Kenyon Ross just wanted to make some extra money at Christmas. He was a singer. He knew other singers. People liked holiday music. It was pretty straightforward: get a few friends together, wear something festive, sing at office parties, and pass the hat. That first year, it was all local—just Birmingham, Alabama. They’d pile into a car with scarves and pitch pipes, show up at a party, sing “We Wish You a Merry Christmas”, and move on to the next one. No website. No booking form. Just singing.
It worked. The gigs kept coming. People started calling the next year, and the year after that. Eventually Kenyon realized he had something more than a seasonal side hustle. He bought nicer costumes. Rehearsed more. Said no to anyone who couldn’t hold a harmony. He started calling the group The Christmas Carolers, which sounded more official than Kenyon and Friends with Santa Hats.
How It Works Now
These days, if you book The Christmas Carolers, here’s what you get: four singers, dressed like they stepped out of a Dickens novel, singing a cappella Christmas music in tight harmony. Top hats, bonnets, velvet capes, the whole thing. They’ll show up at your holiday party or corporate event, sing carols in a corner or walk around the room like wandering minstrels, and leave your guests wondering how they just time-traveled into a Charles Dickens fever dream.
Most people book them for corporate events—lobby performances, holiday lunches, tree lightings, client parties. But they’ve also sung at malls, neighborhood block parties, museums, and in more than one dentist’s office. One group once sang carols while riding a moving escalator. Another group was booked to sing outside but had to compete with a leaf blower. The job changes every time.
What They Sing (And What They Wear)
The setlist is mostly the classics. Deck the Halls, Joy to the World, Silent Night, Carol of the Bells. There’s no piano or backing track—just voices, arranged in soprano, alto, tenor, and bass. It sounds like an old choir recording, but it’s happening live, six feet from your punch bowl.
The costumes are old-fashioned on purpose. Full Victorian. Ruffled collars. Brocade vests. Gloves. They carry little songbooks that are more for show than necessity—most of them know the entire setlist cold by mid-November. Every city’s costumes are slightly different, but the idea’s the same: look like you’re from the 1800s and sound like you’ve been practicing since October.
How They Find the Singers
They audition. Every city has a City Director—usually a performer or voice teacher who knows their local scene—who helps find, train, and schedule singers. Some of them are musical theatre grads. Some sing in opera choruses. Some are choral singers who get way too excited about clean diction and blended vowels. What they all have in common is they can stay in tune and not forget lyrics when someone walks by in a Santa hat and waves.
Once they’re hired, they rehearse as a group until the harmonies are tight and the timing clicks. Everyone learns the same arrangements. Every quartet has to be able to do the full set, without warmup, in a noisy room, possibly with a small child yelling “Jingle Bells!” at them mid-verse.
Where They Sing
They started in Birmingham. Then came Atlanta. Then Dallas. Then more cities. Now they operate in over 20 places across the country—Los Angeles, New York, Miami, Chicago, Houston, Nashville, Denver, and a bunch more. Some cities do a couple dozen gigs a season. Some do over a hundred. December gets busy.
Each city runs a bit like a franchise, but looser. There’s a central admin team that coordinates logistics—Jessica Harris leads a lot of that now—and then local teams who handle costumes, rehearsals, call times, and making sure no one shows up with a cold and tries to fake their way through Hark the Herald.
The singers are seasonal. The company is year-round. Between January and August, the main team works on things like scheduling, marketing, website updates, hiring, and sewing. Then fall hits, and it’s full tilt: costumes need mending, new quartets need building, and someone needs to chase down that one bass who forgot his vest again.
The People Running It
Kenyon Ross is still in charge. He’s been running this thing for almost thirty years, and he still talks about it like a guy who can’t believe this many people want to pay money to hear “O Come All Ye Faithful” at 2:00 on a Tuesday. He doesn’t perform anymore, but he handles a lot of the behind-the-scenes—selecting new cities, keeping the song arrangements sharp, deciding which costume supplier to use when velvet goes out of stock.
Jessica Harris handles sales and partnerships. She works with all the City Directors and makes sure clients know how to book, what to expect, and how many carolers will fit in a freight elevator. She’s the one who smooths over any last-minute chaos, handles group inquiries, and keeps the whole multi-city operation from melting down in the final week before Christmas.
Together, they run a business that exists for about five weeks out of the year, and somehow never really stops. The bookings start in September. The planning starts in July. The rehearsals start in October. The costumes come out of storage in November. And by the time Christmas Eve rolls around, hundreds of singers have wandered through lobbies and courtyards and crowded rooms, singing the same songs people have been humming for generations.
