Brown Sugar Pop Tart Cookies – A Nostalgic Treat with a Chewy Twist.

If you grew up eating brown sugar cinnamon Pop-Tarts, you know exactly how comforting that sweet, cinnamon-spiced filling tastes. These Brown Sugar Pop Tart Cookies capture that same nostalgic flavor — but in the form of thick, chewy cookies with gooey brown sugar centers and a simple cinnamon glaze on top.

I came up with this recipe after stumbling upon a box of Pop-Tarts tucked away in the back of the pantry. Instead of toasting them, I started thinking about how that signature cinnamon-brown sugar filling could be reimagined. The result? Soft cookies with buttery brown sugar dough, a ribbon of cinnamon filling tucked inside, and a sweet glaze drizzled over the top. They taste like childhood, but upgraded — soft, chewy, and far more homemade.

They’ve become a fast favorite in my kitchen. Whether you’re baking them for a party, sharing with friends, or just enjoying one with a cup of coffee, these cookies hit the perfect balance between cozy and playful.

Ingredients

For the Cookie Dough

1 cup (2 sticks) unsalted butter, softened
1 cup packed light brown sugar
½ cup granulated sugar
2 large eggs
2 tsp vanilla extract
3 cups all-purpose flour
1 tsp baking soda
1 tsp baking powder
½ tsp salt
2 tsp ground cinnamon

For the Cinnamon Filling

½ cup packed light brown sugar
1½ tsp ground cinnamon
1 tbsp all-purpose flour
1½ tbsp melted butter

For the Glaze

1 cup powdered sugar
1½ tbsp milk (plus more as needed)
½ tsp ground cinnamon
½ tsp vanilla extract

Instructions

Step 1: Preheat the Oven

Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.

Step 2: Make the Cinnamon Filling

In a small bowl, mix together the brown sugar, cinnamon, flour, and melted butter until it forms a thick, sandy paste. Set aside — this will be spooned into the center of each cookie to mimic the Pop-Tart filling.

Step 3: Cream the Butter and Sugars

In a large mixing bowl (or using a stand mixer), beat the softened butter, brown sugar, and granulated sugar together on medium speed until light and fluffy, about 2–3 minutes.

Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.

Step 4: Add Dry Ingredients

In a separate bowl, whisk together the flour, baking soda, baking powder, salt, and cinnamon.

Gradually add the dry mixture to the wet ingredients, mixing on low until just combined. The dough should be soft but not sticky. If it feels too sticky to scoop, chill it for 15–20 minutes.

Step 5: Fill and Shape the Cookies

Use a medium cookie scoop (about 2 tablespoons of dough) and place half of the scooped dough balls onto the prepared baking sheets.

Flatten each slightly with your fingers, creating a shallow well in the center. Spoon about ½ teaspoon of the cinnamon filling into each well.

Take another scoop of dough, flatten it slightly, and place it on top of the filling, sealing the edges gently so the filling is enclosed inside. Roll gently into a smooth ball. Repeat with remaining dough and filling.

Step 6: Bake

Bake the cookies for 10–12 minutes, or until the edges are set and the tops are just beginning to turn golden. The centers should still look soft — they’ll continue to set as they cool.

Let the cookies rest on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Step 7: Make the Glaze

In a small bowl, whisk together powdered sugar, milk, cinnamon, and vanilla until smooth. The glaze should be thick but pourable. Add a splash more milk if needed to reach drizzling consistency.

Step 8: Glaze the Cookies

Once the cookies are fully cooled, drizzle or spread the glaze over the tops. Let the glaze set for about 15 minutes before serving.

Flavor & Texture Notes

These Brown Sugar Pop Tart Cookies are soft, thick, and buttery with a chewy interior. The brown sugar and cinnamon give the dough a warm, cozy sweetness that pairs perfectly with the gooey filling inside.

The filling itself is a nod to that classic Pop-Tart flavor — brown sugar-rich, warmly spiced, and just a bit molten when the cookies are still warm. The glaze adds a thin, sweet layer that finishes each bite with that familiar cinnamon frosting taste.

It’s everything you loved about a Pop-Tart, but in the form of a bakery-style cookie that feels homemade and elevated.

Tips & Variations

Chill for Thicker Cookies: If you prefer extra-thick cookies, chill the filled dough balls for 30 minutes before baking.
Make Them Jumbo: Use a large scoop and double the filling for oversized bakery-style cookies. Adjust bake time to 13–15 minutes.
Filling Options: Swap the cinnamon filling for jam (strawberry or raspberry) to mimic fruit Pop-Tarts.
Glaze Flavors: Add a pinch of nutmeg or use maple extract in the glaze for a fall-inspired twist.
Sprinkles: For a fun nostalgic touch, add a few rainbow sprinkles on top of the glaze, just like frosted Pop-Tarts.

Storage & Make-Ahead

Room Temperature: Store cookies in an airtight container for up to 4 days. Keep parchment between layers to prevent sticking.
Freezer: Freeze unbaked, filled cookie dough balls for up to 2 months. Bake straight from frozen, adding 1–2 minutes to the bake time.
Baked Cookies: Freeze fully cooled cookies (without glaze) for up to 2 months. Thaw at room temperature, then glaze fresh for best results.
Make-Ahead: You can prepare the dough and filling 1–2 days ahead. Store separately in the fridge and assemble when ready to bake.

Serving Suggestions

Warm with Coffee: A freshly glazed cookie and a hot cup of coffee make a perfect afternoon treat.
Breakfast Dessert: These cookies are playful enough to serve at brunch alongside fruit and pastries.
Party Platters: Stack them on a cake stand or platter for a nostalgic dessert table centerpiece.
Ice Cream Sandwiches: Place a scoop of vanilla ice cream between two cookies for an over-the-top dessert.

FAQ

Do I have to fill the cookies?

Technically no, but the cinnamon filling is what makes these unique. Without it, they’re still delicious brown sugar cookies — just less “Pop-Tart” inspired.

Can I make the glaze ahead of time?

Yes. Store the glaze in the fridge for up to 2 days. Bring to room temperature and whisk again before using.

Can I use salted butter?

Yes. If using salted butter, reduce the added salt in the dough to ¼ teaspoon.

How do I keep the cookies soft after baking?

Store them in an airtight container with a slice of sandwich bread or a marshmallow. This helps maintain moisture.

Can I double the filling?

Yes! Just make sure to fully seal the edges of the dough so it doesn’t leak during baking.

Conclusion

Brown Sugar Pop Tart Cookies are a nostalgic nod to a childhood classic, but with a grown-up twist. The warm cinnamon filling, soft brown sugar dough, and sweet glaze combine to create a cookie that’s both familiar and totally new.

They’re surprisingly easy to make, fun to customize, and always a hit whether you’re baking for friends, family, or just yourself. One bite, and you’ll see why these have quickly become one of my most-requested cookie recipes.