A bike tour of Portland reveals a city with food and community at its heart: ‘You don’t have to conform to belong’

“In Portland, you can be yourself and then find other people that you fit in with,” storyteller Sarah Gilbert declares as we cycle through a covered car park surrounded by huge murals. Intricate Slavic babushka figures in a sunflower field sit beside comic-book-style dog portraits.

This car park was once a burnt-out building that attracted graffiti, but instead of chasing the artists away, Portland has made room for them. As Sarah cycles away, she shouts: “You don’t have to conform to belong.”

Situated in America’s Pacific Northwest, Portland has grown in relative geographic isolation. It has long cultivated an identity built around creativity, independence and community, so successfully that it’s attracted the disdain of the Trump administration. Today, Portland is celebrated for its vibrant culture, food trucks (known locally as carts), independent shops, and one of the largest urban parks in the USA. I’m curious about what makes it feel so different.

It’s why I’ve started my trip with a bike tour of Portland’s Eastside food carts with Sarah, the founder of Around Portland Tours. Our first stop – WonderLove – is a sprawling food cart hub with picnic tables and a three-storey shipping-container bar with a rooftop terrace.

WonderLove is home to one of Sarah’s favourite breakfast carts, Honeycuspe. She explains that during the 2008 financial crisis, empty parking spaces let carts establish themselves permanently, and the “pod” emerged: several carts sharing one space and adding tables, lights and toilets. In 2024, city figures put the total number of carts at more than 500.

Our order arrives – a savoury “Garden of Eros” waffle topped with smashed avocado, fried egg and pumpkin seeds, followed by blueberry orange blossom compote and whipped cream. Every crisp, pillowy bite is pure joy.

Back on our bikes, we cycle to Farmhouse Carts, a smaller community-focused pod where even dogs have a cart. “In other cities there’s competition between businesses, but in Portland it’s more about community than competition,” says Sarah. For example, some pods won’t allow duplicate cuisines, preferring variety over rivalry.

Our final stop is Cartopia, one of the original pods and now a popular late-night spot, where fairy lights, colourful papel picado bunting, and music create a festival-like atmosphere. With the summer heat, I settle for a Portland craft soda – a blend of hibiscus and rhubarb – while plates of poutine, tacos and falafels circulate around me.

Some carts have later become restaurants, but Sarah tells me success has already doubled rents in one pod. I’m left wondering what happens when food-cart culture becomes too successful to remain affordable.

The question follows me to Alberta, a neighbourhood in northeast Portland, where I join Amanda, Sarah’s colleague, for a walking tour along Alberta Street. Amanda tells me how Alberta was a thriving area of Portland’s Black community in the early 20th century until flooding and urban regeneration projects displaced many residents; by the early 1990s, the area was in serious decline.

“People like Rosalyn Hill, an African American businesswoman, were saying, ‘this is our community, and we want to turn it around’,” Amanda says. Hill wanted to prove the street could thrive while retaining Black ownership – encouraging businesses to remove window bars, keeping regular opening times and bringing in art. “Art is often the catalyst for change,” Amanda adds. “And Rosalyn’s success meant she became known as the Queen of Alberta Street.”

That revival became the Alberta Arts District, where murals celebrating Black history cover buildings, and bus stops are sculpted into public art. We amble past the Alberta Cooperative Grocery, Community Cycling Center, and Alberta Street Gallery, and a mural of Black women and children lifting golden blocks marked “community”, “faith” and “power”, towards the words “Building a Legacy”.

Signs are going up for Last Thursday, Alberta’s monthly street festival. “If you want to sell something, you come out here,” says Amanda. “Cookies, artwork or even poems [that you] read on the spot.” It’s the same permissive spirit as the carts – make space and people will join in.

Alberta is now one of Portland’s most fashionable destinations, but as higher-income residents and businesses move in, many of the original residents who revived the area have been priced out. “I know a lot of the people in the neighbourhood who feel like they're being left behind,” Amanda tells me. I ask how Portland can create prosperity without displacing the communities that created it. Amanda’s answer is simple: “The best way forward is to raise everybody up together.”

To round off my time in Portland, I hop aboard the streetcar to Washington Park, a vast, forested hillside of winding trails, public gardens and panoramic city views.

In the Japanese Garden, lemonade light filters through lime-green maple trees onto pink azaleas and purple iris, while a song sparrow sings over the trickle of a waterfall, with snow-capped Mount Hood in the distance.

At the International Rose Test Garden, the roses are in full bloom. A retiree in a sports vest is crouched by the path, a bag of seed in hand, coaxing a rotund squirrel closer. She tells me it's something she enjoys doing most Sundays.

Portland, like so many other cities, wrestles with the tension of becoming more prosperous while remaining a place for people of all incomes to call home.

The woman scatters her last handful of seeds and looks up at the families smelling the flowers and chatting animatedly. “Look at the happiness everyone is sharing,” she says.

Here in Portland, you don’t have to fit in; you just have to show up.

Yvette travelled as a guest of Travel Portland

British Airways operates daily direct flights to Portland, Oregon, taking around 10 hours, with return tickets starting from £481.

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