So, you want to trail ride? Don Jessop

Don JessopBreakthroughGuy
4 min readMay 13, 2024

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So, you want to trail ride? Don Jessop

I can say, with total confidence, after thirty years of riding horses, and twenty of those years as a professional, that most people still do trail rides wrong. ​”Wrong” isn’t the right word. I should say… There are better ways.

​There are a few things that once you are aware of, make every trail ride better, safer, more fun for everyone, and leave the horse with a good taste in their mouth about you as their leader. In no particular order, here are some of those things that get missed:

​1. Get off and walk the last hundred meters with a loosened cinch. Riding up to the last second can cause your horse to hurry home. Walking the last leg will cause them to keep and even temperament and calm expression about finishing the ride. Remember this motto. “Horses tend to remember the last thing that happens.” Getting off and walking back leaves a great, bonding, feeling about your partnership and prevents barn sour horses from developing.

2. When in a group, the most novice rider and horse should dictate the speed of the ride. As a group leader, I always check on my group’s skill levels. And every time, without fail, I encourage the group to meet the needs of the most novice rider or horse. If we don’t, we risk injury, and we’ll likely never see that rider on the trail again. Group rides are a community experience. AS individuals grow their confidence, you can all set out like you’re John Wayne and Calamity Jane, but in the beginning, take care of each other. Don’t leave a novice rider to their own devices because you feel like cantering off into the sunset. Do that on your own, when you’re certain you’re not going to put someone in a sticky situation fighting for their horse’s attention.

3. When approaching something scary, triple down on your patience level. Get off and lead if you have to. Still today, I meet trainers, who are adamant their horse will learn something bad if they get off. It’s not true. IN fact, it’s quite the opposite. Read my “Come to Jesus” blog post to learn more.

4. When something scary is approaching you, face the problem. It’s even smart to get off sometimes and set boundaries from the ground. Safety is important. If you know your horse and have already been through the worst of his funky moments, you might be confident to ride it out. But if you’re uncertain, just get off and get through it. Wail till they’re okay with everything and then get back on and win in the end. Read my “Come to Jesus” blog for more.

5. Take a break from time to time. Especially, away from home. You’re not just there for your own benefit. You’re there for your horse too. You want your horse to have a good time and learn to enjoy heading out with you. I want my horse to feel rewarded for going out, so I plan grazing areas and resting places away from home. It’s a nice way of saying, life is safe and pleasant out there instead of in our limited little home environment. This tip alone, makes for a great trail horse.

6. Don’t just follow the trail. Beat your own path sometimes. If you’re following a horse and rider in front, don’t step where they always step. Make micro-leadership impressions by going around the rock to the right instead of following the horse in front that went to the left. It’s amazing how this builds attention and confidence for both horse and rider and keeps you engaged and responsive to each other.

7. When you arrive at the trail to start your journey, hurry up and chill out. Don’t be rushed to get on and go. Eat a sandwich, slowly sip your coffee down. I’ll never forget my early instructor saying how smoking a cigarette is bad for your health but great for your horsemanship. Your energy can overwhelm your horse and leave a bad taste about you and the trail riding experience.

8. In groups, swap leadership positions often. It’s good for everyone, especially the novice riders. Even just a minute or two in front, once or twice per ride, will enhance the skills and confidence of the most novice horse and riders. Don’t be in a hurry to be the leader or the follower. Find time to be both. Be there for the community experience.

Can you think of some things I’ve left out? I’d love to hear from you, dear reader. You’re my inspiration to keep writing and sharing.

See you all again soon. Don Jessop

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Don JessopBreakthroughGuy

Don Jessop created Mastery Horsemanship for you! www.masteryhorsemanship.com provides you with safe, fun, and useful next steps in your own journey with horses.