Pumpkin Molasses Whoopie Pies

These little clam-like cookie sandwiches are apparently called whoopie pies – and what a delightful name. Upon investigation of the name origin, it seems the Amish were very fond of using up leftover cookie batter (I’ve personally never heard of having leftover anything when baking cookies – it all gets used) and Amish bakers turn the leftover dollops into these cream-filled drops of happiness. The story gets even better, though, because the name Whoopie Pie is said to come from the exclamation of joy each child makes if one of these treats is found in said child’s lunch box. Thanks to the Amish for these things and for Amish children for contributing a truly light-hearted name to what has become a classic baked good.

When doing recipe research, there were dozens of recipes for pumpkin whoopie pies, which all looked fantastic, but I wanted to put a spin on the plain cakey pumpkin cookies and see if I couldn’t make these gluten free pies a bit more reminiscent of the deeply comforting pumpkin oat molasses cookies we used to make when I was a kid. They’re heavy with the tang of molasses, which pairs perfectly with soft, subtle pumpkin, and the oats add a nuttiness that just exudes fall in every bite. I modified the cookie recipe a bit to create flatter, wider cookies more conducive to being sandwiched together with cream cheese buttercream, and piped them out to create similarly-sized dollops for the final creation. And it worked! These are just a touch sweet, with most of the sweetness hidden in the cream cheese filling, and are deep dark molasses brown, which differs from the peppy pumpkin orange of others. But they’re also one of my new favorite cookie combos – light enough that they feel like a gust of fall air, but dense enough with spices and sweet tangy blackstrap that you feel like donning plaid and chopping wood to celebrate the season.

These are some of the easiest pumpkin treats you can toss together, and they’re impressive for a company potluck, kid’s treat day in class, or just a great tray to have around for a movie night one of these fall evenings. Honestly, most pumpkin treats are fairly easy, but why not go for these little guys to add a bit of Whoopie! to your day. Do what tastes good!

Print Recipe

5 from 1 vote

Gluten Free Pumpkin Molasses Whoopie Pies

Cream-filled pumpkin and molasses cookies

Prep Time30 minutes mins

Cook Time15 minutes mins

Course: Dessert, Snack

Cuisine: American

Diet: Gluten Free

Keyword: cream cheese, molasses, pies, pumpkin, whoopie

Servings: 32 whoopie pies

Calories: 100kcal

Author: Amelia Farber

Equipment

• Cookie sheet
• Piping bag and piping tips

Ingredients

For the cookies:

• 1 Cup gluten free flour 1-1 mix with xanthan gum
• 1/2 Cup arrowroot starch
• 1/2 Cup almond flour
• 1 tsp baking soda
• 1 tsp baking powder
• 1/2 tsp salt
• 1 Cup gluten free quick oats
• 1 Cup canned pumpkin puree
• 3/4 Cup packed brown sugar
• 1/2 Cup molasses
• 1/2 Cup canola oil
• 2 eggs
• 1 tsp vanilla extract
• 1/2 tsp ginger
• 1 tsp cinnamon
• 1/4 tsp each: ground cloves and nutmeg

For the filling:

• 1 8-oz package cream cheese room temperature
• 1/2 Cup butter room temperature
• 1/2 Cup powdered sugar
• 1/2 tsp vanilla extract

Instructions

• Preheat the oven to 350° Fahrenheit. Grease two cookie sheets and line with parchment paper, then spray or grease the parchment paper. In a medium bowl, whisk together the dry cookie ingredients (the flour, starch, almond flour, baking soda and powder, salt, and oats). Set aside. In a larger bowl, whisk together the wet ingredients (pumpkin, brown sugar, molasses, oil, eggs, vanilla and spices). Dump the dry ingredients into the wet ingredients and use a spatula to mix until combined. Spoon or pipe your cookies onto your cookie sheets – about 2 teaspoons per cookie, flattened a bit (they will not spread) to be 1.5-2 inches in diameter. Fill each sheet with about 20 cookies then pop in the oven for 15 minutes. Continue making cookies until batter is all used.
• Make the filling while the cookies bake and cool. In a medium bowl, using an electric mixer, beat together the butter and cream cheese for about a minute until fluffier and creamy.  Add in the vanilla and powdered sugar and continue to beat until softened and combined. Flip all of your cooled cookies to prep for filling. Spoon the filling into a piping bag and pipe filling to cover the underside of 1/2 of all of the cookies, or simply spoon the filling onto the cookie halves. Pair filled and unfilled cookies and press together to make your whoopie pies. Eat immediately! Or save for later – whatever you have the strength to do.

Tag @sisterssansgluten on Instagram if you snap a photo of your whoopie pies!

Food photography and styling by Amelia Farber