Stewart and I went apple picking a couple weeks ago, and in the little farm store we saw pumpkin whoopie pies. Stewart asked if I would make them, and when I said yes, he bought a sugar pumpkin to increase the chances of me keeping my promise.

I’ll be the first to admit that these aren’t perfect. Don’t get me wrong, they’re really really tasty, but the verdict is that they’re not exactly like traditional whoopie pies. I need to work on the batter recipe, because these are more like soft cookie pies than whoopie pies. I think with an even softer, spongier batter, we’ll be in business, but these are perfectly serviceable cookie-whoopie pies if you want to give the initial test recipe a shot.

I used homemade pumpkin puree, but the canned stuff will work fine. The homemade version is easy, but obviously more time consuming than opening up a can. As far as I can tell, the only difference between the canned puree and the homemade is the color. Homemade pumpkin puree is considerably lighter and brighter. I’ll include the preparation for the puree at the end of the post.

Pumpkin Whoopie Pies
Makes 18-24 Small Pies (36-48 pieces)

1/2 Cup Non Hydrogenated Vegetable Shortening
2 Cups Sugar
2 tsp Molasses
2 tsp Vanilla Extract
1 1/2 Cups Pumpkin Puree
4 1/2 Cups All Purpose Flour
1 Tbs Ener-G Egg Replacer
1 tsp Baking Soda
1 tsp Baking Powder
1 tsp Salt
1/4 tsp Nutmeg
1/4 tsp Allspice
1/4 tsp Cinnamon

Preheat oven to 375º. Line two cookie sheets with parchment paper.

Cream shortening and sugar together, using a stand mixer if available. You can also do it by hand. Add molasses and vanilla and beat well. Add pumpkin puree and whip until incorporated (don’t worry if the fat doesn’t mix in completely).

In a separate bowl, combine all the remaining ingredients and mix well. Add this dry mix to the wet until all incorporated. It will make a stiff batter.

I find it easiest to use and ice cream scoop that has a release lever to drop the dough onto your cookie sheet. The scoop I used holds 2 Tbs.

Wet your fingers and gently flatten the dough balls. This will prevent your pies from tipping over by creating a semi-flat surface for them to rest on.

Bake for 10-13 minutes or until a toothpick inserted comes out clean, and the tops spring back when pressed in the center.

Remove cookies from the cookie sheet as soon as they come out of the oven to prevent over-baking. Cover them with a towel or plastic wrap to keep moisture/steam in, as this will prevent a hard crust from forming. Prepare the filling while your cookies are cooling.

Cream Cheese Filling

1/2 Container Tofutti Better than Cream Cheese
2 Cups Powdered Sugar
2 Tbs Earth Balance

Whip ingredients together until smooth. Set aside or refrigerate until use.

I put my filling in a zip-top bag and sliced off the corner to pipe the filling into the center. You don’t need that much filling per pie. Make sure the sides of the cookies that were touching the cookie sheet are the side that touch the filling.

Traditional whoopie pies are chocolate. I think these would be awesome with some mini chocolate chips mixed in, or perhaps some melted chocolate drizzled over the top. Store them wrapped in plastic wrap or in an air-tight container to keep them soft.

If you’d like to read about how to make your own pumpkin filling, click the link below the last photo!

Homemade Pumpkin Puree
Makes 3-4 Cups

1 Sugar Pumpkin, 3-4 pounds
1-2 Cups Water

Preheat oven to 400º F.

Slice pumpkin in half. Scoop out the seeds and strings–if you’d like to save the seeds, place the seedy pulp large bowl and set aside, otherwise discard it. Place pumpkin cut-side-down on a rimed cookie sheet or inside a large roasting pan. Add 1-2 Cups of water and bake for 90 minutes, or until flesh is very soft and the skin has darkened. Scoop out the soft flesh into the work bowl of a food processor and blend until smooth.

Tip for Seeds
Place the pulp and seeds in a large bowl and cover with a generous amount of water. Squeeze the pulp to separate it from the seeds. The seeds will float. Use a slotted spoon to skim the seeds from the top of the water. Dry the seeds well and roast and season if desired.