One of the most important things to do when you are starting to plan your roots travel is to pick up a history book.
If you really want to connect with your ancestors, you will want to be able to understand the world they lived in. You can do that through history books, newspapers of the day, etc. However you read your history, it is vital that you understand both local and world history.
Try to look for anything that might have affected your ancestors. Was there a flood that year in the neighborhood? Who was president and what policies were in place that might have affected your ancestors? What businesses advertised in the newspaper? Is it possible your ancestor frequented them? What was going on in the world?
By understanding the world your ancestors lived in, you will better understand your ancestors. You might find places that are still around that were around when your ancestor lived. You will find differences and similarities to our time. Those differences and similarities will become the framework for your travel, as you try to understand the world your ancestor lived, grew up, and died in.