A compilation of reflections and thoughts from years on the trail:
As an owner of a trail riding stable, I have seen many people come through my barn doors. Many are self-admittedly not riders. Others claim to have skills. And some truly impress me - in the good way. I have met some of my best friends on trail, I have seen some truly impressive riders, and I've made some good stories.
One thing I have learned is that the way people describe their skills says more about what we are in for than what they actually are able to do on a horse.
Here is what your classifications via email say to me:
"I am not a rider"
This means you ride Pepsi or Dozer. It's going to be a long and slow ride, even on the short trail.
"I'm a recreational rider who can gallop"
This means you have gone on a handful of guided rides and the horse started trotting and you thought it was really fast (good or bad).
"I'm a recreational rider and I can trot and canter"
At least you know about the multiple speeds of a horse. You probably haven't taken lessons but you have been on a horse enough times to know the difference and you probably won't fall off.
"I used to be able to post a trot, but it's been awhile"
Okay, you took lessons. You're probably really rusty and are going to get continually frustrated with your deteriorated skills and lack of riding endurance. You will be severely focused on yourself, but the horse won't care because while you pay attention to your form they can actually do their job, or better yet grab some grass.
"I barrel race"
This means that you know how to accelerate but you probably don't know how to steer or stop without torquing on a horse's mouth. You let the horse's need for self-preservation act as breaks and you're going to always be testing your (and my) limits.
"I do dressage"
This means that you are going to be under-impressed with my trail horses and they will probably be under-impressed with you too. You're going to expect a higher level of control from my horses throughout the ride that they might be able to do in an arena but isn't realistic on trail. Your constant vying for control might actually tick them off as the horse frames up and collects while continually telling you to "let go and let me do my job" (Unless it is Beau, however. He will like you). Now, if you aren't a dressage rider and think that riding dressage is the same thing as winning a blue ribbon at the county fair in an on the flat walk/trot event (class of 2 riders), well, it will be severely obvious.
"I show jump and take weekly lessons"
What this tells me is that you can steer, you can post a trot, and you might actually have good form but that you can't really control a horse. You have probably always taken lessons on a push-button mount with an instructor basically free-lunging as you ride from the center of the arena. I know I do that unconsciously in the lessons I teach and that as soon as I step out of the arena the horses stop appearing to listen to their rider (they were actually listening to me). Out on trail you'll be pulling on the horse's mouth and vying for control that you're not actually capable of. The horse will get riled up and frustrated with your over-confidence.
"I ride western pleasure"
You're used to responsiveness and smoothness that you just won't find in many trail horses. That push button horse you have been sitting on is a bit different than our rugged, indestructible trail masters. And while they listen up just fine, it's a 51/49 power relationship on trail and they know how to keep themselves (and you) safe and you're going to have to let them take the lead sometimes. And for heaven sake, please shorten up your reins. You might need to do some direct reining near that corn field.
"I played polo"
This is probably the worst thing to tell me if you're not accurate! If you say you've played polo I am going to assume that you are comfortable on a hot horse, used to jigging and dancing, and capable of maintaining fast speeds around sharp turns. My horses will seem boring but they will love you and your fantastic seat and flexible reining. If you lie to me, you will end up on the very wrong horse.
"I do three-day eventing"
Okay, a little jumping, a bit of dressage and some cross-country hacking; you've been both in the arena and out of it. You know the difference between a peaceful stroll and arena work. You also know horse's abilities and how to negotiate obstacles. Win for horse, win for me, win for you too (if you're accurate).
What you should actually tell me is more about your personality and what you are looking for from your ride. While it is important to mention whether you have only been on guided trail rides, taken lessons, or ridden independently, your personality makes a big difference in the horse I choose for you. All of my horses are safe but it's like matchmaking for the perfect marriage.
Also, by only telling me about your past I won't know what you want from a trail ride. Giving me a heads up on if you want a simple ride, a couple challenges or a rugged experience will give me a better idea.