Best Whoopie Pies

Whoopie pies are technically two cakes pretending to be a cookie, with a marshmallow filling in the middle that sticks to your fingers and your memory. This version sticks to the New England original: cocoa-rich cakes with a fluffy marshmallow filling, no fancy substitutions. Shortening keeps the cakes pillowy and gives them that signature soft, almost spongy bite that butter alone can’t quite match.

The glass-bottom flatten trick after dropping the dough is what gives them that classic round, even shape. Skip it and you’ll get craggy mounds that bake unevenly and refuse to sandwich properly.

Don’t overbake. Eight minutes is the sweet spot. The cakes should spring back lightly when touched but still look matte on top, never crisp at the edges. They keep softening as they cool, and a slightly underbaked center is what you want for that pillowy texture.

Pro Tips

• Cool the cakes completely before filling. Warm cakes melt the marshmallow filling into a runny mess.
• Match the cakes by size before sandwiching, otherwise some pies will smush and some won’t seal.
• Store assembled pies in a single layer with parchment between, in an airtight container at room temp for up to 3 days.

Variations

• Add a teaspoon of espresso powder to the cake batter to deepen the chocolate flavor.
• Swap the marshmallow filling for peanut butter buttercream.
• Use red velvet batter instead of chocolate for a holiday-ready version with cream cheese filling.