I'm on a train in Narbonne, France, 60 miles north of Le Perthus and the border with Spain. I've been staring out the window dumb for the last half-hour. The TGV ran past the Étang de Leucate, a spuming lake below the Pyrenees that I'd never heard of until I looked it up on Google Maps. Now we're hugging the Canal du Midi through to Beziers. I'm sure it's getting colder outside as the train heads north to Paris, but it's warm enough on the top deck. I don't need a jacket. The guy across from me is sound asleep, curled up like a coyote in his chair. Ash grey clouds have started to obscure the sun.

I've been listening to Owen Ashworth most of the way. "Christmas in Oakland," from Advance Base's 2012 LP A Shut-In's Prayer, has been on my list for the last two-and-a-half weeks, and I'd roughly traced out its contours already. The Rhodes piano hums and glistens and flickers as though it's coming out of a busted old VHS tape, and Ashworth sings it in a run-down croak. Like most of his songs, in both Advance Base and Casiotone for The Painfully Alone, it's bare-limbed, economical, and graceful, a tiny story in four parts: "It's Christmas in Oakland / I don't feel a thing / Rode bikes to the Chevron / For Chesterfield Kings," he sings, before killing off the first-person altogether. "The smoke in our eyes / As we ride how it stings / What tidings we bring." It is, we find out at the end, a love song, even if it has its caveats: "On Christmas in Oakland / We had a fling / You looked like an angel / Who'd lost its wings / With stars in our eyes / Lying on mattress springs / We were beaming."

That final verse also turns "...Oakland" into one of Ashworth's least brutal holiday songs. His back catalog is peppered with Christmas songs, most of which follow the same format as "Christmas in Oakland" without hinting at that little moment of bliss. In 2015, he gathered all the ones he’d recorded to date onto a 25-minute Christmas Mixtape. It begins with a fluorescent instrumental version of "Hark! The Herald Angels Sing" (which he later reworked into "Harsh The Herald Angels Sing," an agnostic song about a single woman's pregnancy), then moves through the United States, picking up new stories in each hollowed-out town.

There's "Christmas in Dearborn." a muffled, country-tinged song about returning home for the holidays and confronting the familiar: "On the bed where you first slept / With your husband at seventeen / Read your yearbooks back to front / With TV on & your skirt off." On "Traveling Salesman's Young Wife Home Alone on Christmas in Montpelier, VT," a few hundred miles east, he sings through another pregnancy. This time it's a young woman whose husband spends his holidays in motels, leaving their marriage hanging by just a couple of threads: "What are you doing on your own with frozen ears? / I know we're changing like the trees in Montpelier." The exhausted "Cold White Christmas" might be the most isolated of all, a note from a 22-year-old in St. Paul, Minnesota, a city as "bare & as mean as the winter trees." Eventually the tape reaches "Christmas in Milwaukee," its lyrics more ominous and messy than the wide-open major chords would have you believe. "The folks in their graves / Have been doing summersaults," he sings. "I’ve got trouble enough."

"Christmas is such a different experience depending on where in the country you are," Ashworth told The A.V. Club's Randall Colburn five years ago. He's right. How could two Christmases in two different Americas have anything in common besides TV schedules and too much alcohol? Ashworth tends to set his Christmas songs in the bitter cold—only in Oakland is it "warm as spring"—and there's a loneliness that connects them all, but the changes in heart and the decisions made vary wildly from place to place. In Oakland, there are movies and a love affair; in Michigan, "Your mom complains about the tree"; in Milwaukee, "They broke the window / Took the radio & wreath."

This year, Ashworth released "Christmas in Nightmare City," a song that's more autobiographical than the rest, despite the second-person. "Heater’s blowing in the car / Over the sound of a college game / Don’t know the team names / But it’s nice to have a voice on." It is, he explained in a note to Talkhouse, about "the restless energy, sugar cravings, and minor identity crisis" that he experienced after he stopped drinking last year. The song itself came out of a night in Gary, Indiana, another frost-bitten Midwestern city; he'd been driving around to cope with the sober insomnia, and in the midst of the thrum of the factories, he "was struck by the grace of the industrial work lights, twinkling through the mist," he wrote. "They reminded me of Christmas, and I found it all strangely comforting."

Tellingly, he also wrote there about his clutch of songs from Christmas past. "[They] tend to focus on people at low points in their lives," he explained, "people who have found themselves in the midst of relationship crises, difficult life changes, or just bad luck." The voices he's adopted in the past—the mothers-to-be and the desolate, grown-up kids on their way home to the Midwest—were conduits. If there are a million anxious holidays in a million frigid cities, there might be a million "Christmas in…" songs to write, eventually. "The songs are intended to be a comfort for folks going through their own tough times," he wrote. "Commiseration has always been a guiding principle of my songwriting."

This train just pulled out of the station in Montpelier, France. I've always preferred travelling by rail, and I've only ever come up with two reasons why. One: Flying is miserable, and I'm not normally in that much of a hurry to get anywhere. Two: drifting through a country in total silence next to widescreen windows gives me something I can't find anywhere else. You panic and tire and sputter out just about every day, but here, for a little while, at 100 miles-per-hour, you can just stare at industry and water and nickel-colored clouds over acres of nothingness. It's all strangely comforting.

Alex Robert Ross don't feel a thing. Follow him on Twitter.