When Randy Said, “We Should Go Caroling This Year” Finding Hope After Loss — Part 3
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It Started at the Dinner Table
Finding Hope After Loss — Part 3
The caroling years began with one perfect night.
It was November 2005, and we were all out to dinner at Chapin’s in Morris, Illinois — the Dittmer’s, Diss’s, and us Graham's— celebrating Shelly's (Shel Belle) and my birthday. All of our kids were there, gathered around the table, and our hearts felt so full. We wanted the whole gang there. Wouldn’t have had it any other way.
Our families did everything together. We even lived on the same road. All of our kids grew up together, side by side, sharing everyday life — the ordinary moments and the big ones. We weren’t just friends; we were family.
The babies — Ty and Lou (Bernadette) — were sleeping peacefully in their carriers beside us while we talked, laughed, and lingered longer than planned.
And then, right in the middle of dinner, Randy said it:
“We should go caroling this year”
It wasn’t a big announcement. Just one of those simple ideas that somehow lands heavy with meaning.
That night didn’t end at the restaurant.
After dinner, all of our families went on carriage rides together — cold air, bundled kids, laughter, and that feeling you only recognize later, when you realize you were standing inside one of the best nights of your life.
It truly was the best night.
And none of us knew it would be the only Christmas season Randy would be there to go caroling with us.
From an Idea to a Tradition
Randy wanted a way to truly share the holiday — not just with decorations or gifts, but with love, presence, and community. He believed Christmas was meant to be experienced together, and he wanted people to feel remembered and cared for during the season.
So the next thing you know, we had it all planned out.
Horse trailer and all.
We made it happen the very next month — December 2005.
Built by the Guys, Filled with Love
Before we ever sang a single note, the heart of it all came together through teamwork.
The Diss, Dittmer, and Graham guys were the ones who decorated the Diss's horse trailer and made it warm and cozy. Rubber mats lined the floor. Straw bales were hauled in for warmth. Lights were added, details were handled, and everything was made safe for a trailer full of kids and adults.
And yes — once or twice, we even used a heater back there.
Homemade hot chocolate was always on board.
That trailer wasn’t just decorated — it was built with intention, friendship, and love.
A Horse Trailer Full of Joy
Once it was ready, everyone piled in!
Bundled-up kids with red cheeks and bright eyes.
Laughter echoing off walls.
Christmas songs spilling out before we ever arrived. Feeling every bump in the road and every snow drift we plowed through.You could hear us coming long before you saw us.
Songs We Held in Our Hands
Ruben and Tara's niece, Rachel, created a caroling songbook just for us. Enough for everyone— pages filled with familiar Christmas hymns and songs we all knew by heart, including Grandma Got Run Over By A Reindeer!
Those songbooks mattered more than we realized at the time.
They kept everyone singing together.
And they made the whole night feel intentional — like something we were building, not just doing.
I can still picture them — all clutching them tightly as our voices filled the freezing night air.
The First Year
That very first year, it was just a small group —
the Diss’s, the Dittmer’s, and us Graham's.
We went to just under ten houses, standing on front porches, in drifted driveways and singing to people we knew. Some were known to all of us, some just to one family — but every stop mattered.
We weren’t trying to perform.
We just wanted to bring a little joy.
To let people know they were loved.
And you could see it on their faces — surprise, gratitude, sometimes tears. Doors opened wider. Smiles lingered longer. For a moment, the world felt softer. Some would ask if they were on the list for next year or could we go to so and so's next year because they would love it.
What Came Next
That first December — December 2005 — was the only year Randy went caroling with us.
He passed away the following May of 2006.
God carried all of our families through the tragedy of losing Randy.
What Randy started that first year didn’t end when he was gone. Year after year, we kept going — not because it was easy, but because it mattered.
When the After Party Took On a Life of Its Own
As the years went on, the caroling didn’t stay small.
More families joined.
More kids and friends climbed into the trailer.
More voices joined the songs.
And eventually… the after party got so big that we had to move it to the township hall 😂.
There was music playing and lots of dancing — kids spinning around, adults laughing, boots tapping the floor. Long tables filled with food. Coats piled high. The room buzzed with joy. You may even find some tired babies asleep on a saddle or on a feedbag in the end.
What started as a few families singing at front doors had turned into a full-blown community gathering — and somehow, it still felt just as personal.
Those nights were loud, messy, and full of life.
Exactly the kind of joy Randy had hoped for when the idea first started.
The People Who Made It Happen
None of it would have existed without the people who showed up — year after year.
The ones who decorated the trailer, drove and sang.
The ones who loved our kids like their own.
Tom, Shelly, Cody, Carly & Cally Diss
Ruben, Tara, Teresa, Richard & Bernadette (our sweet Goddaughter) Dittmer (Ruby & John Paul arrived in the later years)
Randy, me, Lane, Clay & Ty Graham
Friends that are family. Such a gift. Such a season.
And who knows… maybe someday you’ll see that caroling horse trailer rolling through the Grand Ridge countryside again on a Christmas Eve Eve evening — voices singing, Homemade hot chocolate steaming, hearts full.
PS In the picture we are missing a few of our kids...Cody Diss, Cally Diss & Clay Graham. We have determined they were in the truck staying warm. Bernadette Dittmer & Ty Graham were with Ms Tara's Mom and my Mom because it was an extremely cold Midwest night🤍🎄⭐️