Only have two days in Portland, Oregon? Here are the best things to do

Photo courtesy of Joanne DiBona

Portland has beautiful skyline views

You can spend weeks, if not years, discovering the history, culture and charm of Portland, Oregon.  Even if you only have just a day or two for a visit, you can definitely get a taste – both literally and figuratively – of the city’s many attractions.

For an introductory view of the city skyline, start your adventure at the Pittock Mansion, built in 1914 and filled with the rich history of one of Portland’s first families. It's the perfect place to learn how Portland became the dynamic city it is today.

Photo courtesy of Joanne DiBona

Street art at every corner

Portland is known for its progressive urban planning, livable neighborhoods and a creative populace, so it’s no wonder that expressive street art can be found in public spaces, side streets and alleyways throughout downtown. Visitors are encouraged to put on their walking shoes (or hop on a bike share rental) and explore the murals that define this innovative metropolis.

Another excellent way to discover Portland is on an organized walking tour, which meanders through the most fascinating portions of the city and is led by expert guides who will provide you with colorful narratives of Portland's history. 

Photo courtesy of Tony DiBona

No need for a car in this transportation haven

Portland is one of the few cities in the United States where, as a resident, you can live effortlessly without a car. Visitors also benefit from the affordable, widespread transportation system available here.

For $2.50 for a 2.5 hour pass, ride the MAX Light Rail System from the Portland International Airport to downtown, then use it to get around the city. Another option is the Portland Streetcar, which also offers affordable transportation to neighborhoods around the city.

Photo courtesy of Joanne DiBona

The city's living room

Just as Times Square is the heart of New York City, Pioneer Courthouse Square serves the same role for Portland. Known as "Portland's Living Room," this public space occupies a full 40,000-square-foot city block in the heart of downtown.

The square hosts more than 300 events annually that connect the city and its residents. It's also home to a variety of food trucks that provide a diverse selection of excellent culinary offerings.

Photo courtesy of Tony DiBona

Some of the nation's best street food

Nationally known as home to some of the best street food in the U.S., enjoying a meal from a local food truck in Portland can be a true gourmet experience.

The city's food carts are unique as many are gathered in groups dubbed "pods," making it easy to sample a variety of dishes at the same time. From vegan to classic barbecue to Middle Eastern and Asian dishes, even the most discriminating tastes can find something to savor at the city’s many food truck options.

Portland: 10 Best Food Trucks in Portland, Oregon

Photo courtesy of Tony DiBona

Nature and history in Portland Japanese Garden

Acclaimed as one of the most authentic Japanese gardens in the world outside of Japan, Portland Japanese Garden is a must-see during your visit. Located in the city's Washington Park, it is a nonprofit organization encompassing 12 acres and eight separate garden styles, including an authentic Japanese tea house, meandering streams, a tea café and picturesque walkways.

In 2020, the Garden is celebrating the "Year of Peace" in recognition of  the 75th anniversary of the end of World War II, and to demonstrate how we experience peace and cultural understanding through connections to art, nature and one another. 

Photo courtesy of Tony DiBona

Portland's famous farmers market

If you're visiting on a Saturday, make sure to pay a visit to the renowned Portland Farmers Market at downtown’s Portland State University. The market boasts over 100 vendor stands, making it not only a great place to pick up fruits and veggies, but also some of the most iconic regional dishes in town.

From farm-fresh, traditional Mexican mole and deep-dish pizza to hearty breakfast sandwiches, there’s something for every taste. This is one of more than a dozen farmers markets located in areas around the city.

Photo courtesy of Joanne DiBona

Pizza and more at the Pine Street Market

The Pine Street Market in the heart of the city houses food and drink ventures by some of the city’s hottest chefs and restaurateurs. The market is open from mid-morning to late at night every day of the week, making it a perfect stop for hungry visitors.

Try the mouthwatering slices of Checkerboard Pizza (led by James Beard award-winning author and baker Ken Forkish) as well as the tasty Japanese and vegan bowls at Marukin Ramen.

Photo courtesy of Joanne DiBona

Roses everywhere

Portland has been known as the "City of Roses" for more than a century, starting in 1905 when 10,000 roses were planted along Portland's streets in commemoration of the Lewis and Clark Centennial Exposition world's fair.

If you're visiting between April through October, with the peak in June, make it a point to visit the International Rose Test Garden (next to the Japanese Garden) and delight in more than 10,000 rose bushes of approximately 610 varieties.

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Portland is also known as 'Beervana'

Portland houses more than 75 breweries with that number only ticking up, making it one of the major beer capitals in the world. Since the early 1980s, the craft beer movement has been going strong. The bustling brewpubs and countless beer-themed events support its "Beervana" nickname. Prost!

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The consummate bookstore for bookworms

Book lovers of all ages will delight in a visit to Powell’s City of Books, which occupies an entire city block in downtown Portland. It claims to be the largest independent new and used bookstore in the world, boasting 1.6 acres of retail floor space, with a mind-boggling inventory of volumes from around the world.

Photo courtesy of Joanne DiBona

Wine time

While beer is king in Portland, wine is definitely a close second. The Willamette Valley in Portland's backyard is home to picturesque wineries well worth a tour and tasting.

For an exceptional experience, venture out to the eclectic North Mississippi neighborhood and enjoy a wine tasting at the Southeast Wine Collective. Excellent wines paired with outstanding, homemade hors d'oeuvres take this tasting to the next level.

Photo courtesy of Joanne DiBona

Portland's Chinatown

While strolling through Portland’s Old Town, you can’t miss the colorful entrance to Chinatown, where you’ll find many Chinese restaurants, gift and import shops, herbal medicine stores and Asian food markets. You may notice that the street signs are both in English and traditional Chinese characters.

Photo courtesy of Joanne DiBona

Strolling down the river

Discover the beauty of the Willamette River and Portland's neighborhoods on a stroll down Tom McCall Waterfront Park, a favorite among cyclists, runners and walkers.

Once the site of a freeway (and named after Oregon Governor Tom McCall, a staunch advocate of recycling, environmental preservation and urban planning), this 1.5-mile stretch of green is home to many annual events, such as the Portland Rose and Waterfront Blues festivals.

Photo courtesy of Joanne DiBona

Architectural details abound

As you meander through Portland's city sections and neighborhoods, you'll marvel at a variety of architectural styles that span several centuries. The 19th century buildings are especially stunning, with their dramatic exteriors featuring intricate details.

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Photo courtesy of Tony DiBona

Share a plate with family and friends

Enjoy succulent steak slices at Tasty n Alder in downtown Portland, which features a family-style menu of innovative dishes with diverse international origins. Select from a wide variety of menu items in a relaxed, festive open-space environment that encourages shared plates. It's a fun and delectable dining experience.

Photo courtesy of Joanne DiBona

Explore the artsy Mississippi neighborhood

With easy access to MAX Light Rail and a rapidly emerging retail and dining scene, North Mississippi Avenue has become one of the city's hottest thoroughfares for strolling, shopping and dining. Here's where you'll find some vintage buildings and newer, eco-friendly, mixed use construction in addition to eclectic eateries, nightspots and highly popular food-cart pods.

Photo courtesy of Joanne DiBona

While away happy hours

Portland is a fantastic place to enjoy an afternoon happy hour, but it also comes alive after dark, with restaurants, clubs, theaters and entertainment venues open late all over town.

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Photo courtesy of Tony DiBona

Vintage salute to Portland

One of the last quirky sights you may see when leaving Portland is the "Portland, Oregon" neon sign (a.k.a. the White Stag sign). Built in 1940 to advertise White Satin sugar, the sign is now a City of Portland Historic Landmark and is considered one of the most identifiable parts of the city’s skyline.