West-coast cool in and around Portland, Oregon

It's a four-hour flight from Dallas Fort Worth ­International Airport to Portland's PDX, and the young woman sitting next to me on the Spirit Airlines service embodies the familiar flight of "different" people to the trendy West Coast. "Do you live in Portland?" I ask. "From today I do. I'm moving there now. Cool, isn't it?"

“You’re moving there and you’ve never been there?” “Nope.” Did she not think to go there first? “I don’t know. Save on a trip. I’ve Skyped with my new flatmate from Craigslist.” She asks me what kind of music I like, before handing me one of her headphones, connected to iTunes on an old laptop; it’s from the 1990s. After a few polite minutes, I hand it back. If nothing else, the brilliant IFC series Portlandia, with its opening song lines – “The dream of the 90s is alive in Portland” – has prepared me for times such as this.

And also for moments such as this at the Ace Hotel, the HQ of the hipster hotel group with the feel of a Victorian boarding house. A friend meets me in the lobby, and asks a seemingly intellectual-­looking man sitting nearby if he can take our photo. The man, who had looked nice, visibly recoils, before saying witheringly: "Oh, I don't do... ­photos. But I'm sure one of the nice people here will take a picture for you." "Do you think you're too cool to take photos?" I say; he looks surprised. "Why do you think they built this place?" my friend adds. The man retreats back into his newspaper, then disappears.

On a Best of Portland ­Walking Tour, my guide is Alexis, a ­Washington State native who has been here 10 years. She also teaches Zumba and is a cabaret dancer. "This feels like the right place for me right now. Not forever, but for a while," she says. Judging by the large number of homeless people on the streets, she's not the only one. Alexis whips through a bit of ­background on Portland's past as a Union Pacific Railroad town to its present-day exports of apparel (it's the home of Nike), technology and wheat, and the current trend of city-centre food carts (there are more than 600, though quality varies. There's no sales tax and it's "the least-­churchgoing city in the US".

We make a stop at the ­Portland Building, home of the ­Portlandia statue, which is inspired by the city's seal and is the second-­largest hammered copper statue in the country, after the Statue of Liberty. We then pass the Heathman Hotel, a 1920s structure that's mentioned in 50 Shades of Grey and sits next to the distinctive Arlene Schnitzer Concert Hall. I have already spent two hours in the nearby Portland Art Museum, which has an interesting collection of native American art, including stone sculptures from the nearby Columbia Valley, and a surprising collection of Iranian ceramics. Alexis says that the two most-­visited attractions in town are Voodoo Doughnut, a doughnut shop that featured on Anthony ­Bourdain's travel show No ­Reservations; and Powell's City of Books, a great bookshop that I visit separately.

The most interesting part of the tour relates to the city’s boom years in the 1900s, when it was a hub for the timber trade and one of the fastest-growing cities in the United States. “Portland is known as Stumptown because of all the trees that were cut down”, says Alexis. “The Oregon Trail came along the Columbia River with otter fur and other commodities sent to Russia by ship.”

After the city staged its first and only world’s fair with the 1905 Lewis and Clark Exposition, ­Alexis says, “Portland tripled in size. Seattle was 30 years behind.” Now, again, the population of the entire Northwest Coast is growing fast and is expected to double or triple in the next few decades.

“Capitalism brought us a more walkable city,” Alexis continues, describing how in 1845, ­Portland’s small downtown grid system was developed by ­Thomas Brown because of its proximity to the Willamette River. “The blocks are only 200 feet by 200 feet, giving us more corners and smaller streets.” Many of the brick buildings’ cast-iron frames – an anti-fire measure – are still visible, and hold up favourably against the bland 1980s business district.

I’m keen to explore areas outside the city, so I take off the next day in a car rented via an informal car-share service with my guide Heidi, who was born in South Carolina, grew up in Wyoming, has mixed European ancestry and moved to Oregon in 2002. A keen mountain biker, Heidi says that despite the Northwest’s famously wet weather, “we recreate all year round; you just have to plan for being wet for part of it.”

Fortunately, the day ahead of us is dry and sunny, and the peak of Mount Hood, a dormant volcano, is clearly visible. There seems to be little traffic in Portland, and the wide road bridges invite escape. It takes less than an hour to get to the scenic southern foothills, and we stop for a short walk in the Mount Hood National Forest from the Wildwood Recreation Site. The old-growth maple, fir and cedar trees are covered in luminous green moss, and a bridge crosses the Salmon River. I gulp in as much of the clean, clear air as I can before it's time to carry on to take in the view from the Timberline Lodge, a National Historic Landmark that lies on the Pacific Crest Trail, the long-distance hiking route made famous in Cheryl Strayed's novel Wild. "We're the grandest stop from Mexico to Canada," says a staff member. If the mere sight of hundreds of square kilometres of thick pine forest and hanging lakes, all the way to the Cascade Range in the south, is uplifting, it's obvious that an extended hike here would work wonders.

Driving north, we descend through the forest and part of the Hood River County Fruit Loop, a 50-kilometre guided tour route past pear, cherry and apple orchards. To soak in a fraction of the bucolic atmosphere, we stop at Draper Girls Country Farm and buy some fresh, unpasteurised apple juice and a bag of peaches. Then it's down to the small town of Hood River on the Columbia River, before driving along the Historic Columbia River Highway, stopping at the Bridge of the Gods, Multnomah Falls and Bridal Veil Falls.

The great thing about these attractions is that they can all be stops on a whirlwind tour, or the starting point for walks into the wilderness. Sadly, ours is the former, though we also manage a stop at Eastwind Drive-In, a great retro soft-serve ice cream cafe at Cascade Locks. We watch the sunset at Vista House, a 1917 travellers' rest stop with a spectacular view of the vast river valley, before the slow return to civilisation – the scenic farmsteads in Corbett and Springdale look idyllic as we pass by.

Our final stop is at the Black Rabbit Restaurant & Bar, in an old poorhouse in Troutdale. Organic salads, hamachi ceviche, free-range roast chicken and local grilled salmon finish off a day trip that has taken me from urban geeks to trout-fishing hillbillies – and I'm converted. We slip back into Portland from the east, cruising the arty, low-rise residential districts clustered around the streets of Alberta, Hawthorne and Mississippi. I look at property prices and think: Yes, I could live here, too.