This achievement can't be missed, as it is part of the solution of a puzzle necessary to get through the game.
*** Spoiler - click to reveal ***In the past, have Hoagie climb up the chimney in the Founding Father's room and go through the window (or go up all the stairs in the house) into the attic and get the bucket of red paint.
Go outside and back to the Chron-O-John. To the left of the outhouses there is a kumquat tree. Use the red paint on it.