My wife, Vee, is from Arizona—but she hasn’t seen a lot of it. So on a recent trip to Tucson, we decided to drive down for a 24-ish-hour stint in Bisbee, a mountain town that revels in its chipping painted buildings, colourful retired-boomer aesthetic, rugged idiosyncrasies and self-indulgent quirkiness. It feels a little put-on—which is ironic, given how the whole town seems to have grown quite organically, in a scrappy, ad hoc way. The infrastructure almost seems ramshackle by design, with narrow curving roads and slender sidewalks snaking between the hills.

To be clear, I love a mountain town. The adventures we took in Korea, itself a nation that is 70 per cent mountainous, remain some of my favourite, whether they were ill-advised snow treks or intimidating steep inclines. But we were in our 20s then, childless wanderers in search of new landscapes and survivable challenges.

After our son was born, and saving money became a priority, the wild tales cooled down. Bisbee was something of a return to our earlier form—albeit a very, very relaxed version—by virtue of its sheer distinctness.

But I can tell you, Bisbee feels like an older person’s adventure. I was not surprised to discover their median age was 43, fully five years higher than the state average of 37. Nor that the population has been in steady decline since the 1970s. Credit to those who stay: it takes effort to live there.

We pulled into the Jonquil Motel, a 1930s structure on the cheaper side of town (outside the fancier, cleaner downtown core), without many expectations. A middle-aged couple in expensive cycling gear checked in ahead of us. When they finished, the man at reception gave me a friendly and comprehensive spiel about what was nearby (a Circle K) and which direction everything was (east—down the only main road there is). The rooms were clean enough, with interesting shower tiles and well-used furnishings, but we hadn’t considered the size before springing open our pack-and-play—we wound up pushing our bed as close as possible to the bathroom to make space for our son to sleep not within three feet of the old radiator.

I shouldn’t pretend like we did a lot of research before driving down. We wanted to wing it. So we ended up strolling along the roads, breathing in the fresh mountain air, appreciating the bountiful street art and brightly colored century homes.

The whole area’s vibe is beyond vintage—it should feel, somewhat, like you’re travelling back in time. Grand old hotels, classical breweries and offices, and a bevy of heritage signs (“Welcome First United Methodist Church, Since 1888”) make this evident. The biggest nearby tourist attraction is Lowell, whose main drag, Erie Street, is a ghost town, vacated after the nearby mine closed down and the population collapsed. The region leans into this as a draw, parking dead classic cars and buses on the street for decorations. The crumbling infrastructure matches, with its broken sidewalks, cracked roads.

To be clear, I liked Bisbee. A lot. I liked the laid-back attitude, the beautiful vistas, the nearby hikes we didn’t get a chance to try. I’d be happy to come back. But it’s not a family destination. There are barely sidewalks to walk a stroller. The lone playground we found, on a hill near downtown, attached to the town square, was vacant and poorly maintained. The view from the park was a graffiti-covered, dilapidated wall from an unfinished demolition project.

And maybe you’re thinking: so what? It’s an older person’s getaway. Creative, active and historic. I’d agree with all that. What I wanted was to wake up to the sun rising over the mountains, to get a little exercise among the desert foliage. And I did—trudging my kid in his stroller up and downhill to get him to sleep, I thought, you know what? It’s no mountain hike, but it’s a trek.