Preheat oven to 400 degrees.
Combine 2 1/2 c. cooked butternut squash, 1 c. melted butter, and 1/4 c. skim milk in a bowl and blend with a hand blender until smooth (like 1-2 minutes or so).
Add 1 tsp. cinnamon, 1/4 c. packed brown sugar, and can of apple pie filling to the squash mixture. Blend again with a hand blender until mostly smooth, some apple chunks remaining is fine.
Add 2 c. crushed graham crackers to the mixture and stir by hand until moistened and fully mixed.
Spray a 9x13 inch glass baking dish with cooking spray. Spread the batter in the prepared pan and flatten batter using the back of a large spoon.
Bake at 400 degress for about 55 minutes.
Prepare the topping for the bars after putting the bars in the oven by combining 1/4 c. pieces of dried apple, 1/4 c. dried cranberries, 1/4 c. crushed nuts,1 Tbsp. packed brown sugar, 1/4 tsp. cinnamon, 3/4 c. oats, and 6 Tbsp. melted butter. Stir and let mixture sit to soak up butter while bars are baking.
Remove bars from the the oven after 55 (to 60) minutes. Spread prepared topping mixture over bars. Bake for 15 minutes. Be sure to remove the pan from the oven before the dried fruit topping starts to burn.