I did this, many years ago. We had a very fancy TB mare who was just awful about loading. The final straw was three hours at a horse show to get her on. I brought her home, and fed her in the horse trailer for a couple of weeks, and that was the end of it. Make sure that your trailer is either still hooked to the truck (which is a pain to leave the truck out, and it can get damaged) OR that you block the trailer extremely well, if you are going to try and let them go in and out in a paddock.
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If you have a small-ish paddock. Back the trailer up to the paddock gate, put breakfast/dinner in the open trailer, supply plenty of water out of the trailer, turn horse loose, and go about your business. He’ll get curious/bored/hungry. We’ve left one overnight and just let him go in and out at will. Then we started to have him follow someone in for a meal. Then for a treat. Then we started shutting the doors for a few minutes. The we took him to the end of the driveway. Then around the block. Then for ice cream.
