1. Preheat the oven to 350 F and line a 9×5″ loaf pan with parchment paper and/or spray with non-stick cooking spray.
2. In a large mixing bowl, whisk together the flour, baking powder, baking soda, cinnamon, nutmeg, all-spice and salt. In another large bowl, lightly beat the eggs, then whisk in the oil, and both sugars. Add the pumpkin puree and stir thoroughly. Slowly add the dry ingredients to the wet, stirring until just combined. Pour the batter into the prepared loaf pan and place into the pre-heated oven for 50-55 minutes, or until a toothpick inserted in the center comes out clean.
3. Allow the loaf to cool for 10 minutes in the pan before removing and cooling completely on a wire rack. Once cooled, slice the loaf into 1″ slices. Using your chosen cookie cutter, cut out the shapes and place them on a baking sheet prepared with parchment paper or a silicone baking sheet. Place the shapes in the freezer for 1 hour.
4. During the last 15 minutes of freezing time, prepare the chocolate loaf batter. Preheat the oven to 350 F and prepare another 9×5 loaf pan by lining with parchment paper and/or spraying with non-stick spray.
5. Combine the dry ingredients together in a mixing bowl. In the bowl of a stand mixer fitted with the paddle attachment, or using an electric mixer, beat the butter on high until soft and fluffy, about 1 minute. Add in both sugars and beat until fluffy, 1-2 minutes. Add the eggs one at a time, and then the vanilla extract, beating in between.
6. Add half of the dry ingredients to the wet ingredients, with the mixer running on low. Add half of the milk, then the remaining dry ingredients, slowly mixing together. Add the remaining milk and mix on low until well combined.
7. Remove the frozen cut-outs from the freezer. Add just enough chocolate batter to the prepared loaf pan to cover the bottom. Line up the frozen cut-outs in the center of the pan, leaving 1 to 2″ at each end of the pan (you may have a few cut-outs leftover). Pour the remaining batter evenly over the top of the cut-outs, ensuring the pumpkin loaf is covered. Place the pan in the oven for 50-55 minutes, or until a toothpick inserted in the center comes out clean.
8. Cool the loaf in the pan for 10 minutes, before removing and cooling completely on a wire rack. Slice, and serve.

Loaf will keep at room temperature, in a sealed container for 3-4 days, or 6-7 days in the fridge. The loaf can also be frozen (once cooled) for up to 2 months.