The first time I bit into a whoopie pie, I was visiting Maine and stopped at a small bakery. The soft, cake-like cookies sandwiched around creamy frosting were unlike anything I’d tasted before. When I got home, I knew I had to recreate them with my favorite holiday flavor: gingerbread. These Gingerbread Whoopie Pies combine warm spices, soft molasses cookies, and tangy cream cheese frosting into one irresistible treat.

What makes these special is the perfect balance of flavors. The gingerbread cookies are soft and chewy with just the right amount of spice, while the cream cheese frosting adds a tangy sweetness that cuts through the richness. They’re festive enough for holiday parties but simple enough to make any weekend. Plus, they’re easier than traditional whoopie pies because the cookies are rolled in sugar and don’t require piping.

Why You’ll Love This Recipe

Soft, chewy gingerbread cookies with perfect spice blend
Tangy cream cheese frosting balances the sweet molasses
Easier than traditional whoopie pies with no piping needed
Makes about 12-15 sandwich cookies
Perfect for holiday cookie exchanges
Cookies stay soft for days

Ingredients You’ll Need

For the Ginger Cookies:

3/4 cup unsalted butter, softened – Must be room temperature for proper creaming
1 cup light brown sugar, packed – Creates chewy texture and caramel notes
1 large egg – Binds ingredients and adds moisture
1/4 cup molasses – Gives distinctive gingerbread flavor and dark color
2 1/4 cups all-purpose flour – Provides structure
2 teaspoons baking soda – Creates the signature crackled top
1 teaspoon ground cinnamon – Warm, sweet spice
1 teaspoon ground ginger – The star spice for gingerbread flavor
1/2 teaspoon ground cloves – Adds depth and complexity
1/4 teaspoon fine sea salt – Enhances all the flavors
1/4 cup granulated sugar for rolling – Creates sweet, sparkly coating

For the Cream Cheese Frosting:

4 ounces cream cheese – Must be softened to room temperature
1/4 cup butter – Adds richness to the frosting
1 1/2 cups powdered sugar, plus more as needed – Sweetens and thickens frosting
1/2 teaspoon vanilla extract – Rounds out the flavors

Important: Use unsulphured molasses, not blackstrap molasses, which is too bitter for cookies. Make sure both butter and cream cheese are at room temperature for smooth mixing.

Step-by-Step Instructions

Making the Ginger Cookies:

Preheat and prep: Preheat oven to 375°F (190°C). Line a baking sheet with parchment paper.
Cream butter and sugar: In a stand mixer with paddle attachment, beat softened butter and brown sugar for 1 minute until light and fluffy. Add the egg and beat until smooth. Mix in molasses until fully combined.
Combine dry ingredients: In a medium bowl, whisk together flour, baking soda, cinnamon, ginger, cloves, and salt.
Mix the dough: Add the flour mixture to the butter mixture and stir with a spoon just until combined. Don’t overmix or cookies will be tough. Cover and chill for 10-15 minutes.
Roll in sugar: Place granulated sugar in a shallow bowl. Using a medium cookie scoop (about 1 1/2 tablespoons), scoop dough and roll into balls. Roll each ball in sugar to coat completely.
Shape and bake: Place cookies on prepared baking sheet about 2 inches apart. Lightly flatten the tops with your palm. Bake for 8-10 minutes until edges are set.
Cool: Let cookies cool on the sheet for 5 minutes, then transfer to a cooling rack to cool completely.

Making the Cream Cheese Frosting:

Beat cream cheese and butter: In a medium bowl, beat cream cheese and butter with an electric mixer for 2 minutes until smooth and creamy.
Add sugar and vanilla: Add powdered sugar and vanilla extract. Beat for an additional minute until fluffy. Add more powdered sugar if you prefer thicker frosting.

Assembling the Whoopie Pies:

Pair cookies: Match cookies by size so your whoopie pies look uniform.
Add frosting: Spread or pipe about 2 tablespoons of frosting onto the flat side of one cookie.
Sandwich together: Top with another cookie, flat side down, and gently press to spread the frosting to the edges.
Store: Keep in an airtight container until ready to serve.

Tips for Success

Chill the dough: The 10-15 minute chill makes the dough easier to handle and helps cookies keep their shape better.

Don’t overbake: These cookies should be soft and chewy. They’re done when the edges are set but the centers still look slightly underdone.

Create crackles: For more dramatic crackled tops, bang the baking sheet on the counter right after removing from the oven.

Room temperature ingredients: Both butter and cream cheese must be softened for smooth, lump-free results.

Size consistency matters: Use a cookie scoop to ensure all cookies are the same size so they bake evenly and pair up perfectly.

Let cookies cool completely: Warm cookies will melt the frosting. Wait at least 30 minutes before assembling.

Variations

White chocolate cream cheese: Add 2 ounces melted white chocolate to the frosting for extra richness
Maple frosting: Replace vanilla with maple extract and add 1 tablespoon maple syrup
Extra spicy: Increase ginger to 1 1/2 teaspoons and add 1/4 teaspoon cardamom
Orange zest: Add 1 tablespoon orange zest to the cookie dough for citrus brightness
Chocolate version: Add 1/4 cup cocoa powder and reduce flour by 1/4 cup
Mini whoopie pies: Use 1 tablespoon of dough per cookie for bite-sized treats

Storage

Room temperature: Store assembled whoopie pies in an airtight container for up to 3 days. The cookies will soften slightly, which is actually delicious.

Refrigerator: Keep refrigerated for up to 5 days. The cream cheese frosting stays freshest when cold. Bring to room temperature before serving for best texture.

Freezer: Freeze unfrosted cookies for up to 3 months. Thaw completely before filling. Don’t freeze assembled whoopie pies as the frosting doesn’t freeze well.

Make-ahead: Bake cookies up to 2 days ahead and store in an airtight container. Make frosting and assemble the day you plan to serve.

Frequently Asked Questions

Why did my cookies spread too much?
The dough wasn’t chilled long enough or your butter was too soft. Chill the dough for the full 15 minutes and make sure your butter was softened, not melted.

Can I use regular molasses instead of light?
Regular (dark) molasses works but gives a stronger, more robust flavor. Light molasses is milder and preferred for these cookies.

My frosting is too soft. How do I fix it?
Add more powdered sugar 1/4 cup at a time until it reaches the desired consistency. You can also refrigerate it for 15 minutes to firm up.

Can I make these without a stand mixer?
Yes! Use a hand mixer or even mix by hand with a wooden spoon. It will just take a bit more effort to cream the butter and sugar.

Why aren’t my cookies cracking?
The baking soda creates the cracks. Make sure your baking soda is fresh (not expired) and try the trick of banging the pan on the counter right after baking.

Can I pipe the cookies instead of rolling them?
Absolutely! Transfer the dough to a piping bag and pipe 1 1/2 inch rounds. Skip the sugar rolling step.

Final Thoughts

These Gingerbread Whoopie Pies are everything I love about holiday baking—warm spices, soft textures, and impressive presentation without complicated techniques. The combination of molasses-rich gingerbread and tangy cream cheese frosting is simply perfect. They’re substantial enough to satisfy but not so heavy that you can’t enjoy two (or three).

Whether you’re adding them to a cookie platter, wrapping them as gifts, or enjoying them with afternoon coffee, these whoopie pies deliver festive cheer in every bite. The cookies stay wonderfully soft, and the cream cheese frosting provides just the right balance of sweet and tangy. Make a batch this season and watch them become a new holiday tradition.