100ft long by 75ft wide arena?

It buries when it turns hard. Even my tractor gets pissed when I turn too sharp, and I have to hike the drag a little to get going again.

With regards to getting a tractor, for many jobs on a small farm a modest, older tractor can frequently be found for around $2000 or under, will work and be relatively easy to work on if something breaks. I have a 1940 Allis Chalmers B that pulls the manure spreader, a flatbed trailer and a disc. Models from the 50’s will likely have a 3-point hitch and can handle a mower as well. Other options would be a small Farmall or Ford 8N or 9N.

These aren’t big tractors, they won’t be able to pick up round bales or do very big jobs, but they are a very handy size and can be very useful.

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as long as the horse knows whoa it should not be an issue,

We work our horses in harness, most all that is. Lexie was expected to work but decided that thing she was dragging was trying to eat her… caught her as she rounded the round pen on the second trip around the outside… no harm to her but she has not been in harness since

My indoor is 80x140 and that’s as small as I’d want to go. It’s completely adequate- I can squeeze in a full course when I need to. But it’s mostly for flatwork an is sufficient.

Could you buy an ATV with a chain harrow to pull behind?