Pumpkin Whoopie Pies with Fluffy Vanilla Filling

Halloween was three days away, and Clyde had a plan. He would sell treats from the kitchen window, the way he always does, only spookier. He had even tied an orange ribbon around his ears. “I need something round, orange and soft,” he said, sticking his head in as far as it would go. “And sweet in the middle.” Gerzsi looked at the pumpkin on the shelf. Whoopie pies it was.

Whoopie pies are an old American treat from Pennsylvania and New England: two soft little cakes with a creamy filling squeezed in between. Gerzsi put the shortening and brown sugar in the mixer and switched it on. The recipe said five to seven minutes. After one minute he wanted to stop. Clyde counted out loud from the window, very slowly, all the way to seven. By then the mixture was pale and fluffy, and Gerzsi had to admit it looked much better.

In went the eggs, the vanilla, the spices and the pumpkin. Gerzsi scooped little mounds onto the baking sheets and pressed each one flat with the back of a spoon. Ten minutes later the kitchen smelled of cinnamon and ginger, and two dozen orange domes were cooling on the rack. Clyde reached for one. Gerzsi moved the rack.

Then came the filling. Gerzsi had cooked the milk and flour into a thick paste, and it was still steaming in the saucepan. He was about to scrape it straight into the bowl of shortening and sugar. Chef Tamás picked up the saucepan, put a lid on it and set it in the fridge. Then he pointed at the recipe card: cool completely. Half an hour later, the cold paste went in, the mixer ran for seven minutes, and the filling came out light as a cloud.

Gerzsi spread the filling on the flat side of half the cakes and pressed the rest on top. Clyde sold the first one to himself. Then the second. “Quality control,” he said, and he set the rest out in the window in a neat orange row.

Why this one works

Beating the shortening and brown sugar for several minutes traps air, so the cookies bake up soft and cakey instead of flat. Canned pumpkin brings moisture and color, and the shortening keeps the crumb tender. The filling starts with a cooked milk and flour paste, which makes it fluffy and less sweet than a plain sugar frosting.

Pumpkin Whoopie Pies with Fluffy Vanilla Filling

• Servings: 24 sandwich cookies
• Prep Time: 30 minutes
• Cook Time: 10 minutes per batch
• Time: 1 hour 30 minutes, including chilling
• Difficulty: Easy
• Print

Soft pumpkin and brown sugar cookies with ginger and cinnamon, sandwiched around a light, cooked vanilla filling.

Ingredients

For the cookies
• 1 cup (190 g) shortening
• 2 cups (400 g) packed brown sugar
• 2 large eggs, at room temperature
• 1 teaspoon vanilla extract
• 3 1/2 cups (440 g) all-purpose flour
• 1 1/2 teaspoons baking powder
• 1 1/2 teaspoons baking soda
• 1 teaspoon salt
• 1 teaspoon ground cinnamon
• 1 teaspoon ground ginger
• 1 1/2 cups (about 370 g) canned pumpkin puree
For the filling
• 1/4 cup (30 g) all-purpose flour
• A pinch of salt
• 3/4 cup (180 ml) 2% milk
• 1 cup (190 g) shortening
• 2 cups (240 g) confectioners’ sugar
• 2 teaspoons vanilla extract

Directions

1. Start the filling base first: In a small saucepan, mix the 1/4 cup flour with the pinch of salt. Whisk in the milk a little at a time until there are no lumps. Bring it to a boil over medium-high heat, then turn the heat to medium and keep stirring for about 2 minutes, until thick. Cover and chill until it is cold all the way through.
2. Heat the oven to 400°F (200°C) and grease two baking sheets.
3. Cream: Beat the shortening and brown sugar for 5 to 7 minutes, until pale and fluffy. Add the eggs one at a time, beating after each, then the vanilla.
4. Dry mix: In another bowl, whisk the flour, baking powder, baking soda, salt, cinnamon and ginger.
5. Dough: Add the dry mix to the creamed mixture in parts, taking turns with the pumpkin, and mix until smooth. If the dough looks soft, chill it for 30 minutes so the cookies spread less.
6. Bake: Drop rounded tablespoons of dough onto the sheets, 2 inches (5 cm) apart, and press each one down a little with the back of a spoon. Bake for 10 to 11 minutes. Move the cookies to wire racks and let them cool completely.
7. Finish the filling: Beat the shortening, confectioners’ sugar and vanilla until smooth. Add the cold milk paste and beat for about 7 minutes, until light and fluffy.
8. Assemble: Spread filling on the flat side of half the cookies and press the other halves on top. Keep them in the fridge.

Fresh pumpkin puree works too, but drain it well first, or the cookies turn heavy.
For a tangier filling, swap half of the filling shortening for cream cheese.
Whoopie pies keep in an airtight container in the fridge for up to 5 days. To freeze, wrap each one in plastic wrap and then foil, freeze for up to 3 months and thaw in the fridge.

🛒 Worth buying for this recipe

• KitchenAid Classic Series 4.5-Quart Tilt-Head Stand Mixer. America’s Test Kitchen’s best mid-priced stand mixer. It creams the dough and whips the filling while your hands are free. About $323 on sale at the time of their review. See it on Amazon
• KitchenAid Artisan Series 5-Quart Stand Mixer. Recommended by America’s Test Kitchen, with a bigger bowl for double batches. Check price. See it on Amazon
• Breville Handy Mix Scraper. The winner of America’s Test Kitchen’s hand mixer test. It was the fastest at creaming and handled dense cookie dough easily. About $160 at the time of their review. See it on Amazon
• Cuisinart Power Advantage Plus 9-Speed Hand Mixer. America’s Test Kitchen’s Best Buy hand mixer: fast, with the simplest controls in the lineup and a storage case. About $79 at the time of their review. See it on Amazon
• OXO Good Grips Medium Cookie Scoop. America’s Test Kitchen’s best 1.5-tablespoon scoop. Every mound comes out the same size, so every top finds a matching bottom. About $18 at the time of their review. See it on Amazon
• Vollrath Wear-Ever Aluminum Cookie Sheet. The winner of America’s Test Kitchen’s cookie sheet test. Thick aluminum that bakes evenly and didn’t warp. It is a bit heavy and scratches. Check price. See it on Amazon
• Checkered Chef Cooling Rack. America’s Test Kitchen’s favorite half-sheet wire rack, for cooling two dozen cakes at once. About $28 at the time of their review. See it on Amazon

How Chef Tamás makes it

Chef Tamás makes these with pumpkin he roasts himself instead of canned puree, and he fills them with a cream cheese or mascarpone cream.

🧰 Tools we use

Tamás didn’t name brands for this one. The linked models are America’s Test Kitchen’s picks for the same jobs.

• A stand mixer. See the ATK pick on Amazon
• A hand mixer. See the ATK pick on Amazon
• A cookie scoop. See the ATK pick on Amazon
• Parchment paper or a silicone baking mat.

💡 Chef Tamás’s tricks

• Scoop every cookie the same size.
• Don’t overbake them. Take them out while they are still soft.
• Whip the filling only when the cooked base is completely cold.
• The most common mistakes he sees: overbaked, dry cookies, and a runny filling because the base was still warm.
• How he serves them: with toasted pumpkin seeds, or with pumpkin seed oil or pumpkin seed spread. They are also a good fit for a Halloween party for kids.
• He serves them as a dessert on his restaurant menu.

Adapted from Pumpkin Whoopie Pies on Taste of Home. Cooked our way at the inn.

Sources

• Taste of Home: Pumpkin Whoopie Pies (recipe by Deb Stuber)
• America’s Test Kitchen: The best stand mixers
• America’s Test Kitchen: The best hand mixers
• America’s Test Kitchen: The best portion scoops
• America’s Test Kitchen: The best cookie sheets
• America’s Test Kitchen: The best wire racks