Click on the images above to see a full-sized image
The clue photo (on the left above or first image) is c1900, looking S down Bank Head off Hallgate at the old Grammar School Caretaker’s and Headmaster’s houses. The pupil in red is obviously escaping (or is that one of the teachers?).
The second image from 1979 shows roughly the same area, with the houses covered in ivy and an extra upstairs window added to the gable end of the Old Grammar School.