Whenever I want to reflect on how much Portland has changed since my days as a kid, all I have to do is take a look at my alma mater.

I attended Cheverus High School in the early eighties, and the school was then a very different place. The student body — to take the most obvious example — was made up entirely of boys. My classmates were mainly Irish and Italian kids whose families had grown up in tenements on Munjoy Hill before they earned enough to move off the peninsula to the more suburban streets of Rosemont and the Deerings. There were French kids like me, as well, drawn from the Greater Portland area. Back then you could pay your tuition with the money you earned from your paper route (as I did). Most of the teachers were Jesuits: novices, scholastics, and priests. The campus, overlooking the liquid mirror of Back Cove, was handsome but fairly compact – we had to play our football games a few miles away at Fitzpatrick Stadium, beside Deering Oaks Park.

Today, the Cheverus student body is co-ed, with an almost equal number of boys and girls. The school attracts students from the city, but more and more of them seem to come from the suburbs, and there is an increasing sense of diversity in the halls. The quality of teaching remains first-rate — among the finest educational experiences in the state, in my unbiased opinion — but the Jesuit presence has been greatly reduced. Meanwhile, the campus has expanded gorgeously, and on crisp autumn evenings, drivers on Interstate-295 can see sports lights glowing brightly from across the cove.

Cheverus is hardly a microcosm of the “new” Portland. The changes that have swept through the city are much more extensive, robust, and complex. But in the evolution of my school over three decades, I can feel the dynamism of a city undergoing its own sea change.

Throw a cobblestone these days, and you’ll hit a TV chef recording a segment on Portland’s famed dining scene. Travel writers now routinely gush over our galleries, music halls, and seaside shops. Sociologists tout the city’s livability and the vitality of its creative economy. It’s hard to avoid the sense that, in Portland, Maine’s future has already arrived.

That’s an uneasy idea to some. The rest of Maine has always had a complicated relationship with its largest city, a place that has sometimes seemed too detached, arrogant, and southward-looking. But in this special issue, we’re letting go of our inhibitions and writing the mash note Portland deserves. We’re not embarrassed to admit how much we love the place. Turn to page fifty, and you’ll begin to understand why.

— Paul Doiron