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Funky, historic Portland has constant surprises for savvy travellers

I like neon signs, heritage houses, mid-century furniture and retro clothes, so Portland, with its distinctive vintage communities, is one of my favourite destinations to explore.

Portland, Oregon, exudes vintage vibes.

Whenever I approach Portland’s downtown and look up at its iconic “Portland Oregon” neon sign, with a state outline, white stag and the words “old town,” I know this is my kind of place.

I have an affinity for the “good old days.” I like neon signs, heritage houses, mid-century furniture and retro clothes, so Portland, with its distinctive vintage communities, is one of my favourite destinations to explore.

Over three days here, I’ll watch an old sport made new by the city’s beloved “Rose City Rollers,” a female and gender-expansive roller derby league, tour the 1912 Pittock Mansion, enjoy an old-fashioned high tea in the historic Woodlark Hotel and visit some vintage stops, common throughout Portland and its neighbouring suburbs.

My first night on the town takes me to the Hangar at Oaks Amusement Park to see roller derby, which began in the 1930s, fell out of favour, then had several resurgences over the ensuing decades. The most recent was 20 years ago when Rose City Rollers co-founder and executive director Kim Stegeman got together with friends at a local bar, and decided Portland needed to bring roller derby back. The year was 2004, a year after Portland had embraced the slogan “Keep Portland Weird.”

“I grew up working in a roller rink so I was naturally good at skating. I was with another friend who played in bands and was a good skater and Jeffrey Wonderful, who was into Portland Organic Wrestling and put on rock operas. We were all a part of wanting Portland to be fun and cool,” she says.

The friends put an ad in the Portland Mercury to try and recruit fellow roller skaters, and to their surprise 80 people showed up wanting to join.

Stegeman, 28 at the time, became the captain of Guns N’ Rollers, named after the rock band Guns N’ Roses, and whenever she laced up her roller skates she became Rocket Mean, from the band’s song Rocket Queen. Her teammates also had names inspired by Guns N’ Roses’ songs, like November Pain (November Rain), Paradise Kitty (Paradise City) and Bitter Sweet Child O’ Mine” (Sweet Child O’ Mine).

“We were a lot more campy back then. Our uniforms fell apart because we had home-made stuff, but now we use derby company uniforms,” she says, noting fishnet stockings and a tennis skirt over “short shorts” used to be her norm.

While the uniform quality has improved, many league players today still go by theatrical names like Amera-Can Gangster, Doctor of Destruction, and Freddy HerFury as they confidently roll around a flat, oval track showing off their athleticism and strategy.

The Saturday night I checked out the Rose City Rollers, a doubleheader was happening that included a match between Guns N’ Rollers and the Heartless Heathers. The bout attracted a lively crowd of 430 people, most sitting on five-row-high bleachers, who clapped and cheered as an announcer called out the action and upbeat music blared.

The Rose City Rollers league has grown to 500 players, between the ages of seven and 65, who play on 18 teams, making it the biggest roller derby league in the world, according to Stegeman.

“Roller derby is becoming as popular as it was when it was started in the 1930s, by Leo Seltzer,” she says, of the sports’ founder. Seltzer, a Chicago event promoter, was the first to bring a show on wheels to the public, after reading more than 90 per cent of Americans had roller-skated at one point in their lives.

While the Rose City Rollers continues to flourish, attracting new fans to this vintage sport, the most significant indicator of Portland’s vintage vibe has to be its numerous vintage shops. Antique malls, vintage clothing stores and second-hand thrift shops make Portland one of the best destinations for vintage aficionados.

Portland resident Cathy Steward has been scouring the city’s vintage shops for 50 years, and was busy checking out bins in the back of Monticello Antique Marketplace when we met.

“For me, I see things that remind me of times when I was a kid and sometimes I’ll find something that’s so unusual I know I’m not going to find it again so I’d better get it now,” she says.

Her vintage obsession started with a porcelain doll from the 1800s.

“My great-grandmother promised me one when I was little. I didn’t know where it went, when she died, so I was on this quest to find one like it. Now when I see them I get them,” she says, adding she’s found eight so far.

Stars Antiques vendor David Barrs has been selling in the mall for the past six of its 34-year history, specializing in mid-century, vintage toys, records and clothes.

“To me there’s a big DIY element to Portland and a lot of variety here. It’s part of the hipster culture of Portland,” he says. “When you walk the city streets and the suburbs you’ll see people with a lot of different styles and interests. It’s an alternative culture, lifestyle and the past offers an opportunity to pick up unique, eccentric things.”

As a longtime vintage collector, I have to agree — although I’m more cautious these days and not actively pursuing additions to my Japanese head vases or 1960s Howard Holt collection. But when I came across a porcelain dog figurine in Portland, reminding me of my two cocker spaniels at home, it proved too hard to resist, especially at the bargain price of $6 US, with the bonus of no taxes. (Another reason to love Portland — it’s one of the few U.S. cities with no sales tax).

Where to stay in Portland

The Nines, in a prime downtown location directly across from Pioneer Square, is housed in the Meier & Frank building, built in 1909.

Meier & Frank was a pre-eminent department store where Clark Gable once worked before he became an actor. In 2005, the top nine floors were transformed into a luxury hotel, named in honour of its early department-store history when people came to be “dressed to the nines.”  The spacious rooms have a touch of glamour, with damask drapes, glittering lighting and great city views.

The best view is from the hotel’s rooftop deck in Departure restaurant on the 15th floor, serving modern Asian cuisine. The hotel’s other restaurant is Urban Farmer, which has a country-chic ambience and is a good choice for breakfast before heading out to explore the city. (It also serves lunch and dinner, and is known as one of the top steakhouses in downtown Portland.)

Where to eat in Portland

Lilia Comedor Restaurant, which made the New York Times 2023 list of best U.S. restaurants, was a standout, serving Pacific Northwest cuisine by Mexican-American executive chef Juan Gomez. My favourite dish was a spicy swordfish a la brasa, with a mole manchamanteles on coconut rice with poached kumquat. I would have re-ordered this dish any time I visit Portland in the future, but with the menu changing on a weekly basis it might not be possible. Gone (for now) but definitely not forgotten. Gomez’s commitment to fresh means he sources from Oregon and Washington food producers, but he has gone as far as Vancouver for a wild berry called sea buckthorn, which he’s incorporated into a mole chili dish. His pastry-chef wife, Samantha Cameron, was equally creative with her desserts, from a fancy Limecicle Baked Alaska to a humble, but delicious, apple cider beignet.

My only regret dining at Amaterra Restaurant, in a winery just minutes from downtown, was not arriving before dark to enjoy its sweeping views of the Willamette Valley. The modern restaurant features mouthwatering seafood dishes, such as dungeness crab cakes, oven-roasted salmon in minestrone, and a pan-roasted Columbia River Sturgeon, which were all very flavourful and fresh. While I tried not to fill up before the mains arrived, the restaurant’s house-made fagoza bread, with cheese and herbs, was impossible to resist and well worth the calories.

Abigail Hall, a 40-seat cocktail bar in the historic Woodlark Hotel in downtown Portland, swaps out its martini glasses for vintage tea cups on weekends, for those of us who enjoy an old-fashioned high tea (servings are 11 a.m., 1 p.m. and 3 p.m.). This cosy space, which features a fireplace and wainscot walls from 1907, is located in the hotel’s original ladies reception hall in the former Cornelius Hotel — the perfect setting to eat a tower of treats, such as fresh-baked scones and finger sandwiches. The floral walls are hand-painted by a local artist.

Kim Pemberton was hosted by Travel Portland, which did not review or approve this story. Follow her on Instagram at kimstravelogue.