in the past w/ my apples, i've made the pie filling, put plastic wrap in the pie pan, then the filling, close it over and freeze it... maybe make 6-7 fillings... then when frozen, take them out of the pie pan, still wrapped in plastic and then into a zip lock and stack them in the freezer.
it can be fun trying to match the filling size with the pie pan used to freeze them, but it's sure easier later when baking to have the filling done. and... those pears do look wonderful! I've never tried the red hots but have heard about them and will try them also...