? Bring the weird and Landing will handle the rest with flexible, fully-furnished Portland apartments.