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1. Preheat oven to 350 degrees F. Brush a 1 1/2-quart baking dish with softened butter. Prepare Bourbon Caramel Sauce; set aside to cool slightly.
2. In a 4-cup liquid measuring cup combine the half-and-half, eggs, and vanilla; whisk to combine. Whisk in 3/4 cup of the Bourbon Caramel Sauce. Set aside. In a large bowl toss squash with brown sugar and cinnamon. Add the whole wheat bread, pear, and cranberries; toss to combine. Place in prepared dish. Slowly and evenly pour egg mixture over top. Let stand for 5 minutes.
3. Bake bread pudding 1 hour. Remove from the oven let cool 10 minutes. Top with fresh pear, mint and cranberries. Reheat remaining sauce. Drizzle some sauce over bread pudding and pass remaining.
1. In a heavy medium saucepan combine brown sugar, whipping cream, butter, and corn syrup. Bring to boiling over medium-high heat, whisking occasionally. Reduce heat to medium. Boil gently for 3 minutes. Remove from heat. Stir in bourbon, vanilla and salt.