Looking to bake something festive, fun, and totally irresistible for Thanksgiving? These Pilgrim Hat Cupcakes are your ticket to instant Thanksgiving cheer. Picture this: soft, chocolate cupcakes swirled with orange and yellow frosting, each topped with a tiny, edible hat made from striped cookies, Reese’s cups, and Reese’s Pieces.
Beyond their adorable look, what makes these cupcakes shine is their simplicity. You can mix the batter in one bowl, whip up a fluffy frosting in minutes, and have the little hats ready before you know it. The colors pop, the flavors balance perfectly, and the presentation feels straight out of a bakery display.
Whether it’s a classroom party, a Thanksgiving dessert table, or just a cozy fall afternoon in the kitchen, these Pilgrim cupcakes are proof that festive baking doesn’t have to be complicated to look amazing.
Ingredients for Thanksgiving Cupcakes
For the cupcakes:
- 3 cups sugar
- 3 cups flour
- 1 ½ cups cocoa powder
- 1 tbsp baking powder
- 1 tsp salt
- 4 eggs
- ½ cup avocado oil
- 2 tsp vanilla
- 1 ½ cup milk
- 1 ½ cup water
For the frosting:
- 1 cup unsalted butter, softened
- 1 tsp salt
- 1 tsp vanilla
- 4 cups powdered sugar
- yellow and orange food coloring
To decorate:
- 1 family-size package of striped cookies
- 36 snack-size Reese’s cups
- 36 Reese’s Pieces candies – only the orange and yellow
Step-by-Step Instructions with Pictures
For the cupcakes:
Preheat the oven to 350°F and line your muffin pan(s) with cupcake liners.
In the bowl of a stand mixer, combine the dry ingredients – sugar, flour, cocoa powder, baking powder, and salt. Whisk to combine.
Add the eggs, oil, milk, water, and vanilla to the bowl. Mix on low for 1 minute, then on medium for 2 minutes. Scrape the sides and mix again.
Carefully pour the batter into each cupcake liner until about ⅔ full.
Bake for 14–16 minutes or until a toothpick comes out clean. Let the cupcakes cool completely before decorating.
For the frosting:
In a stand mixer bowl, beat the softened butter, vanilla, salt, and half of the powdered sugar.
Add in the remaining powdered sugar and mix on low speed until combined.
Bump up the speed to medium and mix for an additional two minutes until the frosting is smooth and fluffy-looking.
Divide the frosting between two medium-sized bowls. Tint one yellow and the other orange.
Make sure to mix it well.
Prepare two frosting bags with a large star tip (if you only have one tip, just rinse and reuse). Transfer ¾ of the orange and yellow frosting to their piping bag fitted with the tip. Transfer the remaining ¼ of the frosting to small piping bags and then cut a small hole in the end.
Line your workspace with parchment paper. Place the striped cookies stripe-side down, with the solid chocolate side facing up.
Place a dollop of frosting on the top of a Reese’s cup and then invert it so that the frosting adheres to the cup to the stripe cookie in the center.
Using your small bags of frosting, create a ring around the Reese’s cup and then a small dollop to adhere the Reese’s pieces to the cup.
Alternate colors so the Reese’s pieces stand out from the frosting around the hat.
With the remaining frosting, pipe a flat rosette or mound on the top of your cupcake.
Top the frosting with the assembled hats. Gently press to secure.
Serve the pilgrim hat cupcakes immediately or store them in the fridge until ready to enjoy.
Tips for Perfect Pilgrim Cupcakes
- Use Gel Colors: They give bright, rich frosting hues that won’t fade over time.
- Use Proper Cooling Time: Let cupcakes cool completely so the frosting stays firm and picture-perfect.
- Use Color Contrast: Alternate orange frosting with yellow Reese’s Pieces (and vice versa) for a playful, eye-catching look.
- Use Creativity: Decorating these cupcakes is a fun family activity—perfect for kids to join in on the holiday fun.
Serving Ideas
- Thanksgiving Dessert Table: Arrange the cupcakes on a pretty platter with small pumpkins or leaves for a festive touch.
- Kids’ Table Treat: Fun and colorful, these cupcakes are perfect for keeping kids happy before the big meal.
- Hostess Gift: Pack a few in a box and tie them with ribbon for a sweet, homemade gift.
- Friendsgiving Dessert: Pair them with other fall favorites like pie or cider for a cozy celebration.
- Shareable Snack: Bring a batch to work or school for an easy Thanksgiving treat everyone will love.
Recipe Variations to Try
- Chocolate Lovers’ Twist: Add mini chocolate chips to the batter or frosting for extra sweetness.
- Pumpkin Flavor: Mix a little pumpkin puree and spice into the batter to give these cupcakes a seasonal twist.
- Mini Version: Make bite-sized cupcakes for easy snacking or party trays.
Storage Tips
Store cupcakes in an airtight container for up to 3 days in the fridge. They can also be frozen (unfrosted) for up to 3 months—just thaw and decorate when ready to serve.
One Last Thing
These Thanksgiving cupcakes are more than just dessert—they’re a festive centerpiece that brings smiles to the table. The mix of chocolate, peanut butter, and creamy frosting is irresistible.
And those little hats?! Simply charming! Whether you’re baking for a feast, a school event, or a quiet weekend treat, these Pilgrim cupcakes are sure to become a Thanksgiving favorite.
More Thankgiving Desserts to Try
The Cutest Thanksgiving Pilgrim Hat Cupcakes for Your Dessert Table
Ingredients
For the cupcakes:
- 3 cups sugar
- 3 cups flour
- 1 1/2 cup cocoa powder
- 1 tbsp baking powder
- 1 tsp salt
- 4 eggs
- 1/2 cup oil
- 2 tsp vanilla
- 1 1/2 cup milk
- 1 1/2 cup water
For the frosting:
- 1 cup unsalted butter, softened
- 1 tsp salt
- 1 tsp vanilla
- 4 cups powdered sugar
- Yellow and orange food coloring
To decorate:
- 1 family-size package of striped cookies
- 36 snack-size Reese’s cups
- 36 Reese’s Pieces candies – only the orange and yellow
Instructions
For the cupcakes:
- Preheat the oven to 350°F and line your muffin pan(s) with cupcake liners.
- In the bowl of a stand mixer, combine the dry ingredients – sugar, flour, cocoa powder, baking powder, and salt. Whisk to combine.3 cups sugar, 3 cups flour, 1 1/2 cup cocoa powder, 1 tbsp baking powder, 1 tsp salt
- Add the eggs, oil, milk, water, and vanilla to the bowl. Mix on low for 1 minute, then on medium for 2 minutes. Scrape the sides and mix again.4 eggs, 1/2 cup oil, 1 1/2 cup milk, 1 1/2 cup water, 2 tsp vanilla
- Carefully pour the batter into each cupcake liner until about ⅔ full.
- Bake for 14–16 minutes or until a toothpick comes out clean. Let the cupcakes cool completely before decorating.
For the frosting:
- In a stand mixer bowl, beat the softened butter, vanilla, salt, and half of the powdered sugar.1 cup unsalted butter, softened, 1 tsp salt, 1 tsp vanilla, 4 cups powdered sugar
- Add in the remaining powdered sugar and mix on low speed until combined.
- Bump up the speed to medium and mix for an additional two minutes until the frosting is smooth and fluffy-looking.
- Divide the frosting between two medium-sized bowls. Tint one yellow and the other orange.Yellow and orange food coloring
- Make sure to mix it well.
- Prepare two frosting bags with a large star tip (if you only have one tip, just rinse and reuse). Transfer ¾ of the orange and yellow frosting to their piping bag fitted with the tip. Transfer the remaining ¼ of the frosting to small piping bags and then cut a small hole in the end.
- Line your workspace with parchment paper. Place the striped cookies stripe-side down, with the solid chocolate side facing up.1 family-size package of striped cookies
- Place a dollop of frosting on the top of a Reese’s cup and then invert it so that the frosting adheres to the cup to the stripe cookie in the center.36 snack-size Reese’s cups
- Using your small bags of frosting, create a ring around the Reese’s cup and then a small dollop to adhere the Reese’s pieces to the cup.
- Alternate colors so the Reese’s pieces stand out from the frosting around the hat. Others can mix and match however they prefer.
- With the remaining frosting, pipe a flat rosette or mound on the top of your cupcake.
- Top the assembled hats. Gently press to secure.36 Reese’s Pieces candies – only the orange and yellow
- Serve the pilgrim hat cupcakes immediately or store them in the fridge until ready to enjoy.
Notes
-
- Use Gel Colors: They give bright, rich frosting hues that won’t fade over time.
-
- Use Proper Cooling Time: Let cupcakes cool completely so the frosting stays firm and picture-perfect.
-
- Use Color Contrast: Alternate orange frosting with yellow Reese’s Pieces (and vice versa) for a playful, eye-catching look.
-
- Use Creativity: Decorating these cupcakes is a fun family activity—perfect for kids to join in on the holiday fun.
Nutrition
Tamara Tsaturyan is the owner and writer of Thriving In Parenting, a website focused on providing simple tips for busy parents — easy and healthy recipes, home decor and organization ideas and all things P A R E N T I N G.
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