Begin by preheating your oven to 350 degrees F.
Prepare your baking pan by spraying it with baking spray. Then, use a pastry brush to make sure all the nooks and crannies of the pan are coated with the spray. Set aside.
In the bowl of a stand mixer, cream together the brown sugar and butter. Add the eggs and vanilla and beat again until smooth.
In a medium bowl, whisk together the flour, baking powder, cinnamon, and salt. Add half of this mixture to your sugar and butter mixture. Start to combine for a few seconds, and then add in your buttermilk. Combine for a few more seconds and then add in the rest of your flour mixture. Finally, add in the finely shredded carrots and mix until just combined.
Use a teaspoon to fill each cavity 3/4 full of batter. Do not overfill. Lightly bang pan on counter to level the batter.
Bake for 14-16 minutes or until the center is set and the edges begin to brown. Allow the cakes to cool in the pan for 5-8 minutes before inverting onto a cooling rack. Clean your pan and repeat with the remaining batter.
Next, prepare your glaze. In a medium-sized bowl, start with the confectioners' sugar. Then, add the half and half one tablespoon at a time to reach the desired consistency. Whisk to combine. Mix in the vanilla extract and optional food coloring.
Whisk well until the glaze is smooth and no sugar clumps are visible.
Once your cakes have cooled, use a pastry bag to drizzle each cake with the confectioners' sugar glaze. Allow the glaze to set before styling on top of crushed chocolate graham cracker crumbs.