Preheat the oven to 350°F. Line an 8-inch cake pan with parchment paper.
To make the dough: In the bowl of a stand mixer fitted with the paddle attachment, add the butter, brown sugar, and vanilla extract. Mix on low until combined and there’s no butter chunks.
Add in the pumpkin puree and then next, add the dry ingredients: flour, pumpkin spice, baking soda, and sea salt. Mix together until a stiff dough forms.
Add in the chocolate chips and mix to combine completely.
Transfer the dough to the prepared pan. Use your hand and press it out evenly.
Bake for 30 to 35 minutes or until the middle looks set and the edges look dry. Allow to cool completely in the cake pan.
To make the frosting: In the bowl of a stand mixer fitted with the paddle attachment, add the butter, powdered sugar, and vanilla extract. Mix on low until combined and then speed mixer up to high and mix to 2 to 3 minutes or until it’s light and fluffy.
Transfer about half the white frosting to a piping bag with Ateco tip #846.
Divide the remaining frosting in 4 bowls, two of which have just a small amount, about 2 tablespoons maybe. Then, divide the remaining frosting in half.
In one of the small amount bowls, add a pinch of cocoa powder to one and stir in to make chocolate buttercream. Transfer the chocolate to a piping bag with Ateco tip #8 for the stems.
Add a pinch of matcha powder to the other small dish with just a small amount and stir in. Transfer the green to a piping bag with Ateco tip #6 for the vines.
In one of the bowls with more frosting, add a pinch of strawberry powder and stir it in. Add to a piping bag with Ateco tip #21.
For the remaining frosting, add a few drops of India Tree Nature’s Colors Orange dye into the last bowl. You can use a few drops for pastel or more for a darker orange. Transfer to a piping bag with Ateco tip #32.
Starting with the white frosting, pipe a straight line of buttercream on the cookie cake wherever you want your first pumpkin to be. This is the middle of the pumpkin. Then, pipe a slightly curved line on each side of the first line to create the round shape of the pumpkin. These lines should be similar to writing a “C” or the curved part of the “D” as far as shape goes. Continue to do this a few times, anywhere you want a pumpkin on the cake. I made 3 pumpkins on my cake, but you could do more or less or bigger ones or smaller ones.
Next, use the brown and pipe chocolate stems onto the pumpkins.
Add little squiggly lines of green for the vines.
Fill in with rosettes of pink for the flowers by piping a spiral. Last, add dollops of orange for baby pumpkins. And top those with a dollop of the brown for a stem. This can be totally free form so have fun with it!
Store in an airtight container for up to 3 days.