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Manitoba’s capital is an artsy, chill place that is tired of your condescending ‘Winter-peg’ jokes. Canadians should get to know it better. So I set out to do that

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Look past the chilly bleakness of Winnipeg's Main Street and you may notice the city's atmosphere of what poet laureate Chimwemwe Undi calls 'relentless hope.'Shannon VanRaes/The Globe and Mail

If you don’t live in or come from Winnipeg, what you know about the place is probably some version of the following:

It is home to broad swathes of grinding poverty. Crime, especially of the violent sort, is distressingly common. The city has a large urban Indigenous population that bears the brunt of those issues. Less weighty, but still painted in bleak shades, is the fact that Winnipeg’s winters are brutal and summer mosquito season will make you pray for winter.

So: A scrubby little town marooned in the middle of nowhere, with deep, frightening problems, a cruel joke of a climate and a hockey team they loved and then lost for 15 years.

Now, here is the Winnipeg I met when I visited for the first time to report this story. Its downtown buildings are grandly beautiful like a miniature Chicago, partly because both cities were railway hubs rolling in money 150 years ago. It has blocks and businesses so pretty that they film Hallmark Christmas movies there. And while Winnipeg is no small town – it has a population of 750,000 – it still punches above its weight in art and music and culture and restaurants.

The thing about the cold is true – that wind at Portage and Main will flay the skin right off your bones – but almost anyone you ask draws a straight line from the harsh climate to the city’s creative, collective spirit: A hobby gets you through winter, and there’s a sense of solidarity with everyone else toughing it out like you are.

If Canada were a high school, Winnipeg would be the overlooked, artsy, chill kid who would have been the most fun person by far to be friends with – if only you were smart enough to figure that out before graduation.

And now, there is a new provincial government led by NDP Premier Wab Kinew – the first First Nations Premier of a Canadian province – at work beneath the gleaming feet of the Golden Boy, the famous sculptural symbol of youth and enterprise perched atop the Legislature building. There is a new-ish Mayor, Scott Gillingham, elected a year ago with a pitch to unify Winnipeggers.

Within the city, there is a sense of movement, energy and what Winnipeg’s poet laureate, Chimwemwe Undi, calls its “relentless hope.”

In an attempt to get a truer picture of the place that often gets painted as Canada’s problem child, I contacted more than a dozen people deeply embedded in different facets of Winnipeg life and asked them what everyone gets wrong about their city, and what they want people to know about it. Then I asked them to take me to their favourite place in town, the spot that is their quintessential Winnipeg.

What I found is not some grey-brown smudge on the edge of the Prairies, but a beautiful, winsome, urban, creative, smartass, fun, livable – and, yes, profoundly challenged – city that does not deserve anyone’s condescension.

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The Canadian Museum for Human Rights lies near the Forks, the junction of the Red and Assiniboine rivers where First Nations met for thousands of years before the city of Winnipeg was built.Shannon VanRaes/The Globe and Mail

When I asked landscape architect Monica Giesbrecht what she loves about Winnipeg, she went straight to how she got here.

Her family was living in communist Romania when her father defected in 1981, and upon arrival in Montreal, officials conducted an entry interview to assess his skills. He just happened to be a professional ballet dancer, and the Royal Winnipeg Ballet just happened to be looking for a Russian-trained classical dancer to teach classes. So off he went to the city where he was apparently meant to be.

It took three years to raise the funds and extract his family from Romania. “By the time we moved here, my dad – through the ballet and through just Winnipeg being Winnipeg, which is the point of your question – had just met a bunch of people who kinda adopted him,” Ms. Giesbrecht said. “So we were met at the airport – I’m gonna cry – by 20 people.”

And she did start weeping as she laid out the rest of the story. She’d arrived as a freaked-out nine-year-old who’d left behind everything she knew. And here was this welcoming crowd with her dad who brought parkas for her and her sister, and helped her family find a bigger apartment, and a good school, and then just kept looking after them any way they could.

She grinned through tears as she summed it all up: “And anyway: Winnipeg!”

Yep: Winnipeg. When I was planning my visit, three different interview sources insisted they would drive me to or from the airport. So it seems that even vastly less worthy subjects than families fleeing a totalitarian regime benefit from the city’s down-to-earth generosity.

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The Winnipeg Art Gallery is home to the Visible Vault, shown in 2022, a display case for thousands of artworks.Jessica Lee/The Globe and Mail

Ms. Giesbrecht told her story over lattes in the café at the Winnipeg Art Gallery, one of her favourite haunts. At her back, the astonishing Visible Vault – a monumental, curvaceous glass pillar that displays a collection of contemporary Inuit carvings like jewels in a boutique – glittered in the endless Manitoba sunshine.

A principal at HTFC Planning & Design, Ms. Giesbrecht now gets to help shape the city that enveloped her family four decades ago. She worked on the urban site and rooftop development for the Winnipeg Art Gallery’s Qaumajuq Inuit art centre, and on Millennium Library Park downtown, but some of the projects closest to her heart were undertaken with community groups. That includes Selkirk Plaza, where a mural, basketball hoops and walls that double as benches transformed a parking lot into a hangout for at-risk youth in the North End.

Ms. Giesbrecht also worked on The Leaf, the jaw-dropping eight-storey, $130-million greenhouse that swoops out of the middle of Assiniboine Park. Inside is a tropical jungle of Jurassic Park proportions, a terraced Mediterranean dreamscape, a butterfly garden and the largest indoor waterfall in Canada. Wandering among the 12,000 plants is giddy, childlike magic; I never knew how a pineapple grew until I visited Winnipeg in November.

Ms. Giesbrecht travels frequently, and when people hear where she’s from, the grim stereotypes come out. “I often get it in the context of someone trying to be very nice, who will say things like, ‘You’re so good at what you do, I can’t believe you ended up staying in Winnipeg,’” she said. “And I’m just like, ‘Well, thanks. Thanks a lot.’”

There’s a dumb irony to this. The unlivable nature of Canadian cities of any size is a crisis right now, and Winnipeg gets sneering condescension while Ms. Giesbrecht and her fellow Winnipeggers adore it for providing a life impossible in so many other places: Reasonable housing costs. Easy commutes. Cottage country and natural playgrounds a short drive away.

But just like the harsh winters have fostered some of Winnipeg’s most admirable qualities, being constantly underestimated has, too. “When you kind of are used to the world thinking of you a certain way, but you know you’re not, you have to have a sense of humour about it,” Ms. Giesbrecht said. “I don’t know how you would not.”

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Portage and Main, as it looked in the 1890s and today. A bunker-like entryway leads to a pedestrian tunnel.Cartwright and Lucas, Winnipeg, 1923; Shannon VanRaes/The Globe and Mail

“Occasionally employed historians” Sabrina Janke and Alex Judge created a podcast about Winnipeg’s past called One Great History (riffing on the “One Great City” signs that used to greet visitors driving into town). They started with a glossary of extremely Winnipeg things, explaining socials (a pre-wedding fundraiser featuring prizes, food and drinking), dainties (a platter of assorted little pastries) and the phenomenon by which you will find a dude in cargo shorts waiting at a bus stop somewhere in the city, no matter how cold it is.

The emotional tone of the podcast – self-deprecating mockery mixed with deep, genuine affection – is something you hear a lot when Winnipeg talks about itself. The chorus of The Weakerthans song One Great City is a clanging “I hate Winnipeg,” but a closer read of the lyrics reveals a furiously loving portrait rendered in finely observed detail.

Frankly, Toronto or Montreal or Vancouver would never be cool enough to laugh at themselves the way The ‘Peg does.

“We do highbrow and lowbrow in this excellent way in Winnipeg,” city Councillor Sherri Rollins told me over the phone, as we arranged to meet at one of about a dozen places she wanted to show me. Highbrow: the Royal Winnipeg Ballet, the Royal Manitoba Theatre Centre, the Winnipeg Symphony Orchestra, the Canadian Museum of Human Rights. And lowbrow: “We like our Giant Tiger. We like our like ice cream shops. We like hanging out at Dollarama,” she said.

In the end, she took me to Baked Expectations, an open-late coffee shop that’s been a city icon for 40 years. Its curved front windows, black-and-white checkered floor and neon signs are pure retro charm, and its dessert case was stuffed with impossibly elaborate cakes that looked like scratch ‘n sniff stickers come to life.

Ms. Rollins had never been to Winnipeg when she moved from Ottawa as a student, and then fell in love with the place. She kept returning to a series of dualities to explain it: The fancy and the humble; the self-mockery and pride; the kind of storybook urban beauty that leads to the most anodyne, cozy entertainment on Earth – Hallmark movies – being filmed in what is, really, an edgy city.

“And oftentimes I think Winnipeggers don’t look out into what’s going on in other cities, so they don’t actually know what they have at home,” she said, then tried to puzzle out why that is. “It’s the Prairies, I don’t know, because you’re supposed to look to the sky for the beauty?”

After we left the Barbie glow of the coffee shop, we drove around the city’s downtown core, and Ms. Rollins guided me through the hollowed-out areas surrounding the shelters along Higgins Avenue, all with people lined up outside on a savagely cold night. It’s easy to see why this pocket of downtown, with its haunted moonscape quality, distresses people who don’t have to be there.

If you rank postal codes by median income, Winnipeg is home to three of the 10 poorest, according to data provided by Statistics Canada. It had the second-highest murder rate among Canadian cities (behind Thunder Bay, Ont.) in 2022, and the 52 homicides that happened in Winnipeg last year – 11 more than the year before – helped to give Manitoba the largest homicide rate increase in the country.

So Winnipeg’s challenges are real and heavy. But none of us is only who we are on our hardest day. The counterbalancing side of the ledger to a city’s problems are its helpers, its boosters and the people who willingly invest skin in the game; Winnipeg must surely top those tallies, too.

Kevin Walker, executive director of Bear Clan Patrol, and his group’s volunteers are some of those people. I met them at their headquarters on Selkirk Avenue one evening for their nightly walk around the North End. They’re one of several citizen-run groups that conduct volunteer foot patrols in areas of high crime and poverty.

“Our main goal of Bear Clan is to earn the trust of the community and earn the respect of the community. And how we do that is by being consistent, by being out there,” said Mr. Walker. “We’re out there when nobody else is.”

The group set off along an alley, some carrying Naloxone kits and others yellow sharps containers, while Mr. Walker towed a wagon stocked with bottled water, granola bars and homemade bannock. They shone flashlights around the piles of trash and discarded household items mounded along the laneway like dirty snowbanks. When someone found a needle, they called out, “Pine tree!”

One of the volunteers was Robert Shaw, 66, now retired after a long career at the Canada Revenue Agency. He loves Winnipeg. As in, he volunteers for a free tax filing program that works with marginalized people and created free walking tours of neighbourhoods people otherwise avoid and can tell you the history of just about anything in town – that sort of loves Winnipeg.

“I’m so optimistic right now,” he said. “We’ve had a change in provincial government and I feel like there’s momentum now for a lot of things that haven’t happened. I think that funding and care and knowledge is going to really roll out this time.”

Toward the end of their route that night, Bear Clan encountered a woman on a bike who wasn’t dressed for the weather. One member rooted around in the wagon, then pulled out a donated parka that looked warm and well-made. She helped the woman pull it on, then filled her pockets with snacks, calling her “Sweetheart” before she rode off.

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'I think there’s a lot of significance that there’s a residential school right here, in the heart of Winnipeg,' Manitoba Premier Wab Kinew says of the Assiniboia Residential School.Shannon VanRaes/The Globe and Mail

Premier Wab Kinew, the man leading the change that has many Winnipeggers feeling optimistic, wanted to meet at the site of the former Assiniboia Residential School, one of the few urban residential schools in Canada. In operation from 1958 to 1973, all that remains of it now is a yellow brick classroom building that houses the Canadian Centre for Child Protection.

This was the first of two destinations Mr. Kinew wanted to show me, so he climbed into the driver’s seat of his press secretary’s car, his RCMP detail in the vehicle behind. He began talking before he started driving, his eyes fixed on a distant horizon; these thought pathways were well-travelled in his head.

“I think there’s a lot of significance that there’s a residential school right here, in the heart of Winnipeg, effectively – this is one of the biggest thoroughfares,” the Premier said, gesturing to Academy Road. “And it was in operation within people’s lifetime who live in this neighbourhood.”

River Heights, the genteel and movie-set-beautiful neighbourhood surrounding the school site, is home to Mr. Kinew’s family now, too. The night before the provincial election in October, he and his wife Lisa Monkman, a physician, went for a bike ride and stopped here on the way home.

“We knew what was on the verge of possibly happening the next day. And I just told Lisa, life is hard, but life is beautiful,” Mr. Kinew said. “I really, in a very humble way, am at a loss to explain why it is that somebody like me gets to have the chance that I do.”

After a five-minute drive down Academy Road, we arrived at the other Winnipeg bookend he wanted to show me, still in tony River Heights. He parked across the street from Kelvin High School and then explained why we were there.

Kelvin was here when Assiniboia was open; their hockey teams played against each other. Now, kids from all over the city attend this school, he said, drawn by the international baccalaureate program. Mr. Kinew’s 16-year-old son attends Kelvin, playing on the varsity football and basketball teams; his 18-year-old son, who graduated last spring, was captain of the hockey team.

“So why I wanted to drive you from there to here was to just make the point: That’s where we were a generation ago. There were two schools in this neighbourhood – one for these kids, one for those kids,” the Premier said. “Today, all the kids are going to school together here. You know, I’m bragging about my sons, but at the same time, kids from any walk of life can succeed here. Things like that make me proud of Winnipeg.”

He doesn’t know exactly where we are in the collective journey of reconciliation, he said, only that it is a journey, and the kids at Kelvin are starting it from a very different point than he did. As our conversation wrapped up, Mr. Kinew climbed out of the vehicle to say goodbye before he and his staff raced off to another meeting. But first, he asked if I needed a ride somewhere, because that’s Winnipeg.

I did another interview on the move with Kate Fenske, CEO of Downtown Winnipeg BIZ, which promotes downtown business, culture and revitalization. We met at Modern Electric Lunch, which might be the most appealing coffee shop I’ve ever visited, all glowing blonde wood, exposed old brick and funky lighting surrounding incredible coffee and food.

On the walls, framed in neat rows like museum artifacts, are receipts from the long-gone lunch counter that inspired the name: toast and coffee for $0.20, a hamburger steak for $0.40. The building that houses the restaurant is called the Fortune Block for real estate magnate Mark Fortune, who built up much of Portage Avenue before he went down with the Titanic. The block was close to demolition when a local family of developers bought and painstakingly restored it in 2019.

Ms. Fenske chose to start our walk at Modern Electric Lunch because to her, its loving homage to the past helps conjure downtown Winnipeg’s future. “I love this place because it shows what’s possible,” she said.

We walked toward the mini-Chicago skyline of the banks-and-business part of downtown, then headed down Graham Avenue into the entertainment district.

A man veered across the sidewalk, yelling at the air in front of him. Experiences like that make some people feel unsafe downtown, Ms. Fenske acknowledged, though in the pandemic era, it’s far from unique to Winnipeg. The Downtown Community Safety Partnership, a non-profit that launched in early 2020, sends outreach teams to stroll downtown around the clock and respond to calls when someone needs help rather than police.

We passed through Mottola Grocery, a glorious temple of Italian food, where the owner greeted Ms. Fenske, a friend, and me, a total stranger, both with a hug. We ducked into Cityplace shopping centre to stroll its indoor farmer’s market, where displays of sleek wooden games and handmade jewellery made it clear that Winnipeg artisans are working way, way above the level of crocheted whatevers.

Downtown BIZ is the toughest job Ms. Fenske has ever had. A few years ago, there was real momentum, she said, before the pandemic did to Winnipeg’s downtown what it did to every other city’s. But now, between big-budget plans for major redevelopment projects and the investment and energy of entrepreneurial Winnipeggers who want to hang out their shingles, Ms. Fenske feels more optimistic than she ever has.

“Everyone’s kind of going, ‘This is important, we want to be part of the solution,’” she said. “And right now, for the first time in over 20 years, we actually have three levels of government saying they are committed to working together and that downtown is important.”

Back out on Portage Avenue, Ms. Fenske showed me a former Staples store that had been transformed into the wildly popular Pitikwé Skatepark by a group of community organizations. Across the street, she noticed that a shop had wrapped a broken window like a Christmas present to hide the damage. “Here, put a bow on it,” she said, guffawing appreciatively.

It seemed like a perfectly Winnipeg solution: a pragmatic fix, a creative way to make something beautiful, and a little bit smartass.

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Jerry Daniels is Grand Chief of the Southern Chiefs’ Organization.Shannon VanRaes/The Globe and Mail

A few blocks away, the Hudson’s Bay building that sprawls across an entire city block was in early demolition when Southern Chiefs’ Organization Grand Chief Jerry Daniels showed me around later that day. There was a rushed-apocalypse feeling to the place. Huge white pillars were about the only thing populating the cavernous space, the one nearest us still bearing a sticker inviting people to shop 24/7 on The Bay’s website. High on one wall, black letters steered ghostly shoppers toward disappeared “SUIT SEPARATES” and “SLEEP WEAR.”

The 655,000-square-foot space has been vacant since 2020, when the store closed after the pandemic hastened its long decline. And then in 2022, Hudson’s Bay Co. handed over ownership to SCO, which represents 34 Anishinaabe and Dakota nations in southern Manitoba.

The SCO is planning a $130-million redevelopment – set to reopen for the building’s centenary in 2026 – that will transform the iconic former department store into an Indigenous hub, including 300 affordable housing units, assisted living for First Nations elders, a child care centre, museum, two restaurants and a health and healing centre.

In a few years, this grand old dame of a building – once indelibly linked to the commercial face of colonialism, but now completely reimagined to serve a booming Indigenous population – could be one of the anchors of a revitalized downtown. And in creative-to-the-bone Winnipeg, even economic reconciliation is poetic. The project is called Wehwehneh Bahgahkinahgohn, which means “it is visible.”

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Jerry Daniels, Grand Chief of the Southern Chiefs' Organization, inside the old Hudson’s Bay building in downtown Winnipeg on Nov. 23.Shannon VanRaes/The Globe and Mail

Roughly every third person I talked to insisted that I go eat at Feast. So I asked to meet with executive chef Christa Bruneau-Guenther at the Indigenous restaurant she opened in the multicultural West End nine years ago.

Her shredded bison dip had juicy shards of meat tucked into a double pillow of bannock, along with local cheddar and wild blueberry barbecue sauce, with a ramekin of au jus for dunking. It all carried a delicate sweetness and depth you’d never find in a similar dish at an average pub or restaurant.

To Ms. Bruneau-Guenther, a member of the Peguis First Nation, fusion isn’t the right word. “It’s my food reality. I can’t just go dig a hole and cook it out in the bush because that’s maybe how my ancestors made it,” she said. “Food evolves in any culture. So because there’s such a gap in mine, I don’t know how it would have evolved, so all I’m doing is picking up where things have left off and creating what I know.”

When she opened, there were only a couple of Indigenous restaurants in the country, she said, and Feast was busy from day one because of people’s curiosity. Now it’s firmly established as a restaurant and catering company, and it no longer stands alone as a banner of Indigenous culture in a city with a huge and diverse Indigenous population.

“I think food is one of the most powerful things that bring people together, that really can showcase, highlight – and rejuvenate even – an entire nation,” Ms. Bruneau-Guenther said. “Food is medicine.”

I had to agree, especially after meeting chef Mandel Hitzer at deer + almond, where I ate one of those meals that dreamily pops into your brain about once a week ever afterward. It included goldeneye and whitefish caviar heaped on a crisp, hefty latke and dressed with crème fraîche and maple syrup, and a dessert that answered what would happen if crème brûlée had a one-night stand with a pumpkin spice latte.

“We’re really lucky,” Mr. Hitzer said of the Winnipeg food scene, as we sat at the bar of his perpetually packed Exchange District restaurant. “There’s a blend of so many different cultures that have come here that you can really eat your way around the world, in a beautiful kind of way.”

Indeed, Winnipeg is no white-bread Prairie town. Nearly 14 per cent of Winnipeggers are Indigenous, 24 per cent are immigrants and 26 per cent are visible minorities – diversity stats that are all higher than the Canadian average.

As well as running his restaurant, in 2012, Mr. Hitzer co-founded RAW:almond, a three-week festival of food and architecture that pops up on the city’s frozen rivers – literally on the surface of the ice – each winter, drawing chefs and diners from all over the world.

“It’s a creative hub. We go through these long periods of cold in solitude, which I think in a lot of ways brings us together as a community,” Mr. Hitzer said of the city where he was born and raised. “You gotta depend on your fellow brothers and sisters for support when you need it, and it gets the creative juices flowing.”

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'There’s a great, beautiful quirkiness to Winnipeg that if you’re from here, you get it,' Mayor Scott Gillingham says of his city, seen from 40 storeys up on the 300 Main residential tower.Shannon VanRaes/The Globe and Mail

On my last day in town, I talked to Mayor Scott Gillingham in the sky over downtown. He met me at one of Winnipeg’s newest buildings, a slick residential tower called 300 Main, and we went all the way up to the 40th floor lounge, where we had a panoramic view of the city that was mesmerizing even with naked trees and no snow.

What’s intriguing is that 300 Main is not condos, but rentals, and 10 per cent of the units are designated affordable. Like Ms. Fenske, Mr. Gillingham sees buildings like this as key to revitalizing downtown: Office life is not returning to its pre-COVID self in any city, so drawing more people to live downtown is what will make it feel more lively, appealing and safe.

Ask the Mayor why so many people rip on his city, and he’ll share some thoughts – poverty and crime stats are low-hanging fruit, lots of Canadians have simply never visited – and argue convincingly for why Winnipeg is fantastic. But mostly, he sounds sort of cheerfully unconcerned; maybe people will wise up, or maybe they won’t, but either way, he and his fellow Winnipeggers know what they have.

“There’s a great, beautiful quirkiness to Winnipeg that if you’re from here, you get it,” Mr. Gillingham said. “Whether you’re talking about burgers at Mr. Mikes or being proud to be from the North End, or Ukrainian heritage, or the fact that we don’t have freeways, but we have some streets that change names six times from one end to the other.”

They do; it’s bonkers. And if I hadn’t already fallen head over heels for Winnipeg, a ludicrous intersection known by locals as Confusion Corner would have done it.

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Mr. Gillingham went on at length about the good qualities of people who call Winnipeg home.Shannon VanRaes/The Globe and Mail

Mr. Gillingham has talked to corporate recruiters who tell him they have a hard time getting people to come to Winnipeg, but once they’re in, you can’t get them to leave. It’s a ridiculous cliché to say a city’s greatest asset is its people, he said – but then he couldn’t help himself, raving about how resilient, witty, fun, sarcastic, talented, educated and skilled Winnipeggers are.

But it was that first quality – resilience – that he came back to again and again. Winnipeg has faced big obstacles over and over in its history and scaled them together, whether it was floods or losing the Jets, he said, and through all of the city’s problems, it never abandons hope.

“I cannot count the number of times in this first year of being elected I’ve had people come up to me and say, ‘Look, you know, we’ve got some challenges in Winnipeg, but please let me know what I can do to help,’” Mr. Gillingham said. “It happens more frequently than I could have ever imagined. It’s people of prominence, it’s neighbours, it’s random people in the mall that come up and say that.”

As I got to know Winnipeg, the phrase that kept popping up in my head was, “This city has so much going for it.” Maybe the most important of those things is the way Winnipeggers pull for their hometown, how invested they are, how much of themselves they give to it, how they love their city – and how it loves them back.

There was a moment, as the pandemic stretched on and on, when we talked about people moving back to their hometowns to be closer to their support networks, or big-city Ontarians decamping to Atlantic Canada in search of better quality of life. The reality of those trends was probably never as big as the discussion. But the collective wish fulfilment of that conversation was telling and overdue.

All at once, we seemed to realize something about the value of building the best life each of us could, not just the biggest one.

This feels like something Winnipeggers figured out a long time ago. They were just living there at the forks of their two rivers, making art and food and fun of themselves and each other, until the rest of us caught up.

With a file from Chen Wang and Stephanie Chambers

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