According to Michael Winters, the actor who plays Taylor Doose on Gilmore Girls, we have confirmation of the return of Dakin Matthews, who played Headmaster Charleston. This news comes from an interview between Michael and the Gilmore Guys.
We knew from earlier spoilers that Chilton would be featured on the show in some way, so now we have to figure out how. We don’t think any of the kids are of age to be at Chilton, so maybe it’s a reunion? Or a retirement celebration for the Headmaster?