Its not necessary to have a chilled happy hacker type horse to enjoy trail riding, but it is important to have a horse that you can trust.
Working outside the box (literally) is a great way to teach your horse to listen to you in a different environment -which makes it even more important if you plan on competing or attending events with your horse.

Expect the unexpected outside. You may ride the same route every day for a month and not have any problems, only to find the next day after a heavy storm, that the trail has washed out where you normally let your horse canter.. or that a farmers’s rouge bull has escaped into a field you always ride through.
Be prepared for the worst without expecting the worst is the best key for a fun and most importantly SAFE ride.
1: Wear a helmet that fits well. Dont make that all to common mistake of not buckling it up. You may as well not be wearing it in this case. In the world of western riding wearing a helmet is still not as common as in the english riding scene. I myself can admit to riding for years without a hard hat, Il admit to changing my mind only when I heard about a former employer of mine (a top dressage rider) who lay in a coma for three weeks after her safe, steady 15 year old horse spooked on a trail ride.
Even the best horse can fall, spook etc so why risk your life, and the lives of those that would have to look after you if you injured yourself?
2. Before you even get on, check your prepared for the ride.
– Is your gear well oiled and cared for. Make sure you check girths, bridles, and stirrup/fenders for any cracks. Tack breaking at the wrong moment can be deadly – so spend that extra five minutes looking over everything.
Is your cell phone charged? If things go wrong, do people know where you are heading? Have an emergency contacts number written in your saddle bag just in case….
In your saddle bags have you got water, a hoof pick,bug spray, sunscreen, lip balm, maps, an easy boot (in case you loose a shoe) and leather shoelace baling twine for emergency fix-it jobs. I always take a snack too, as if the ride takes longer than expected it can help keep my blood sugar from getting too low.
3. Check over your horse before you leave. Even horses turned out 24/7 should be lunged first and warmed up before a ride. Check his shoes are looking ok. Make sure hes clean under his tack to avoid rubs,and put on leg protection.
Before you leave your horse should stop well, turn well and be controllable in all paces. Equally important is that you gauge your horses level of fitness for the ride.
If hes been boxed up all winter.. dont expect him to do an eight hour ride straight away. Start slowly, and work your way up. Its not worth risking an injury because you didnt sort out a decent fitness routine earlier.
4: Keep your distance.Out on the ride be observant.
One of my pet hates on trail rides is when riders come too close to a horse they don’t know. The rule of thumb is to keep all horses two horses apart at all times on a ride. If you don’t know the horse you are riding, it is nothing more than suicidal to bring him or her close to another horse.
I have seen kicks to riders in this instance, and they are not pretty. Horse are not cars, and they have bad days just like us. Even best pal paddock mates can strike out at each other when in season/in a bad mood etc.
5: Dont stick in the same spot on a group ride. Move your horses position now and then… put him in the middle, at the back, up the front.
He wont expect to be at the front the whole time if you do this, and when he is at the front he will learn to be more assertive if hes not normally so. Keep your horse thinking, and he will learn from the ride as well as enjoy it.
6. Challenge your horse on the ride. If he spooks at things, stay calm and ride on. If you need to cross water – let him think, drink, touch the water. Be determined. Your horse wants a leader, if you are not confident enough to get him through small things like a stream.. what will happen when you face a river? Don’t overuse your reins either.. they are not the only aid. Use your legs and your seat get your horse to move where you want him to go.
He wont think less of you if you boss him about a bit -he will feel more secure.
Remember the cardinal rule to keep your horse moving forward in times of stress. If he sees a herd of cows, rather than stopping him and allowing him the chance to play up and fret..its better to keep him moving to allow him to move away. If you want to get him used to the cows, ride him around them. Dont force him to stay still, thats messing with his prey animal instinct to run. If you keep him moving around them, he will soon figure out they are not anything to worry about.
NB. be careful of tie-downs or side reins on rides out as they will restrict the horse in water crossings, and even cause him to flip over if he rears.

7. Dont push your horse. If hes 18 and of heavy horse breeding, hes not going to keep up with the 6 year old Arabian at the front of the ride.
Trail rides should be relaxing, and about mutual enjoyment. If you want to spend the whole ride at a gallop, maybe you should consider buying a motorbike.
If you must return using the same trail, take attention not to rush home. Take it easy, and you will avoid a very dangerous vice -bolting for home.
8. Cool your horse down. Walk the last mile back, even better -walk him in hand for 5 minutes at the end of the ride with the girth loosened slightly to prevent lactic acid building up.
9. Check him under his saddle,wash him down, and check his shoes. Dont feed him grain straight away as you will risk a colic.
Most horses simply need experience to make them great trail companions. Even the spookiest horse will calm down if he goes out daily under the guidance of a calm, respected, leader.
Keep yourself and your horse safe by following the tips above, and with the experience gained on the trail; your horse will become more confident, self assured and responsive.