Can you enter silent hill

I'm afraid not

Technically no, as far as I'm aware there is no actual 'Silent Hill'. However, There is the town that Silent Hill (the movie) was based upon called Centrailia, PA.

But Just like Silent Hill, there is an underground coal fire that's been burning for the last 40 years. You can not actually enter the town due to high levels of toxic gas and sinkholes. You can however visit the outskirts and surrounding towns! I actually live about an hour away and its pretty eerie place!