Something that "is headed toward" a place is moving in that direction. People usually use "headed toward ___" to talk about things in the air, like storms and airplanes, or about people who are walking:

Oh, I see Ben over there. He's headed toward us.

You wouldn't usually use "headed toward" to talk about someone moving in a car or train. The word "toward" fits best when something is able to move in any direction, unlike a car or train that has to run on a road or track. For cars and trains, you say that they are "headed to" somewhere:

Excuse me, where's this bus headed to?

People also use "headed toward" to talk about trends. You imagine what the result of a trend will be, and then say that the society, the country, or some group "is headed toward" that result:

I think the U.S. is finally headed toward an economic recovery.

They're headed toward bankruptcy if the C.E.O. can't find a way to make them profitable soon.