Portland, Oregon: Unique and Weird Stuff to Do

By Katherine Rodeghier

Portland, Oregon, gained a reputation for being weird and loving it: naked bike rides, a vegan strip club, the setting for the offbeat “Portlandia” comedy TV show, and a penchant for free expression, hipster fashions, and beards.

But if you don’t embrace the bohemian lifestyle, is Portland for you?

Yes! My husband and I, staid suburbanites of a certain age, found plenty to do without fear of fitting in.

Homelessness Still a Problem

But I did worry about news reports of Portland’s homelessness problem and associated crime. My fear proved unfounded.

We saw makeshift shelters and tents along the major streets going to and from the airport, but none where we stayed downtown or in any of the places we visited.

We weren’t harassed by panhandlers. On a walk outside the downtown area, we saw a young man seemingly strung out on drugs, but he posed no danger to us, just himself, sadly.

Portland is taking a humane and caring approach to helping those experiencing homelessness by striving to provide stable housing and mental health treatment.

It’s also making progress in ending unsanctioned camping by opening Safe Rest Villages with access to shelter and services, as well as fast-tracking construction of affordable housing.

Stop and Smell the Roses

Rose bushes for sale in my local garden center might have had their roots in Portland. Some commercial growers try out new varieties at the International Rose Test Garden because the city’s climate is conducive to propagating the fragrant flower.

The garden began during World War I when hybrid roses from around the globe were moved to Portland for safekeeping. Now the oldest continuously operated public rose test garden in the nation has more than 10,000 rose bushes and more than 610 varieties.

Perched on a hill in Washington Park, the terraced gardens have a view of downtown and, on a clear day, Mount Hood.

A note about those clear days: Odds are better in summer. Most of the city’s 36 inches of precipitation per year fall from late autumn to early spring.

The best time to see roses in bloom is late May to October, but the garden remains open year-round free of charge.

I especially enjoyed the Shakespearean Garden with plants mentioned in the works of the Bard. “A rose by any other name would smell as sweet,” says Juliet to her Romeo.

Mansion on a Hill

Portland became obsessed with roses long before the first spade of dirt was turned in the test garden thanks to socialite Georgiana Burton Pittock.

She founded the Portland Rose Society in 1889 and anyone who was anyone planted the bushes. Roses even bordered the streets of what became known as “The City of Roses.”

We had a glimpse into Portland’s gilded age on a visit to the Pittock Mansion,  home of Georgiana and her husband, Henry Pittock.

He traveled to Portland on the Oregon Trail at age 19 to seek his fortune, eventually became publisher of The Oregonian newspaper, and grew rich through investments in real estate, banking, railroads, steamboats, sheep ranching, silver mining, and the paper industry.

The Pittocks built their French Renaissance chateau on a hill nearly 1,000 feet above the city with a terraced garden where, on one of those prized clear days, we spotted a snowcapped Mount Hood poking through low-lying clouds.

Family members lived in the mansion until the 1950s. After a 1962 storm left it severely damaged it fell into ruin.

Developers planned to tear it down to build a subdivision, but residents rallied to restore the home and preserve the grounds.

They are now a city park and museum. Donated art and antique furnishings fill 23 rooms along with exhibits devoted to Portland history.

Heaven for Book Lovers

Portland has plenty of stores selling far-out fashions, but not to my plebian taste. Instead, we spent our shopping hours nerding-out at Powell’s City of Books.

City is an apt name for the store because its four floors fill an entire city block in downtown Portland’s Pearl District.

The world’s largest new and used independent bookstore, it has more than a million volumes divided into nine color-coded rooms with more than 3,500 different sections.

Its Rare Book Room draws bibliophiles to Portland to search for hard-to-find books and autographed first editions. Writers, artists, and thinkers visit to read in the Basil Hallward Gallery.

I roamed room after room, examined a display of banned books, checked out the pastries in the café, and perused racks of gift items. Rows of novelty socks were emblazoned with slogans sassy and profane. Weird, maybe, but wonderfully funny.

Book lovers who worry their purchases won’t fit in their suitcase need not hold back their buying frenzy. Purchase at least $50 worth of books and Powell’s will ship them home, at no charge.

Dining on the Go in Portland

Portland was an early adopter of food carts, but the craze spread to so many cities that food trucks and carts no longer seem weird. The sheer number in Portland remains unusual, though.

It has more than 1,000, according to Michelle Bergey, co-founder of Lost Plate Food Tours. We sampled foods from seven carts on her Portland Food Carts, Pods & Patios Tour.

Unlike roving food trucks, carts remain in one spot, often grouped together in pods. Rather than mediocre street grub, they serve foods made from scratch using regional ingredients.

Cheese curds from a local dairy flavored hearty poutine from the Potato Champion cart in a pod on Portland’s central east side.

At nearby Hawthorne Asylum Food Carts, on the grounds of a former mental hospital, foods have an ethnic flair. We sampled Burmese noodle salad, a Dutch waffle stuffed with jam and Bavarian cream, fried cauliflower akin to Iraqi street food, and chicken dumplings made from a Ukrainian family recipe.

We moved to Morrison Market Food Hall for tacos wrapped in warm tortillas made by the owner’s mom.

The tour ended on a spacious patio at Rogue Brewery where flights of craft beers accompanied platters of pub pretzels just like those we’d enjoyed in Germany.

A Peaceful Garden

In the 1950s, U.S. cities began creating Japanese gardens as a symbol of peace between former World War II enemies.

Portland got its chance when it closed its zoo in Washington Park and transformed the site into the most authentic Japanese garden outside Japan.

Opened in 1963 and now covering 12 acres, Portland Japanese Garden encompasses eight garden styles entwined with streams and walkways.

We didn’t let the rain stop us from exploring this serene setting, especially its newest addition, the Cultural Village opened in 2017.

Architect Kengo Kuma and third-generation Japanese gardener Sadafumi Uchiyama designed the $33.5 million expansion as a place to immerse in traditional Japanese arts and culture.

Emulating Japan’s “temple towns” surrounding sacred shrines, it has an authentic medieval castle wall 185 feet long and 18.5 feet high built with traditional hand tools under the direction of a Japanese master stone mason.

After strolling past lacy Japanese maples, trickling waterfalls, and an authentic Japanese tea house (demonstrations only) we shook out our umbrellas and relaxed over tea and Japanese snacks at the garden’s Umami Café.

Resembling Kyoto’s Kiyomizu-dera temple, the glass-enclosed building appears to float over a hillside and offers expansive views of the surrounding forest.

Emphasis on Indigenous Art

Opened in 1892, the Portland Art Museum ranks as the oldest museum on the West Coast and the largest in Oregon with more than 42,000 objects displayed in two connected buildings.

Sadly, our time in Portland was running out so we missed much of its collection. Breezing by Renoirs, Van Goghs, and Monets, we made a beeline to the museum’s second- and third-floor galleries holding the collection for which it may be best known: Native American art.

Remarkable for its depth and diversity, it contains 3,500 prehistoric and historic objects from 200 cultural groups throughout North America.

We gazed at works by Native American masters as well as those by regional contemporary artists.

An elaborately carved and painted dugout canoe drew oohs and aahs from school children on tour. I was mesmerized by a tall figure in full dance regalia made by Calvin Hunt Jr. mingling wood, paint, feathers, string, canvas, and cloth.

I loved that galleries are divided into cultural regions: the Northwest Coast, the Arctic, Plains, Woodlands, California, and the Southwest.

Two galleries are devoted to Native American art from the nearby regions of western Oregon and the Columbia Plateau. Another displays Pre-Columbian art from Central and South America.

Napa of the North

We left Portland behind us for a few hours to tour the Willamette Valley where two-thirds of Oregon’s wines are produced.

Emigrants heading west on the Oregon Trail in the 1800s were drawn to the 150-mile-long valley reputed to be “the land of milk and honey.”

In the 1970s and ’80s, winemakers, including many from California, moved in and began producing award-winning wines.

Around Portland Tours customized a day trip for us with stops at two of the valley’s more than 700 wineries.

Dana Blizzard, owner and winemaker at Blizzard Wines & Vineyard, greeted us in the winery’s tasting room. As we sipped from four pours, she told us her parents bought their house for its view of the vineyard then planted with so-called “suitcase varietals,” clones of vines from France.

She grew up on the land and started making wine in her parent’s garage. Her husband, Nick, designed the winery building they opened in 2017 with just three wines to sell. Now they offer 16 plus artisan Champagnes they import from France.

At Dominio IV Wines,  we took the advice of tasting room manager Katie Wise and explored the grounds, glasses in hand. We relaxed with a couple of our five samples on the porch of a 1916 farmhouse before refilling and heading to a 100-year-old red barn used as a weddings and special events venue.

From the hayloft, we had a fine view of the vineyards where settlers from the Oregon Trail once grew apples, cherries, and other crops.

A Gorgeous Waterfall Multnomah Falls

Around Portland Tours also offers regular tours to Multnomah Falls 30 miles east of downtown Portland in the Columbia River Gorge National Scenic Area.

Oregon’s tallest waterfall at 620 feet ranks as the most visited natural recreation site in the Pacific Northwest drawing more than two million visitors annually. Timed-use permits are necessary to access the falls during peak season, spring into fall.

Two-Drop Cascade

The two-drop cascade can be enjoyed from a bridge crossing the flow partway up the mountain, viewing platforms and a hiking trail leading to the top. Multnomah Falls Lodge has a visitor center, restaurant, and restrooms.

Multnomah is one of as many as 77 waterfalls on the Oregon side of the 85-mile-long Columbia River Gorge National Scenic Area earning it the moniker “Waterfall Alley.”

Some, like Multnomah, gush year-round, while others just trickle during peak water flow.

Getting to the waterfalls on the Historic Columbia River Highway is part of the adventure with stops at Vista House, a 1918 rest stop on the National Register of Historic Places, and Crown Point for a view from the top of the gorge to the river 693 feet below.

Katherine Rodeghier is an award-winning travel journalist. She began as the travel editor at the Chicago Daily Herald and continues as a freelance contributor to outlets including the Chicago Tribune, Los Angeles Times, several AAA regional magazines,  and Cruise Critic. She lives in Western Springs IL.

This article was based on a media trip sponsored by Travel Portland, but the author’s opinions are her own.