Preheat the oven to 375°F and line a pan with parchment paper. While the oven is preheating, tear the two slices of bread into small pieces, removing the crust, and soak the pieces in the milk for 5 minutes.
2 slices Bread, ½ cup Milk
Mince the garlic and parsley, and squeeze the excess milk from the soaked bread crumbs.
2 cloves Garlic, ¼ cup Parsley
Cut the squash in half, then use a round spoon to scoop the seeds out of the center. Discard (or save for baking and snacking on later!).
2 medium squash
If you're using round squash, slice a thin sliver off the bottom of each squash half so they sit flat on the pan, then move them to the pan.
In a large mixing bowl, combine the sausage, garlic, parsley, bread crumbs, red pepper flakes and egg, mixing well with hands.
4 links Italian sausage, 1 Egg, 2 teaspoons Crushed red pepper, Salt
Stuff the squash halves with the raw sausage mixture.
Top with shredded cheese and a sprinkle of olive oil.
½ cup Cheddar cheese, Olive oil
Cover in aluminum foil, then roast for 30 minutes. Remove the foil and roast another 30 minutes, until the squash is tender and the cheese is golden brown, then serve!