Preheat your oven to 350°F (175°C). Lightly grease a mini muffin tin or line it with paper liners for easy removal.
In a large bowl, combine 1 cup pumpkin puree, 1/2 cup granulated sugar, 1/4 cup brown sugar, and 1/2 cup vegetable oil. Whisk until smooth. Add the two large eggs and 1 teaspoon vanilla extract, then whisk again until fully incorporated.
In a separate bowl, sift together 1 cup all-purpose flour, 1/2 cup unsweetened cocoa powder, 1 teaspoon baking powder, 1/2 teaspoon baking soda, 1/2 teaspoon salt, 1 teaspoon ground cinnamon, 1/2 teaspoon ground nutmeg, and 1/4 teaspoon ground ginger.
Gradually add the dry ingredients into the wet mixture, folding gently with a spatula until just combined. Fold in the 1/2 cup chocolate chips.
Spoon the batter evenly into the prepared mini muffin pan, filling each cup about 3/4 full. Bake for 15-18 minutes or until a toothpick inserted in the center comes out mostly clean with a few moist crumbs.
Allow the bites to cool in the pan for 10 minutes, then transfer to a cooling rack to cool completely before topping.
In a chilled bowl, pour 1 cup heavy whipping cream. Add 2 tablespoons powdered sugar and 1/2 teaspoon vanilla extract. Whip on medium-high speed until soft peaks form.
Once the brownie bites are cool, dollop or pipe the whipped cream on top. Optionally sprinkle a pinch of cinnamon or cocoa powder on the whipped cream. Serve immediately or refrigerate until ready.