Those luddites among us who still subject themselves to the grueling gauntlet of Christmas shopping in brick and mortar stores are well aware that from Black Friday through Dec. 24, the local mall is some kind of fresh hell.

For a lifelong music fan, a longtime musician and a professional cultural critic, it’s more than the horrifically log-jammed parking garages, the heaving mass of humanity clogging the claustrophobic corridor or the unreasonably long lines. The worst part of the entire experience is the sounds that rain down from the overhead speakers.

There are exceptions, of course. I always count myself lucky to be sprinkled with the light plunking of Vince Guaraldi’s iconic soundtrack to A Charlie Brown Christmas; and novelty tracks, like “Grandma Got Run Over by a Reindeer” can be good for a laugh. But the bulk of popular Christmas music is incredibly grating—polished to a saccharine sheen and jingling with incessant sleigh bells. No disrespect to Sir Paul, but “Wonderful Christmastime” is way too upbeat.

Great pop tunes have the power to uplift while simultaneously conjuring more somber memories. And the best Christmas songs are no different.

Consider “The Little Drummer Boy.” There are certainly some obnoxious arrangements of this song, but the song itself often inspires more powerful performances, because it is inherently a tale of humbling oneself in the face of something greater. “I am a poor boy, too,” the song’s narrator intones. “I have no gift to bring that’s fit to give a king.” Whether you believe in virgin births or child messiahs, the sentiment is still moving.

And and then there’s “Have Yourself a Merry Little Christmas,” a truly blue holiday tune if there ever was one. Written in 1941—at a time when fascism was on the rise in Europe and the world seemed to be on the brink of collapse—the original lyric sheet began, “Have yourself a merry little Christmas, it may be your last.” Frank Sinatra reworked the words for his famous rendition, but an understanding of where the tune comes from allows the listener to hear the song as a brave smile bracing against pain and hardship.

The holidays are a time for celebrating friends and family, sure. But they are also a time for remembering those who are no longer with us. The short, dully lit days, give way to long, dark nights. It’s no wonder we’ve reserved this time of year for three consecutive days of feasting and revelry. It’s all that we can really do to keep our spirits bright.

One of my favorite collections of Christmas tunes can be found on Windham Hill’s A Winter’s Solstice series. Between 1985 and 2005, the Palo Alto-spawned new age record label released more than 20 installments of moody instrumental music under the Winder’s Solstice banner. Some of the songs are recognizable Christmas standards, while others are chilly, solo piano arrangements or sparse acoustic guitar meditations. All of it is unmistakably wintry—the perfect sonic pairing for a hearty cocktail and warm hearth.

I have many fond, dreamy memories of listening to these compositions, bundled up on the couch in my childhood home. I also remember the covers of the albums—all of them snowy snapshots of rural landscapes. One stands out in particular: a dark house rises at the end of a long icy drive; the brittle, leafless branches of the trees and brush reach out to a low-slung winter sun; all is gray and black and white.

But inside the cardboard sleeve, the compositions pressed onto the vinyl disc weren’t as dreary as the record’s cover might have one believe. These songs are as much stark contemplations of wintertime, as they are promises that spring will come again. The series is called A Winter’s Solstice, after all. That old maxim—“It’s always darkest before the dawn”—is never more true than it is on Dec. 21.

Windham Hill founder and Grammy-winning guitarist Will Ackerman joins with fiddler and pianist Barbara Higbie; guitarists Alex de Grassi and Todd Boston; and cellist Ellen Sanders, at Montalvo Arts Center this Sunday to play selections from the Winter’s Solstice series.

Windham Hill: Winter Solstice 30th Anniversary Concert
Dec 17, 3pm & 7pm, Sold Out
Carriage House Theatre, Montalvo Arts Center
Waiting List: montalvoarts.org

Forty years ago, the Palo Alto-raised, Stanford-educated Will Ackerman would often play his guitar for passersby under an archway at the Old Union building on campus, where the acoustics were just right.

“I never meant to draw an audience, but when I would open my eyes I’d find that four, then 15, then 30, then 100 people would be listening,” he says.

Ackerman dropped out of Stanford in the spring of his senior year and became an apprentice carpenter and contractor, but he kept up with the guitar, and went on to form the acclaimed Windham Hill (named after Ackerman’s favorite place in Vermont) record label. On Dec. 12, Ackerman returns to Stanford, along with Windham Hill alumni guitarist Alex De Grassi and multi-instrumentalist Barbara Higbie, plus Todd Boston, for a concert celebrating Windham Hill’s 40th anniversary.

In addition to being an anniversary show, and reunion of sorts, the concert also ties into the holiday season. Known for releasing acoustic—and eventually electronic—instrumental music, one of Windham Hill’s most popular titles is the A Winter’s Solstice series of seasonal music.

“I felt the world desperately needed something that more metaphorically conveyed the season without falling back into the 10,000th rendition of Jingle Bells,” Ackerman says of the collection’s origins. Though all of the Solstice works were distinctly wintery in character, many selections were secular. “I think I was right.”

Looking back on his decades in the business, Ackerman says he always saw music as something he did out of love, not as a career goal.

“While I’d never entertained the notion of doing anything professionally with music, it was always an important part of my life,” he says. In 1976 he released his first record, The Search for the Turtle’s Navel.

“My sole ambition in 1976 was to sell the 300 copies of Turtle’s Navel I had pressed. I expected to have 137 of those in my closet for the rest of my life,” he says.

“A neighborhood childhood friend who happened to be doing promotion for Atlantic Records at the time sent a few copies of Will’s first recording out to radio—the golden days of free-form FM radio±—and the response was amazing,” Ackerman’s cousin and Windham Hill label mate, Alex De Grassi, says. “Suddenly there was a demand, and Will turned to me and said, ‘Let’s record your solo guitar pieces as well.’ Windham Hill quickly morphed into a record label, and suddenly we were both being offered real gigs playing concerts.”

The indie label rose to prominence with its eclectic catalogue of releases falling under the umbrellas of folk, new age, world and more. In the 1980s and ’90s, releases from Windham Hill appeared on the Billboard Chart, including pianist George Winston’s platinum-selling seasonal albums Autumn, December, and Winter into Spring.

“I am given credit as a visionary, but I was just a guy following his heart and, apparently, the bold direction of just following my heart touched a lot of people in nations around the world,” Ackerman says of his label’s success.

For a son of a Stanford English professor, Palo Alto was “a pretty idyllic place to grow up,” he says, recalling his youth spent in the sleepy College Terrace neighborhood. But, “If Stanford influenced me in any way creatively I would say it was in making it clear to me that I was not destined to be an academic, as I and my family had tacitly assumed.”

De Grassi also grew up in Palo Alto, with many fond memories of the area.

“There was definitely something about ‘fingerpicking’ guitar in the air at that time on the Peninsula, as I personally knew and hung out with others more or less my age who were gravitating towards learning to play intricate acoustic guitar music,” he says. He’s looking forward to playing at Stanford again after many years.

“I played one of my very first ‘concerts’ as a recording artist at the Tresidder Memorial Union back in ’78 or ’79,” he says. “I was so nervous; I remember getting halfway through one of my compositions and I blanked out, totally forgot how it went, then immediately tore into the next piece. It all ended on a good note, but it was one of those pivotal moments in my career as a performer. I’ve come along way since those days.”

Ackerman, too, is happy to return to the place that loomed large in his formative years. “Stanford will always have a special place in my heart,” he says, “though I suspect Stanford doesn’t hold me in much esteem as a student.”

Ackerman doesn’t perform live much anymore, as he mainly concentrates on producing records for other artists from his Vermont studio. He says audiences at the Dec. 12 show can expect “to hear a guitar player who is now 66 years old, who has a ton of fond memories of the early days of my own guitar work and the founding of Windham Hill Records. He is not all that well rehearsed these days, but promises to play his heart out and is very much looking forward to this concert.”

A Windham Hill Winter Solstice plays on Dec 12, 7:30pm for $38-$73 at Bing Concert Hall, Stanford.