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Take Your Kids Christmas Caroling



We took our kids caroling at a jail, a hospital, and a nursing home last Advent. Not only was it more fun than we imagined, it offered our kids a couple of graced moments that brought home the true meaning of Advent.


by Jerry Windley-Daoust


It’s a stock scene in commercials and greeting cards around this time of year: a cluster of rosy-cheeked carolers, clad in fashionable winter gear, sings Christmas carols at a neighbor’s door while snow falls gently in the warm light that spills from inside.

But how often do you see this scene play out in real life? (The Epic Caroling video at the bottom of this post doesn’t count.) Caroling seems to have fallen out of fashion since the 19th century. I have a few ideas about why this might be the case:

  • It involves singing. Most people don’t think they sing well. They’re right (because they don’t practice).
  • It involves singing in public. (The horror!)
  • In the freezing, wet cold.

So the idea of going caroling is a non-starter for most people, but I’ve always thought it would be fun (despite definitely not having a singing voice). And last year, thanks to a Quaker friend who did all the footwork organizing the event, I finally got my chance to try it out. Naturally, I brought (or, in a couple cases, dragged) my kids along.

And guess what? The experience was not only fun, but marked by moments of real grace . . . the kind of “Christmas magic” that all our Christmas cards and television specials want to give us. That extra “sparkle” wasn’t provided by gently falling snow on a made-up television set, but by three very different settings: a jail; a nursing home; and a hospital.

The choice of those locations turned what might have been just another holiday get-together into works of mercy—specifically, visiting the prisoner and caring for the sick.

We started the evening by meeting up at our Quaker friend’s house, where about half as many people as expected showed up, maybe for the reasons I listed above, or maybe because the weather wasn’t ideal (cold, windy, and snowing hard). We were quickly introduced to our fellow carolers and received well-worn, homemade booklets of Christmas carols. Then we headed out to our first destination, a Catholic nursing home, without so much as a single practice session.

The nursing home staff were more than happy to usher us to three different floors, including the locked-down Alzheimer’s unit. On each floor, the staff rounded up any residents who wanted to hear our caroling, and we dove right in—still in our wet coats and hats, and still without having practiced a single song. This led to a few false starts and some good-natured arguing about pitch between the two or three people who had any music experience whatsoever, but the residents didn’t seem to mind. They smiled, clapped, and joined in, if they could. We even took requests, since we had no planned program.

Encouraged by the warm response of the residents, all my kids got into the spirit of the evening pretty quickly—even the shy and easily embarrassed teens. The two youngest boys, ages six and nine, sang with more enthusiasm than anyone—especially the nine-year-old, who is mentally and physically disabled. On the car ride to the next destination, they asked some questions and discussed the situation of the residents, but otherwise seemed pretty unfazed.

The next destination was the county jail where, unfortunately, the kids weren’t allowed beyond the lobby. The rest of us followed a couple of sheriff’s deputies back to the holding area, which consisted of two long hallways, one for the men and one for the women, lined with closed and locked doors. The hallways were as bland as any you might find at a university, or your doctor’s clinic—maybe blander, since they were completely unadorned.

The deputies opened a security door at the head of each hallway and had us stand just outside. We couldn’t see the prisoners, and they couldn’t see us, so our leader introduced us (shouting, you know) and asked for requests. A couple of guys shouted requests back, and we sang as loudly as we could:

Why lies he in such mean estate,
Where ox and ass are feeding?
Good Christians, fear, for sinners here
The silent Word is pleading.
Nails, spear shall pierce Him through,
The cross be borne for me, for you.
Hail, hail the Word made flesh,
The Babe, the Son of Mary.

And we sang:

Angels we have heard on high
Sweetly singing o’er the plain
And the mountains in reply
Echoing their joyous strain.

Next we were escorted to the basement recreation room, where a good-sized group of men in bright orange uniforms were finishing up some kind of 12-step meeting. We didn’t actually enter the room; again, we were kept in the hallway, behind a line marked on the floor with tape, and the prisoners likewise kept a respectful distance.

It was both awkward and moving; awkward, because not only would these men not be enjoying Christmas with friends and family, but because those orange jumpsuits made their humiliation so glaringly obvious. I mean, what can you say, by way of farewell? “Have a merry Christmas . . . in jail . . . in your orange jumpsuits”? But it was moving, too; some of those lyrics take on new meaning inside a jail: “Mild He lays His glory by / Born that man no more may die / Born to raise the sons of earth / Born to give them second birth.”

Our final destination was a local hospital; again, the volunteer coordinator met us and showed us to the areas where we could sing. Mostly we sang in the hallways, with the idea that the patients would hear us from their beds. But a woman visiting her mother ushered us into her mother’s room; she requested several songs (including one from her childhood that we didn’t know), and she sat up in bed listening, holding her daughter’s hands, and singing along when she could—and shedding quiet tears. (Of happiness, I presume—although maybe she was a former choir teacher who was just too polite to critique our singing.)



All three stops took about two hours, after which we hit a local coffee shop that provided free hot chocolate for everyone. It was welcome, because we all had sore feet and somewhat hoarse voices. But I also noticed that everyone (even the six-year-old!) was all smiles and laughter . . . and what better Advent decoration is there than that?


Tips for Planning Your Own Caroling Party

As our experience demonstrates, a caroling party doesn’t need to be a lot of work. If caroling is something you’d like to try with your kids, here are a few things to consider.

Plan ahead. Set a date a few weeks in advance, especially if you plan to carol at local institutions. Even if you decide to just go around the neighborhood, though, you’ll want to settle on a date and get the word out early.

Carol indoors, or be flexible. The weather outside was “frightful” on the day we went caroling—there’s no doubt we’d have cancelled if we’d been caroling outside. If you live in an area prone to bad winter weather, stay indoors or think about backup plans.

You don’t need a big group. Contrary to the Improv Everywhere video at the bottom of this page, you don’t need a 20-piece brass jazz band. (Although that would be something!) Get on Facebook, call a few friends, or drop an announcement at your parish. Our group probably had fewer than a dozen people total, including kids, and it worked out fine.

Choose music that everyone can sing. Unless you’re part of a choir, when you make up your song booklet, choose music everyone can easily sing. Most of the old standards are great, but a few (“O Holy Night” comes to mind) are just too tough for unpracticed amateurs to do well. Skip ‘em. And make sure to include a few songs that your littlest ones will know.

There are many Christmas caroling songbooks available, but the gold standard remains The Christmas Caroling Songbook by the Hal Leonard Company [Amazon].

Hook up with local institutions. It worked great for our group to visit the local nursing home, hospital, and jail, but that doesn’t exhaust the possibilities. Consider asking your pastor for a list of homebound parishioners that he visits on a regular basis, and arrange to go caroling at some of their homes. Homeless shelters, soup kitchens, government centers, and military bases are other possibilities. You’ll need to contact the appropriate authorities well in advance to make arrangements the first year, but if you make it a regular tradition, it will be easier the second time around.

Practice your fa-la-la-la. Our group deployed without so much as a practice, but your group might be more comfortable practicing a little in advance. You can either meet a few days in advance to polish your program, or just send people the music ahead of time so they can practice on their own. If you plan to practice right before going out, keep it really short so that little ones don’t get cranky too early (and adult voices don’t give out before you’re done).


Learn more

As you might expect, Wikipedia has an exhaustive history of the Christmas carol that you might find interesting.

And here’s a standard to shoot for: Epic Christmas Caroling! Erm, if you have a corporate sponsor and access to professional musicians. Enjoy!

Follow Jerry Windley-Daoust:

Publisher, Gracewatch Media

Jerry Windley-Daoust is a writer, editor, and father of five. He writes essays and stories at Windhovering and is the show-runner for Gracewatch Media, a small Catholic publisher. You can follow his latest publishing projects at gracewatch.org.

  1. kielersnyder@gmail.com'
    Angela Snyder
    | Reply

    The big kids and I were invited to carol this year with a group that has shown up at our door since we moved. I recall the first time the rang our bell in the dark of night that I had never had carolers sing to me. It really is such a beautiful thing. The kids were honored to be invited this year. They LOVED it!

    Also, that video is epic! Wow!

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