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Boston Cream Whoopie Pies

Folks, these Boston Cream Whoopie Pies are just the best. I’ve made them a few times over the years and they taste incredibly good. These are best served immediately after assembling. If you are in a time crunch, I would recommend preparing the filling and cake components separately the day before or morning before and waiting to assemble them until absolutely necessary. The reason being the cake can get a little moist the longer these sit.

I am of the opinion that the filling for these whoopie pies is phenomenally tasty. One important note is to use heavy cream in the filling — do not substitute milk, it will not taste anywhere near as good. These are worth the calories of using the cream, trust me.

This recipe makes a bunch. To freeze extras, I would line a baking sheet, place the prepared whoopie pies on the tray and set in the freezer for about an hour for them to get firm. Wrap them individually in cling wrap and store in a large ziploc or tupperware in the freezer. Let them thaw in the fridge on the day you plan serving them. Enjoy!

Don’t they look fantastic?

Boston Cream Whoopie Pies
Makes about 18 pies


  • For the cake component:
  • 1 box yellow cake mix 
  • 3 eggs 
  • 1/2 cup water
  • 1/2 cup oil
  • For the filling:
  • 1 box (3.4 ounce size) vanilla instant pudding (It has to be instant)
  • 1 cup milk
  • 1 cup heavy cream (Do not substitute milk, it won’t be the same)
  • For the glaze:
  • 1 can of chocolate frosting*
  • *Alternatively you can do what I did: Combine 1 cup of chocolate chips with 1 Tablespoon shortening and melt together in the microwave. Heat in 20 sec increments and stir after each session.
  1. Make the cake component: Heat oven to 400. Line a baking sheet with parchment paper.
  2. Mix the cake mix, eggs, water, and oil with an electric mixer on medium speed until well combined. Drop by tablespoonfuls (they spread quite a bit, so just do about 6 to a pan) on parchment lined cookie sheets and bake for about 5-9 minutes, until edges are golden and tops spring back when lightly touched.
  3. Place baking sheets on cooling racks for about 5 minutes, then remove cookies to racks.
  4. Make filling: Whisk pudding mix, milk, and cream in a medium bowl for about 2-3 minutes. Place in refrigerator for 5 minutes to set.
  5. Once cookies have cooled, spread a generous spoonful on the flat side of one cookie and top with the flat side of another.
  6. When all cookies are filled, microwave chocolate frosting for about 20-25 seconds, stopping to stir every 5 seconds or so. You want the frosting to be the consistency of a thick glaze. If it gets too runny, it will drip down the sides of the cookies and make a huge mess.
  7. Spoon the chocolate frosting/glaze on the top of each Whoopie Pie, spreading to almost the edges. Keep any uneaten Whoopie Pies stored in your refrigerator. 
  8. They also freeze very well, just wrap individually with press and seal wrap. To thaw, unwrap and set out on a plate at room temperature.
Recipe from Confessions of a Cookbook Queen.

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  1. What a delicious idea! It makes complete sense to make a boston cream whoppie pie! Now I wish I had one, or maybe two. That would be a balanced dinner, right?