1. To move or guide someone or something into some place or thing. In this usage, a noun or pronoun is used between "head" and "into." If you head the car into that space carefully, I don't think you'll hit the cars parked on either side. Head the kids into the classroom and get them set up for naptime.

2. To start moving the front end or part of something into some thing or place. If you head into that space carefully, I don't think you'll hit the cars on either side of you.