Name: Pumpkin Sandwich Cookies with Cinnamon Sugar and Chocolate Filling
Prep time: 30 min
Cook time: 15 min
Total time: 45 min
Cuisine: American
Ingredients: 1 1/2 cups (3 sticks) salted butter, softened; 1 1/4 cups light brown sugar, packed; 1 tbsp pure vanilla extract; 2 large eggs, at room temperature; 4 1/2 cups all-purpose flour; 1 tsp baking soda; 1 tsp cinnamon; 1/2 tsp ground ginger; 1/4 tsp nutmeg; 1/2 tsp salt; 12 oz milk chocolate, melted; 2 tbsp salted butter (for brushing); 3 tbsp cinnamon sugar (for topping)

Pumpkin Sandwich Cookies with Cinnamon Sugar and Chocolate Filling

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These Pumpkin Sandwich Cookies are a playful and delicious fall treat, perfect for Halloween parties, cozy autumn afternoons, or just when I want to bake something seasonal and sweet. With spiced cookie dough, a layer of melted milk chocolate, and a buttery cinnamon sugar topping, these cookies deliver the perfect balance of warmth, richness, and fun.

Why You’ll Love This Recipe

I love how these cookies bring together everything I crave during fall—cinnamon, nutmeg, ginger, and chocolate. The texture is soft but sturdy enough to sandwich a creamy layer of milk chocolate. The cute pumpkin shapes make them perfect for entertaining or gifting, and brushing them with browned butter and cinnamon sugar adds an irresistible finishing touch. Pumpkin Sandwich Cookies with Cinnamon Sugar and Chocolate Filling

Ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

3 sticks (1 1/2 cups) salted butter, softened
1 1/4 cups light brown sugar, packed
1 tablespoon pure vanilla extract
2 eggs, at room temperature
4 1/2 cups all-purpose flour
1 teaspoon baking soda
1 teaspoon cinnamon
1/2 teaspoon ginger
1/4 teaspoon nutmeg
1/2 teaspoon salt
12 ounces milk chocolate, melted

Cinnamon Sugar Coating

2 tablespoons salted butter
3 tablespoons cinnamon sugar

Directions

I start by creaming the butter, brown sugar, and vanilla together in a large bowl until light and fluffy—about 3–5 minutes.
I add the eggs one at a time, mixing well after each addition. Then I stir in the flour, baking soda, cinnamon, ginger, nutmeg, and salt until a dough forms.
On a well-floured surface, I divide the dough in half and shape each into a disk. I roll each disk out to 1/4-inch thickness and use a pumpkin cookie cutter to cut out shapes.
I place the cut-out cookies on a parchment-lined baking sheet. For half of them, I cut eyes and a mouth using a paring knife. Then I freeze the tray for 15–20 minutes until the cookies are firm. I re-roll any scraps and repeat.
I preheat the oven to 350°F and bake the cookies for 8–12 minutes until lightly golden but still soft. After 5 minutes of cooling on the baking sheet, I transfer them to a wire rack.
I melt the 2 tablespoons of butter in a small pot until lightly browned and fragrant, then brush it over the tops of the cookies with faces. I immediately sprinkle with cinnamon sugar.
To assemble, I spread melted milk chocolate on the bottom halves (those without faces) and press the top cookies gently over them. I serve them right away or let the chocolate set.

Servings and timing

This recipe makes 30 sandwich cookies. Prep takes about 30 minutes, with a 15-minute bake time and total time of around 45 minutes.

Variations

I sometimes swap the milk chocolate for dark or white chocolate for a flavor twist.
For a more intense fall flavor, I increase the cinnamon or add a dash of clove.
If I want crunch, I add finely chopped nuts like pecans or walnuts into the dough.
I’ve also used maple extract in place of vanilla for a deeper, richer taste.

storage/reheating

I store these cookies in an airtight container at room temperature for up to 3 days. To extend their life, I refrigerate them for up to a week. If I want the chocolate filling slightly gooey again, I warm the cookie for about 5–10 seconds in the microwave.

FAQs

Can I make the dough ahead of time?

Yes, I often make the dough a day ahead and store it wrapped in the fridge. It’s even easier to work with once chilled.

What if I don’t have a pumpkin-shaped cutter?

No problem—I just cut 3-inch circles and use a paring knife to make the faces by hand.

Can I freeze these cookies?

Yes, I freeze the assembled cookies in a single layer, then store them in a container with parchment between layers for up to 1 month.

What type of chocolate works best?

I like using good-quality milk chocolate bars melted down, but chocolate chips work in a pinch too.

How do I keep the cookies from spreading?

I always chill the cut cookies before baking—freezing them for 15–20 minutes helps them hold their shape perfectly in the oven.

Conclusion

These Pumpkin Sandwich Cookies are the kind of treat that makes fall baking magical. The spiced cookie base, silky chocolate center, and cinnamon sugar top make them both visually charming and delicious. Whether I’m baking for a crowd or just indulging myself, they never last long on the plate.