The first part of taking your Jeep offroad is to figure out where you are going. You may already have an idea of the trails in your area and know where you want to go. Or you may want to explore some new areas. Good places to find Jeep trails include sites like this one, other Jeep forums, and local Jeep clubs. Jeep clubs often have organized runs to help you get familiar with trails in your area. They also typically have experienced trail leaders who can show you good offroading techniques.
Once you have determined where you are going, you should learn everything you can about the trail and area to which you are planning to go. Read descriptions about the trail. Use mapping software such as Google Earth get an idea of how the trail area is going to look. Download gps tracks of the trail to use while you are on the trail.
Check the weather. Have an idea of what the weather will be on the day of your run. Depending on the trail you are running, having good weather conditions can make the difference between a fun day on the trail, and a disasterous day. I am not suggsting that bad weather by itself will make a bad day wheeling, however it can greatly the changes of getting stuck or making a relatively easy obstacle more difficult. Prepare for weather accordingly.
Now that you have figured out where you are going, it's time to make sure that your Jeep is ready for the trail. It is important that each of these steps is taken before each trail run. An ounce of prevention is worth a pound of cure, and that is certainly the case with your Jeep.
By checking and correcting the items listed above, you will avoid 90% of the mechanical problems you may encounter on the trail
This is not a comprehensive list of all things that you should be carrying with you on the trail, but does cover the basics.
By having these essential thing with you on the trail, you should be able to handle most problems you encounter. Obviously if you become severely broken down with a broken axle or other catastrophic failure, you will need to be helped off the trail and towed home. It would be impossible to carry with you an entire auto parts store, but these basic supplies should cover a majority of your trail issues.
Having a good understanding of trail etiquette will go a long way to make the Jeeping experience for you and the others around you great. Many different people runs trails in different ways. Some clubs have certain rules that you need to follow if you want go on their runs. So check with the group with which you are travelling to see if they have specifics that you need to be aware of. But in most cases following these guidelines will be expected.
Much of this is common sense. But you would be surprised by how many times you will encounter someone who just doesn't get it and will make the run annoying for everyone.
When you are done with trail, air up your tires, connect your sway bar, and do a visual inspection around and underneath your Jeep. Check for loose or broken parts. Check your fluids again. Thank the trail leader and exchange any information with the new friends you have made on the run. When you first get back on pavement, start driving slowly and see if you feel like there is anything out of the ordinary. Stop and check if anything isn't right. Once you have confirmed the Jeep is driving as it should, you can slowly go up to freeway speeds and head home.