I was at WDW this past Christmas. We did the sleigh ride at the Wilderness Lodge. I called 1 week before we left (because I couldn't decide if I really wanted to do it) and there was 1 reservation on Christmas Eve that someone had cancelled. We were very lucky! So be sure and call early to get the date and time that you want.
It was a nice ride. The wheels were covered so it looked more like a sleigh. They had big blankets to cover up with, which was nice because it was chilly at night. You go through the parking lot and then on a walking/running trail. Then you turn around and go back. It lasted about 30 minutes. It was dark so you couldn't see a whole lot. It would be really cool if they would put up some Christmas lights out there in the woods!
Port Orleans Riverside also has carriage rides. We passed one that night. It was a covered carriage. Not sure if it runs year round, but there is probably someone here that knows!
Hope this helps you!
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