There are two "tricks" I have found to make history much simpler to learn. The first is to realize that time is always in motion and to track the cause/effect relationships throughout time (see "Time is a Flow"). The second is to apply emotions to history, and by that I mean to put yourself in the shoes of those before you.
For example, I am tutoring two students in American history, currently at the events leading up to and including the Declaration of Independence. So, put yourself in the colonists' shoes. WHY were the set of acts setup by Britain so awful? WHY did the colonists have no choice but to rebel? Well, if you pretend that you are a colonist, the answers start making sense:
You are being ruled by a monarchy across an entire ocean. At this point, you were probably born in America, so you have never even been to Britain. Yet, this king decides all of the laws for you and places taxes on items you use everyday... for what? To send more troops over to steal your jobs and live in your homes? Why do you need to pay money to some obscure power that is trying to control your life, or at least your money?
Once you have a grip of how a colonist might have felt, turn the tables and look at it from the British point of view:
You originally financed (either directly or indirectly) the expeditions that colonized America. You just finished fighting a costly war with the French (and Native Americans). You are heavily invested in America because of mercantilism. They originally were good sources of income but have recently been trading with other countries, lowering your profits. The colonies are really more of a business to you than anything else... a business where the employees are rebelling. If you are soft to them, other colonies you have made (especially India) may join in rebellion. You have to regain control no matter what to send a message, not only to them, but to all the world that you are not to be messed with.
Once one can at least partially understand the reasoning behind each piece of history, the parts start coming together and making more sense. And, when history (or any subject) makes sense, remembering what happened for tests and essays becomes much simpler.
(If you have enjoyed this blog, please leave a comment to let me know. I love to blog to help others, but it helps me to know that people are indeed reading them. I do respond to comments, so feel free to check back after a day or two and see my reaction if you desire. If you have ideas you would like to see in future blog posts, please let me know. Also, a thank you to Justin in the feedback forum for looking into improving the blog structures.)