"Bend" in horse riding can be explained fairly easily: the horse bends his body into the arc of the circle that he is travelling in. Think of the curve of a banana as an image in your mind.
Although it's not possible for the horse to actually bend his spine (the way you see in drawings showing a horse along an arc of a circle), the horse can bring both his hind end and his front end "in" (toward the inside of the circle). This allows him to maintain better balance as he negotiates the curve of the circle.
Sounds pretty simple, right? Then you get to work on it and discover the seemingly endless things that can go wrong.
Bend is something you can start fairly early in your riding career (or your horse's training career) but you'll notice that it's one of those things in horse riding that never really becomes perfect. Just when you think you've got it, you'll discover something new that will make it easier, softer, bouncier, looser... and you will just keep dipping deeper into that proverbial well that is "bend".
Not a bend.
Let's start with what isn't a bend.
The Neck Bend
We often think that pulling on the inside rein will get the horse bending. So we pull away, and the horse bends... his neck.
This causes the horse to send his neck into the direction of the turn, but his body doesn't necessarily follow. Instead, he now has to negotiate balance without the use of his neck (which is essential for balance). His inside hind leg is also blocked by the pressure on the inside rein, which then forces him to disengage in the hind end. This causes further balance problems.
Sometimes we can keep the front end on the arc of the circle, but leave the hind end to itself. In this scenario, the horse travels along the circle with the haunches trailing off the arc. While the front end looks like the horse might be on a bend, the awkward hind end means only one thing: not bend!
Other times, rather than pulling the neck around, we ask only for the horse's head to turn in. We leave the neck straight(ish) but instead, ask for the horse to look in the direction of the turn. So while the horse's head is directed into the turn, his body may be straight or even mildly counterbent as he moves along the circle.
While flexion is a component of bend, it is not enough.
What a bend really means.
A true bend is a combination of the head, the front end of the horse and the hind end. It's a whole-body position that requires suppleness throughout the body.
First, ask for flexion. The horse looks in the direction of travel.
Second, bring the front end to the turn. Use your inside leg to push the horse to the outside rein. Your leg is responsible for the control of the inside shoulder. Even though the inside shoulder is coming toward the arc of the circle, make sure that the horse isn't just "falling in" - cutting the turn so that you end up coming off the circle onto a sort-of diagonal line.
The outside rein (often called a neck rein) maintains the arc of the front end. Not too much arc but not too little - just enough for the circle you're on. It also acts as the turn aid when you want to move into a turn.
Third, bring the hind end to the turn. The haunches can come in "just enough" to maintain the arc through the body. This job goes to your outside leg, which encourages the horse to bring the hind end off the straight line and into the turn. It also prompts the horse step underneath better with his inside hind leg, which will help him have better balance through the turn.
This is the overall picture.
Let's say you are travelling down the rail to the right and you have a 20-metre circle coming up at E. You move along the straight line (probably in a small shoulder-fore as you set up for the turn). Then as you pass E, you start heading into the circle.
Get the flexion even before you leave the rail - so the horse is looking into the direction of travel. Front end comes into the turn and the hind end follows, with the haunches also on the arc of the circle.
At first, you might have trouble coordinating all the aids - inside leg, outside rein, outside leg. You might get one aspect of the bend but not the other two. Your horse might be stiff in the front end, the hind end or both.
Then you might get a bend but it feels like you're working really hard. Maybe there isn't enough impulsion, or the horse "leaks" in the shoulders or hips.
Eventually, though, it gets easier - for both you and your horse. You become looser, more supple. Your aids can be softer. Your horse can distribute his weight easier on the turn.
Then you develop that suppleness into all the gaits. Each gait has a different feel.
Then you learn there is even more - something called the (intentional) "counterbend" (or "renvers" in dressage). But that is a story for another day!
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Read more here:
What Is Neck Bend? And What To Do About It: A detailed analysis of neck bend.
Bend: How To Drift Out On Purpose: An excellent way to begin to learn what bend feels like.
18 Reasons To Establish "Forward" Energy: Hint: it helps with bending!
Get Rid Of That Tension: 4 Steps To Improved Suppleness: On the one hand, “finding” suppleness can be a rather long term and difficult undertaking, especially for novice horses or riders. On the other, suppleness is the key to all good movement.
11 Unexpected Side-Benefits Of Riding Tests (Or Patterns): There is something to be said about putting yourself through tests or patterns. If you rarely ride a pattern, you might initially be surprised how difficult it can be to ride according to specifications. But it is very much worth the effort.