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