Making whoopie (pie) for Valentine’s Day

Yankee Chef logoBy Jim Bailey

Here’s rare treat: A Valentine’s Day Whoopie Pie.

Thank you to Sweetie Pie’s of Dexter, Me., for creating this one just for the Yankee Chef, and thus for our readers. The owner of Sweetie Pie’s was named 2016 Best New Baker as well as the winner of the premier of the Best Yankee Whoopie Pie for 2016.

Although lengthy looking, this recipe is the best of the best when it comes to a red velvet whoopie pie. It’s no wonder she has the best in New England.


1 cup sliced, fresh strawberries
1/4 cup water
1/4 cup sugar
4 cups powdered sugar
1 (8-ounce) package cream cheese, softened
1/2 cup butter or margarine, room temperature
3 tablespoons flour
1 teaspoon vanilla
Pinch of salt


1/4 cup butter or margarine, room temperature
1/4 cup vegetable shortening
1 cup sugar
1 egg
2 teaspoons red icing color gel *
1 teaspoon vanilla
2 1/4 cups flour
1 teaspoon salt
1/2 teaspoon each baking soda and baking powder
1/4 cup Dutch process baking cocoa
1/2 cup sour cream
1/2 cup buttermilk
1/4 cup hot water

In a medium saucepan, bring strawberries, water and sugar to a boil over medium-low heat. Reduce heat and simmer 10 minutes. Remove from heat, transfer to a blender and puree on high until as smooth as possible.

Transfer to a bowl, cover and refrigerate until chilled.

For the cake: Preheat oven to 350-degrees F. In the bowl of a stand mixer, add butter, shortening, sugar, egg, icing gel, vanilla and mix until light and fluffy.

In a separate bowl, mix flour, salt, baking powder, baking soda and set aside.

Add cocoa to the butter mixture and mix on low, scraping down sides of bowl. Once cocoa is incorporated, add sour cream, buttermilk and hot water. Mix on medium low, continuing to scrape sides as needed. Slowly add flour mixture to batter and mix just until smooth, without over-mixing.

Using an ice cream scoop, dollop batter onto parchment-lined cookie sheet about 2 to 3 inches apart. Bake 10 to 12 minutes, or until springy to the touch. Remove from oven, cool slightly before transferring to a rack to completely cool.

Meanwhile, beat cream cheese and butter until smooth. Slowly add powdered sugar, flour and salt until well incorporated. Fold in 1/3 to 1/2-cup chilled strawberry mixture until as thick or as thin as desired for filling. Freeze leftover syrup, as it can be used for frosting, milkshakes and much more. Scoop desired amount of filling onto one cake and top with another.

* I highly suggest using icing gel because of its vibrant results. You are, however, able to substitute liquid food coloring if desired, but it will take at least 1 tablespoon or more.

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Filed Under: Community and Arts LifeThe Yankee Chef

About the Author: Jim Bailey is a third generation Yankee Chef, New England food historian and newspaper columnist. His first cookbook, simply titled The Yankee Chef, has been published. He welcomes all feedback, questions or comments at

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