1. Preheat oven to 400 °F. Halve the acorn squash lengthwise and scrape out the seeds. Brush the flesh with 1 tablespoon melted butter, then sprinkle with 1 tablespoon dark brown sugar.
2. In a medium bowl, mix the cranberries, apple or pear, oats, cinnamon, 2 teaspoons dark brown sugar, and the toasted almonds. Spoon mixture into squash halves, dividing equally, and dot with 2 tablespoons butter.
3. Bake for 55 minutes, then cover with foil and bake until squash is tender, 15-20 minutes longer. Let cool slightly before serving.