For bread pudding:
Preheat the oven to 425°F.
Place the squash cubes on a rimmed sheet pan, toss them with olive oil and roast until they starting to soften and caramelize in spots, about 20 minutes or so. Sprinkle them with salt and remove from the pan.
Turn the oven down to 375°F.
Heat the olive oil in a large skillet over medium-high heat. Stir in the mushrooms and toss quickly to coat. Sauté until the mushrooms release their juices and start to caramelize, then add the leeks. Season with salt and pepper to taste. Continue to cook until the leeks soften, about 5 minutes more. Add the garlic and cook about 1 minute. Add the herbs. Cook about 30 seconds, then add the balsamic vinegar. Taste and add salt and freshly cracked black pepper again as desired. Set aside to cool slightly.
In a large mixing bowl, whisk together the stock and the beaten eggs. Add the bread and toss to coat. Add the squash, mushroom mixture, cheese and cherries and toss gently. Pour the mixture into a large buttered casserole dish.
Cover the dish with foil and bake for 35 to 40 minutes. Remove the foil and continue baking for another 10 to 15 minutes or until the bread pudding is nicely browned on top.
For bourbon cherries:
Combine the sugar, orange juice and orange peel in a small saucepan. Place the pan over medium-high heat and bring to a simmer, stirring until the sugar dissolves, about 5 minutes. Remove the pan from the heat and stir in the vanilla beans and bourbon.
Add the cherries. Pour into a sterilized container, seal and let cool to room temperature before refrigerating. Let this steep in the refrigerator for 3 to 4 days before using. (The cherries will keep for about a month.)
Recipe courtesy of chef Kathy Gold, In the Kitchen Cooking School