1. Adjust the oven rack to the middle position and preheat oven to 350°F. Line a muffin tin with 10 paper or foil liners, and set aside.
2. Whisk flour, cinnamon, baking powder, baking soda, salt, allspice, and ginger together in a medium bowl.
3. In a separate large bowl, whisk the brown sugar, pumpkin puree, olive oil, and eggs until smooth. Using a rubber spatula, add the dry ingredients to the wet ingredients and stir gently until just combined, with no streaks of flour remaining.
4. Divide the batter evenly into prepared muffin tin, filling each about two-thirds full. Bake until a toothpick inserted into the center comes out clean, about 15 to 20 minutes, rotating muffin tin halfway through baking.
5. Let cupcakes cool in the muffin tin for 10 minutes, then transfer to a wire rack and let cool completely.

For the whipped cream (optional topping)

1. In a large bowl using a stand or handheld mixer with the whisk attachment, whip the heavy cream, sugar, and vanilla extract on medium-high speed until stiff peaks form, about 2 to 3 minutes. Pipe or spoon the whipped cream onto the cooled cupcakes, and serve immediately.