Introduction

These Boston Cream Pie Cookies offer a delightful twist on the classic dessert by transforming its iconic flavors into a handheld treat. With soft cookies sandwiching a rich whipped cream filling and topped with a smooth chocolate glaze, they’re perfect for any occasion.

A close-up view of a stack of three thick, round pancakes, each pancake separated by a smooth, shiny layer of dark chocolate glaze. The top pancake is fully covered with the same glossy chocolate glaze, and the center is decorated with small, textured chocolate pieces and sprinkled with white sugar crystals. The pancakes have a golden-brown edge with a soft, light beige interior. They sit on a white plate, which rests on a white marbled surface. The image is sharp on the top pancake, slightly blurred towards the bottom and background, photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
2 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon baking soda
1/4 teaspoon salt
1 cup heavy cream
1/2 cup powdered sugar
1 teaspoon vanilla extract (for the cream filling)
1 cup semi-sweet chocolate chips
1 tablespoon vegetable oil

Instructions

Step 1: In a large mixing bowl, cream together the softened butter and granulated sugar using an electric mixer on medium speed until light and fluffy, about 3-4 minutes.
Step 2: Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract until fully combined.
Step 3: In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until just combined. Avoid overmixing.
Step 4: Cover the dough and refrigerate for at least 30 minutes.
Step 5: In a medium bowl, whip the heavy cream with powdered sugar and vanilla extract using a hand mixer until stiff peaks form, about 3-5 minutes. Keep the cream in the refrigerator until ready to use.
Step 6: Preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
Step 7: Drop rounded balls of dough onto the prepared sheets about 2 inches apart, using a cookie scoop or tablespoon.
Step 8: Bake for 10-12 minutes until edges are lightly golden; centers may look slightly underbaked.
Step 9: Let cookies cool on baking sheets for 5 minutes, then transfer to a wire rack to cool completely.
Step 10: Melt chocolate chips and vegetable oil in a microwave-safe bowl in 30-second intervals, stirring until smooth.
Step 11: Allow chocolate to cool slightly, then spread a dollop of whipped cream filling on the flat side of one cookie and sandwich it with another cookie, pressing gently.
Step 12: Dip or drizzle assembled cookie sandwiches with melted chocolate and place on a wire rack to set.

Tips & Variations

For extra flavor, add a teaspoon of instant coffee granules to the whipped cream to mimic the classic Boston Cream Pie coffee note.
Try using dark chocolate instead of semi-sweet for a richer glaze.
Chill the dough longer or overnight for easier handling and better texture.
Use a piping bag to fill cookies neatly with whipped cream, preventing mess.

Storage

Store assembled cookies in an airtight container in the refrigerator for up to 3 days to keep the cream filling fresh. Let them come to room temperature for 10-15 minutes before serving. If stored without cream filling, the cookies keep well at room temperature for up to 5 days.

How to Serve

A stack of two thick round donuts with light golden brown edges, each covered in a smooth, glossy dark chocolate glaze that drips slightly down the sides. The top donut has small white sugar crystals sprinkled over the chocolate, adding texture and contrast. The donuts sit on a white plate with a fine rim, which rests on a white marbled surface. The chocolate coating is rich and shiny, creating a lovely shine under soft lighting. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I make the cookie dough ahead of time?

Yes, cookie dough can be prepared and refrigerated for up to 24 hours before baking. Just cover it well to prevent drying out.

How do I prevent the whipped cream filling from becoming runny?

Ensure you whip the cream until stiff peaks form and keep it chilled until assembly. Adding powdered sugar stabilizes the cream slightly, but use the filling within a few hours for best texture.