Meanderer, that *might* be a snow compactor. This Article mentions that similar rollers were used so sleds could run more easily.
"Back when horse-drawn transportation was the norm, snow was actually not as much of an impediment to travel as it is today. ... As long as the snow was packed down tight, it was actually better for sleigh travel, so instead of clearing away snow, your town’s local "snow warden" would hook up his horses or oxen to a snow roller."
"Put a little something together of our 46 horse hitch, driven by one man and no one leading after the first round using just two lines and the rest bucked back and tied ahead with the best hitch of them all, a talkington!
we pulled a 26' deep tillage, recommended hp was 150 and the 46 and the right hitch pulled it to a depth of 7" with ease.we farmed with it for three days and worked down 40 ac, turning corners with ease after the first day, we hooked at 10am and worked until 4pm each day".