Pumpkin Bread

1. Preheat the oven to 350F and coat the inside of a 9×5 loaf pan with nonstick spray. Line with parchment paper.
2. In a large bowl, whisk together the pumpkin, brown sugar, maple syrup, oil, egg, and vanilla.
3. Once smooth, whisk in the baking soda, baking powder, salt, pepper, pumpkin pie spice, and cinnamon.
4. Once those are evenly mixed into the batter, whisk in the flour.
5. Pour into the pan and spread even. Bake for 28 to 32 minutes or until a toothpick comes out clean with a few moist crumbs.
6. Allow to cool at room temperature for about 15 minutes, then lift out of the pan and onto a plate or cooling rack and store in the refrigerator until completely cooled, about 45 minutes.

Pumpkin Pudding

1. While the pumpkin bread cools, start on the pudding.
2. In a medium saucepan, whisk together the sugar, cornstarch, cinnamon, and salt.
3. Slowly whisk in the milk until smooth, then whisk in the egg yolks and pumpkin.
4. Place over medium heat and continue to whisk until thickened. It’s important to keep whisking to prevent any lumps. This will take about 10 minutes and it will go from liquid to thick very quickly, so keep a close eye on it once it starts to steam.
5. Once thickened, remove from heat transfer to a large bowl. Cover the surface of the pudding with plastic wrap and chill in the refrigerator for at least 30 minutes or until the pumpkin bread is also cooled.
6. After those 30 minutes, add the cream cheese and powdered sugar to a large bowl fitted with the whisk attachment. Whip on medium-high speed until smooth.
7. With the mixer on medium speed, slowly trickle in the heavy cream. Mix in enough to thin out the cream cheese, scraping down the bowl throughout this process and mixing to prevent lumps. Once the cream cheese is thin enough, pour in the rest of the heavy cream and crank to high speed. Whip until you reach firm peaks, about 3 minutes. Don’t walk away from the mixer as we don’t want to overwhip. 
8. Scoop a little less than half of the whipped cream into the cooled pudding (it’s ok if it’s still a little warm) and use a whisk to gently fold to combine.
9. Now spread a thin layer of the pudding into the bottom of an 8×8 pan, or anything of similar size. 
10. Cut the pumpkin loaf in half hotdog style, then chop width-wise into 22 pieces, 11 for each half. 
11. Lay 11 pieces of the pumpkin bread over the thin layer of pudding, then spread half of the remaining pudding on top.
12. Lay another 11 pieces of pumpkin bread and cover with the remaining pudding. Then finish it off with a final layer of the remaining whipped cream.
13. Top with a light dusting of cinnamon. Chill overnight (uncovered) and tomorrow, dig in!