Trailer loading is one of those skills that every horse owner eventually needs and that surprisingly few horses have been systematically taught before the first time they actually need to go somewhere. Teaching a young horse to load correctly and willingly from the beginning, in a calm and systematic way with no deadline pressure, is one of the most valuable investments you can make in the horse's long-term manageability. Begin the preparation before the trailer is involved by making sure the young horse leads correctly, stops and stands on a light cue, and generally understands the concept of going where he is directed even when uncertain. A horse that does not lead well on the ground will not load well into a trailer, because loading requires the horse to trust the handler's direction enough to walk into a confined space his instincts tell him is potentially dangerous. Introduce the trailer as an object to investigate before asking the horse to enter it. Park the trailer in a familiar location and allow the young horse to approach it, sniff it, walk around it, and examine it at his own pace. Open the escape door, open the back doors completely, and allow as much light and airflow as possible to make the interior as inviting as possible during initial training sessions. Build the approach incrementally — today he walks within ten feet without tension, tomorrow within five, the next day he touches the ramp with his front feet. Front feet on the ramp is a major milestone and deserves significant reward and a session-ending release the first time it happens correctly. Do not immediately ask for more — let the horse stand with his front feet on the ramp, feel the surface, look into the trailer, and process the experience without additional pressure. Once all four feet are in the trailer, do not immediately close the door. Allow the horse to eat hay from a net if you have prepared one inside. Begin closing the door only after the horse is consistently loading and standing quietly with the door open through multiple sessions. Feeding the horse in the trailer as a regular management practice builds a strong positive association between the trailer and something the horse genuinely wants — a horse that walks in voluntarily for his grain is the destination of all trailer loading training.
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Watch: Tips for Trailer Loading a Young Horse

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Clinton Anderson: Trailer Loading Made Easy — Tips for Trailer Loading a Young Horse
Downunder Horsemanship