How to Start Christmas Caroling for the First Time

The season of joy is here, and we all need as much holiday magic as the world will provide right now. Whether you’re a diehard Christmas fanatic—or you’re just happy to have a few days off work—this series will help you pick the perfect presents, playlists, meals, and activities to make this Christmas the Best Christmas Ever.

This one year when I was in high school, I was hanging out with some friends at a Christmas Eve party and we thought it would be funny to go Christmas caroling. It was a smartass move, a goof, but we walked to a random house in my friend’s suburban neighborhood, someone dared someone to ring the doorbell, and before long a suspicious old man was looking at us like, “well?” 

Our bluff called, my scruffy friends and I started bellowing “Jingle Bells.” It didn’t sound good, but even though we meant it as “aren’t we so ironic?” thing to do on a bored Christmas break, that’s not how it turned out. The old man called his wife over to the doorway, and they were surprised and delighted. So was I. It was an unexpected connection between strangers in a cold world. I still think Christmas is super cheesy, but this wasn’t. It stuck with me. In years since (when I have the energy, anyway) I try to get some caroling together for Christmas. I think you should too.

The history of Christmas caroling

There’s no historical starting point for “people singing songs to each other just because,” but Christmas caroling as a specific thing has historical roots in the wandering minstrels of the medieval times. They evolved into the Christmas choral tradition of the Victorian era, the golden age of the Christmas carol. The Victorians loved gathering family and friends and hitting the streets for some good, old fashioned wassailing. What else were you going to do during the winter in that pre-television, pre-everything era? 

Why you should go caroling

Other than an occasional group of professional carolers at the mall, you don’t see many people engaging in the practice any more. Television, home heating, cars, computers— basically, modernity—killed caroling. We don’t have a lot of space for spontaneous community interactions like Christmas caroling anymore. Here are only some of the reasons I think you should Christmas carol this year:

Breaking social barriers: Caroling provides a rare, socially acceptable way to approach strangers and create moments of happiness. Caroling reconnects us with our neighbors in a meaningful, only mildly intrusive way.

Personal growth: It takes real courage to step outside your comfort zone and sing in public. Who doesn’t need an occasional test of bravery?

For the kids: Your children will remember the year that Mom made everyone go Christmas caroling more vividly than whatever they’re streaming, I promise.

Spreading happiness: A little singing can transform someone’s entire day, especially those who might be lonely or isolated, and isn’t that what this whole Christmas thing is supposed to be for?

How to carol

Christmas caroling goes better with a little preparation. Here’s how to set up an evening of door-to-door holiday cheer.

Step one: Gather the squad

Showing up alone on someone’s porch solo and yelling “Jingle Bells” isn’t caroling, it’s disturbing the peace. You have to get some friends together. You could haunt your local city’s subreddit or Next Door and advertise for people who want to sing, but respondents would probably expect you’re trying to organize a “serious” group. We’re going for the classic, semi-impromptu caroling experience and that starts with a caroling party. Invite friends, family, and acquaintances to a holiday party. Keep it casual, but make sure you’re clear that Christmas caroling will be part of the evening.

Ask your guests to each bring a Christmas sweater, festive scarf, or other piece of holiday costuming. This is important: Something as simple as a festive hat is a visual cue that transforms a group from suspicious to friendly in people’s minds. If you want to be extra, have some LED candles on hand to give out for the caroling. And definitely print out the lyrics of your chosen songs. 

Step two: Choose some songs

Christmas caroling is an anachronism, so it pairs better with older songs. Keep your “set list” to “everyone knows ‘em” holiday classics that are easy to sing. My picks:

“We Wish You a Merry Christmas.” This is the ultimate Christmas carol banger. Energetic, joyous, and easy to sing, “We Wish you a Merry Christmas” is even about Christmas caroling. I wouldn’t follow through on the song’s promise (threat?) to sing until you get some “figgy pudding.” 

“Silent Night.” This classic is slow, pretty, and immediately recognizable to all. It takes a little vocal range to sing correctly, but we’re not going for perfection, so don’t sweat it. 

“Jingle Bells.” This is the easiest Christmas song to sing. It’s maybe a little too easy, but you get extra points if you add in the parody lyrics about how Batman smells.

“Deck the Halls.” Another Victorian-era tune, this one barely even has lyrics to remember: Most of the song is “fa la la la la,” and who doesn’t love singing “fa la la la la?”

Step three: Rehearse

Once everyone is together, run through your songs. Only do this once, and don’t worry about how it sounds. You’re not rehearsing as much as making everyone feels comfortable with singing in a group. If you happen to have some singers in the group though, putting together some harmonies makes caroling magical. 

Step four: Get out there

This is the big moment—the test of courage. Announce to the party that the caroling is commencing, but give your shy guests an out by letting them know that they can come along and just watch if they’d like. (They’ll probably want to join in the end.)

While you could visit some neighbors you know, or even let them know beforehand that you’re stopping by to sing, I’m more in favor of showing up to strangers’ houses with no warning. This increases the chance for both unexpected magic and awkwardness. Both of which are good results.

The classic move is to ring the doorbell/knock, and start singing. This gives your audience the option of not opening the door if they don’t want to deal with you. 

If you like the idea of caroling, but don’t like the idea of strangers and surprise, consider caroling at an assisted-living facility. I guarantee they’ll welcome you with open arms, and the residents will enjoy it. 

How to keep Christmas caroling fun

Here are a few things to keep in mind to make sure your caroling experience stays fun for everyone:

Don’t be too ambitious: Don’t plan a long expedition with multiple stops. Your guests will likely tire of singing for strangers before too long, so only plan on three or four house visits.

Don’t overstay your welcome: A bunch of strangers showing up and singing “God Rest Ye Merry Gentleman” is fun, but only for a few minutes, so don’t perform more than one song unless asked. 

Don’t take rejection personally: When you knock at a stranger’s door, their first reaction is likely to be “What do you want?”  Some people don’t like strangers showing up and singing at all, and some people’s literally don’t know how to react, so don’t take it personally. Try to read the mood and bow out after the first chorus if you run into someone who is really not into it. 

Do nothing but carol: Asking for nothing in return is the most important caroling rule. Don’t mention your church. Don’t try to sell anything. Don’t ask for donations or for anyone to sign a petition. Despite the lyrics to the song, do not demand figgy pudding and threaten to stay until you get some. Just sing “We Wish You a Merry Christmas,” wait for the audience to say, “Wow! Thanks, I guess,” and be on your way.

Be ready to take on new members: Sometimes people you don’t want to know will want to come with you. Let them!