I mean, we keep getting told how much fun it is. But sadly, the opportunity has never come my way.
You?
Yep, I’ve ridden in the sleigh that my stepfather made for the farm. Used to haul one thing to the other side, pulled by the current strongest horse. He called it a sledge. We especially used it in the snow which made it easier to glide, although it was also used across just plain grass.
No jingle bells or fur trimmed robes, but it was still neat to ride through the snapping cold with a load of hay to go feed the cattle. Didn’t need it to go over the hill to see Grandma; she always came to our house.
Back when I was five y.o., I got a chance to go for a ride on a one-horse open sleigh on a crisp, white winter morning, along with a bunch of other kindergarteners. I was seated right behind the horse’s behind, and vividly remember the staunch stench of shit emenating from the beast’s anus.
My SO’s grandfather was an amazing man who handmade a sleigh for his pony. We took it on the ice. So pretty much all the conditions of the song, though it was a pony, not a horse and we were dashing over ice with just a little snow.
Opa H. died early this year. We were over at Oma H.'s for supper yesterday. It was the first time we were there that we heard her say grace, instead of Opa. I showed her the pictures of the coffee table I made, and said how much I wished he had been around for advice. She said the coffee table looked good, and that he would be proud of me. That made me happy. Somehow I really bonded with my Grandfather-in-law. He was a quiet man, but we always chatted loads, often about horses and other animals.
I miss him. I’m pretty lucky to have had a Grandfather-in-law who was like a grandfather to me 
One of my uncles had a sleigh and they’d pull it around with a snowmobile. It was mildly interesting as a novelty.
I learned how to break (train) a horse to pull a cart, so I have been in and driven a one-horse open cart, but never a sleigh.
I remember a few years ago when I lived in a very rural area, taking the dogs out for a walk on a very crisp, January night after a snowfall, where the moon was so full and so bright that it was throwing shadows and thinking that this would be the perfect night for a midnight sleigh ride. Alas, no horses or sleigh.
Choosing the middle option due to having ridden in the neighbor’s wagon pulled by two percheron draft horses. There hasn’t been enough snow remaining on the ground to have the horses pull the sleigh. So far, the rain washed away what snow fell last week, so this year might be a wagon again. It’s fun!
“open sleigh”? I thought it was a one whore soapin sleigh! I pictured hookers and suds and bubbles and …
Well now that makes the song different.
I’ve ridden in a wagon pulled by a pair of horses (and sung the song with gusto, altering lyrics as appropriate), and maybe ridden behind another set of horses in snow–I can’r remember the vehicle well enough to be sure that “sleigh” applied.
I have ridden in a two-horse open sleigh. I thought it was pretty darned awesome.
Yup. In Salzburg, during the time between Christmas and New Year, with jingle bells, during a light snowfall, snuggling up to the man I would marry four months later. It was absolutely all that.
About 10 years aog, my husband’s business partner rented one for his holiday party. It was fun. Hard to do with the mild winters we’ve been getting lately.
I have seen sleighs, but I’ve never ridden in one. If I did, I’d prefer a higher end model, two horses at least, and a hard-top.
When I was a kid my great grandmother had two sleighs in her barn. They were rusty, dilapidated and way past their sell-by date by then, but I used to play on them and thought they were pretty cool. Does that count?