To prepare the horse for a 2 hour trail ride, a day long ride, or a weekend ride, condition the horse with shorter rides. Begin your fall riding with an 1-2 hour ride at a walk. As the horse, and you, get back in shape, gradually increase the distance of your rides before increasing the speed of your rides. Make sure the hooves are trimmed, and if your horse is tender footed walking on stones, you may need to consider shoes or boots.
Oil the breast collar well, and check to make sure it lies close but not too tight across the front of your horse. The breast collar will keep the saddle from sliding back. Some trail riders use a crupper as well, which attaches to the back of the saddle and goes around the underside of the tail, to keep the saddle from sliding forward.
Saddle bags come in all types and sizes. Take special care in attaching them to your saddle so they are no loose and bouncing on the horse, causing your horse to have sore backs and shoulders. It is wise to carry a knife, vet wrap, extra latigos or string, a small first aid kit, and water. Think about carrying your cell phone on your body, so that if you get separated from your horse, you can try to call for help.
Begin at home to get your horse prepared for trail riding. Put 3 logs on the ground, 3’ apart to walk and trot over. Practice side passing both directions in case you need to move away from a hole on the trail. Practice side passing to and away from a gate, and then try opening and closing a gate. There are very few, or no, gates at most of the lake trails. Get your horse used to being tied to the trailer, and saddle and unsaddle while being held, and then tied, at the trailer. Practice loading and unloading before the day of the ride.
Riding with a friend or two is a great way for both you and your horse to get accustomed to trail riding. Enjoy the outdoors and have fun riding your horse this fall.