Preheat oven to 400° F and line two baking sheets with parchment paper.
Spread the bread cubes out in an even layer on one of the parchment-lined baking sheets. Bake for 10 minutes. Set aside until ready to use.
While the bread is in the oven, prepare the acorn squash. Using a sharp chef's knife, carefully trim a little off the top (including the stem) and bottom of each squash, just enough so that it will stand upright on either side, but not enough to make a hole.
Carefully cut each squash in half horizontally.
Scoop out the seeds of each squash half with a spoon or ice cream scoop.
Place the squash flesh side up on the parchment-lined baking dish.
Brush ½ teaspoon olive oil onto each squash and sprinkle with salt and pepper to taste. Flip the squash over so that it is flesh side down.
Once the tray of bread cubes has been removed from the oven, roast the squash until it is easily pierced through by a fork (approximately 30 minutes).
After the squash has been roasting for 20 minutes, make the stuffing. Heat olive oil in a non-stick pan over medium heat.
Add the chopped onion and season with salt to taste. Cook on medium until the onion is translucent, about 3 minutes, stirring frequently.
Add the chopped pear and cook on medium for another 2 minutes.
Turn off the heat and add the bread cubes and the remaining stuffing ingredients. Stir until the bread absorbs the broth. Set aside until ready to use.
Carefully flip over each of the squash halves. Tongs work well for this since the squash will be hot. Fill each squash half with the stuffing mixture. Lower the oven temperature to 350° F and bake until stuffing is lightly browned and heated throughout (approximately 10-15 minutes).