Heat oven to 325. Cut loaf of pumpkin bread into cubes and place on baking sheet. Bake until toasted, about 15-20 minutes. Set aside. Prepare a 9 x 13 inch baking pan with butter, and scatter toasted pumpkin bread cubes across bottom.
In a medium saucepan, combine heavy cream, milk and vanilla bean paste. Bring to a simmer and set aside. In a large bowl combine eggs, maple syrup, pumpkin and whisk together.
Slowly whisk the cream mixture into the egg mixture, then add the Bourbon.
Add the chocolate chips and the dried cranberries, mix well.
Pour the custard mixture over the pumpkin cubes and let sit for 15 minutes to soak in. Press down on the cubes to submerge.
Place the pan into a larger roasting pan and then pour hot tap water into the large roaster until it comes half-way up the sades of the pan containing the custard mixture.
Bake in the water bath until the sides are slightly puffy and the center jiggles, about 1 hour.
Remove pan from water bath and let cool for at least 30 minutes before serving.
Slice bread pudding and drizzle with melted white chocolate, and caramel then garnish with cranberries and dark chocolate chips.