Chocolate Whoopie Pies

Chocolate whoopie pies are soft, fluffy, and delicious cookie sandwiches. Two homemade chocolate cookies filled with a fluffy vanilla filling make for the ultimate chocolate treat you won’t be able to resist.

With Valentine’s Day coming up soon, my mind is on all things chocolate. Chocolate brownie balls, chocolate stuffed Rolo cookies, and even the healthier chocolate protein balls.

These chocolate whoopie pies are one of my new favorite ways to indulge in a little chocolate treat. They’re soft, fluffy, and absolutely delicious.

Plus, they’re chocolate so they’re great if you’re looking for desserts for Valentine’s Day, something for a holiday treat plate, or baked goods for a girls night or baby shower!

why you’ll love this recipe

• Easy yet impressive – while this recipe seems impressive, especially for someone who’s never made whoopie pies, it’s actually pretty straightforward.
• Fluffy cookies – because of the way you make the cookies for the sandwiches, the cookies stay super soft and fluffy.
• No chill dough – unlike these cut out sugar cookies, you don’t need to chill the dough before baking. This means that these cookies can be ready to go in under 30 minutes from start to finish!

Ingredients

Ingredient Notes

• Buttermilk – if you don’t have buttermilk on hand, you can combine 1 cup milk and 1 tablespoon of either white vinegar or lemon juice together and let it sit for 10 minutes to make your own buttermilk.
• Milk – I always recommend using whole milk in baking recipes since it will give you a creamier result than something with less fat.
• Flour – all-purpose flour works great in this recipe.
• Butter – you want to make sure that the butter is softened before you start making this recipe. Take it out of the fridge and allow it to soften for 30-60 minutes before you get started.

Instructions

There are a number of steps in this recipe, but they’re all pretty simple.

Start by preheating your oven to 325°F and lining a baking sheet with parchment paper or spray with cooking spray. If you have multiple ovens and want to bake cookies at the same time, line two baking sheets.

Start by creaming the butter (or shortening) and sugar. Once creamed, add the egg and mix well.

Next you’ll add the cocoa to the boiling water until it makes a paste, then add the paste to the creamed ingredients and mix well.

Combine the flour, baking soda, baking powder, and salt in a small bowl.

Now alternate adding buttermilk and dry ingredients to the creamed ingredients until they are all incorporated.

You should end up with a pretty, glossy, chocolate cookie batter like you see below.

Next, drop the dough onto the baking sheet by the teaspoon, about 2 inches apart. These need room to expand while baking, so make sure they are spaced out.

You also want to make sure that you’re dropping about the same amount of dough for each cookie. These will be cookie sandwiches, kind of like these homemade moon pies, and you want the sandwich ends to match.

It is okay if the dough isn’t perfectly round, it’ll melt into circles when it’s baking. It’s more important to have about the same amount of dough.

Bake in the preheated oven for 15 minutes t allow to cool completely before filling.

While the cookies are baking, make your filling. To make the filling, put the flour, milk and salt in a double boiler and heat until it combines together to make a paste.

Then cream butter, sugar, and vanilla together. Add the paste to the mixture and beat until light and fluffy.

Place the filling in a piping bag with a large round tip or in a plastic zipper bag with a fairly large piece of the corner cut off for piping.

Once the cookies are cooled, match up cookies to get ones that are as equal in size together. I know I said to get them as even as possible, but you’re inevitably going to end up with ones that are a bit smaller and a bit larger. You want to match these together.

Pipe a swirl (like the pictures below) of filling onto one of the two cookies for each match. Doing the swirl with a bit of space in between parts of the swirl allows the frosting to spread out perfectly when you sandwich the cookies on top of the filling.

This also lets you control the amount of filling and make sure the entire cookie is filled – you want all the filling!

Gently press the top of the chocolate whoopie pies on top of the filled cookie sides.

Let sit for a few minutes then serve!

These are yummy both at room temperature and chilled. I actually personally preferred them chilled, and my husband liked them at room temp. No matter what temperature you serve them, I guarantee they’ll be a huge hit!

Expert Tips

Store any leftover chocolate whoopie pies in the refrigerator. You can either serve chilled or remove them from the fridge about 30 minutes before serving to allow them to come to room temperature. Cookies should be enjoyed within 5 days.

Stir constantly to make sure that the mixture doesn’t burn as you are mixing to create the chocolate paste.

Use a teaspoon measuring spoon to measure out the cookies to keep them about the same size.

Recipe FAQs

More Easy Cookies

If you like these chocolate whoopie pies, you’ll love these other cookie recipes!

• Peanut butter blossoms – these soft and fluffy peanut butter cookies are topped with a chocolate kiss, they’re a classic favorite!
• Orange sugar cookies – traditional sugar cookies with a slight hint of citrus flavor, these are popular for baby showers, bridal showers, and with both kids and adults!
• Sugar cookie bites – delicious sugar cookies in bite-size form! They’re cute, delicious, and great for sharing with a crowd.
• Cherry cheesecake cookies – sugar cookies, cheesecake, and cherry pie all combined into one delicious treat!
• Chocolate chip pudding cookies – a chocolate lover’s dream! Chocolate cookies with chocolate chips all melted and gooey inside.