Pilgrim Hat Cupcakes For Thanksgiving
These pilgrim hat cupcakes for Thanksgiving bring a touch of days gone by to our meal. The little candies sure do make these easy cupcakes!
For this fall dessert idea, I’ll use a chocolate cupcakes, however, feel free to browse all of my cupcakes for the perfect one.

RELATED READING: Yummy Cookie Dough Cupcakes are a Crowd Pleaser!
What You'll Find On This Page
Easy Pilgrim Hat Cupcakes
Here at Ruffles and Rain Boots, Thanksgiving is one of the holidays most of the family gets to gather. And of course, we have an extensive array of dessert options.
If you’re new here, I absolutely love coming up with easy cupcake recipes. These pilgrim hat cupcakes are going to be a great addition to the recipe box.
If you need time to gather your ingredients for this recipe bookmark this page so it’s easy to find when you are ready to make this pilgrim hat cupcakes recipe for Thanksgiving.

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Why These Cupcakes Are Perfect For Thanksgiving
The kids can help make the pilgrim hats while you bake and/or frost the cupcakes. They will have a blast.
Older children can bake and frost the cupcakes themselves. How proud would they be to have their own addition to the dessert table?
This recipe is from scratch, offering the nostalgia of when your mom and grandmother made cupcakes for you. If you need extra time in the kitchen to make your other dishes, use a boxed cake mix. We won’t tell!

RELATED READING: Need a Delicious Fall Snack Mix? Here You Go
Tips For Making Pilgrim Hat Cupcakes
- Pipe a single rosette onto the cupcake. Apply gentle pressure when capping your cake.
- When making the frosting, use room temperature butter. If the butter is chilled, it will not whip into the smooth and creamy texture.
- When we are using frosting, we prefer a reusable piping bag. They are easy to clean, save you money, and save the environment. You can also buy a pack of disposable bags or use a zip top bag and cut off the corner.
- If you have dense cupcakes, it can be from overmixing, opening the oven door too often, or because the oven temperature is off. We use an oven thermometer to be sure we are baking at the correct temperature and ONLY MIX until combined to avoid stretching the gluten.

Ingredients To Make Pilgrim Hat Cupcakes
Below are the ingredients we used to create our Thanksgiving Day cupcakes. Check your pantry and fridge to see what you have on hand before you head to the store. For information on the best piping bags to use for frosting, read the tips section above.
- Sugar
- Flour
- Cocoa powder
- Baking powder
- Salt
- Eggs
- Oil
- Vanilla
- Milk
- Water

How To Make This Fall Cupcake Idea
Each step for this recipe is detailed below so it’s easy to follow. Keep this page open while you are creating your holiday dessert. If you would rather have a printable recipe, scroll down and select the print button.

Preheat the oven to 350 degrees and prep your muffin pan(s) with 36 liners. Set aside. In the bowl of an electric hand or stand mixer, combine the sugar, flour, cocoa powder, baking powder, and salt. Whisk to combine.

Add in the eggs, oil, milk, water and vanilla. Mix on low speed for one minute and then increase the speed to medium and mix for an additional minute. If needed, stop the mixer, scrape down the sides, and mix again.

Add the cupcake batter to each cupcake liner until about ⅔ full. Bake for 14-16 minutes or until a toothpick inserted in the center of a cupcake comes out clean. Allow to cool completely before decorating.
Ingredients For The Buttercream Frosting And Pilgrim Hats
- Unsalted butter, softened
- Salt
- Vanilla
- Powdered sugar
- Yellow and orange food coloring
- Fudge stripe cookies
- Snack-size Reese’s Cups
- Orange Reese’s Pieces Candy
- Yellow Reese’s Pieces Candy
- Piping bags

How To Make Buttercream Frosting And Pilgrim Hats

In the bowl of an electric hand or stand mixer, combine the softened butter, vanilla, salt, and half of the powdered sugar. Mix on low speed until combined.

Add in the remaining powdered sugar and mix on low speed until combined. Increase the speed to medium and mix for an additional two minutes or until the frosting is smooth and forms small peaks.

Divide the frosting between two medium-sized bowls. Tint one yellow and the other orange.

Mix in the food coloring until the desired color is reached. Prepare two frosting bags with a large star tip. Transfer 3/4 of the orange and the yellow frosting to their individual piping bags fitted with the tip. Add the remaining frosting to individual piping bags or Ziplock bag.

Prepare your workspace with a strip of parchment paper or a cutting board. Lay out the fudge stripe cookies with the stripe side down.

Place a dollop of frosting on the top of one Reese’s cup and then turn it upside down so that the frosting adheres to the cup to the center of the cookie.

Using one of the smaller bags of frosting, create a ring around a Reese’s cup and then a small dollop to adhere the Reese’s pieces to the cup, making a button for the hat.
Repeat with half of the hats. Create the remaining hats with the other color of frosting and Reese’s Pieces.

With the remaining frosting, pipe a flat rosette or mound on each cupcake with half of the orange and then the remaining hat with the yellow. Top with your assembled hats and gently press to secure. Arrange on a dessert plate and serve.
Notes For Making Pilgrim Hat Cupcakes
- If you don’t have any Reese’s Pieces on hand, a M&M candy will work for the “button” of the hat.
- You don’t need much frosting to keep the Reese’s Cup in place as the top of the hat.
- Make the cupcakes the day before. The kids can frost the cupcakes and make the hats while you are finishing up the meal.
More Cupcakes You May Like
- Snickers Cupcakes Recipe: Snickers candy bars are a treat and just like them, these cupcakes go great with a tall, cold glass of milk.
- Yummy Bananas Foster Cupcakes Recipe: Add a dramatic effect for your guests with the flambé action of these cupcakes.
- Devil’s Food Cupcakes for Halloween: These cupcakes are sinfully delicious.
- Snickerdoodle Cupcake Recipe: Fan of those soft and fluffy Snickerdoodle cookies? You are going to love these cupcakes.
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Pilgrim Hat Cupcakes for Thanksgiving
Bring a spirit of gratitude and togetherness to your Thanksgiving table with these cute and easy pilgrim hat cupcakes. These buttercream frosted cupcakes are topped with a simple-to-make pilgrim hat.
Ingredients
Ingredients For The Cupcakes
- 3 cups sugar
- 3 cups flour
- 1 ½ cups cocoa powder
- 1 tablespoon baking powder
- 1 teaspoon Salt
- 4 eggs
- ½ cup oil
- 2 teaspoons Vanilla
- 1 ½ cups milk
- 1 ½ cups water
Ingredients For The Frosting And Pilgrim Hats
- 1 cup unsalted butter, softened
- 1 teaspoon salt
- 1 teaspoon vanilla
- 4 cups powdered sugar
- Yellow and orange food coloring
- Family size package of fudge stripe cookies
- 36 snack size Reese’s Cups
- 18 orange Reese’s Pieces Candy
- 18 yellow Reese’s Pieces Candy
Instructions
For The Cupcakes:
- Preheat the oven to 350 degrees and prep your muffin pan(s) with 36 liners. Set aside. In the bowl of an electric hand or stand mixer, combine the sugar, flour,
cocoa powder, baking powder, and salt. Whisk to combine. - Add in the eggs, oil, milk, water and vanilla. Mix on low speed for one minute and then increase the speed to medium and mix for an additional minute. If needed, stop the mixer, scrape down the sides, and mix again.
- Add the cupcake batter to each cupcake liner until about ⅔ full. Bake for 14-16 minutes or until a toothpick inserted in the center of a cupcake comes out clean. Allow to cool completely before decorating.
For The Frosting And Pilgrim Hats
- In the bowl of an electric hand or stand mixer, combine the softened butter,
vanilla, salt, and half of the powdered sugar. Mix on low speed until combined. - Add in the remaining powdered sugar and mix on low speed until combined. Increase the speed to medium and mix for an additional two minutes or until the frosting is smooth and forms small peaks.
- Divide the frosting between two medium-sized bowls. Tint one yellow and the other orange.
- Mix in the food coloring until the desired color is reached. Prepare two frosting bags with a large star tip. Transfer 3/4 of the orange and yellow frosting to their individual piping bags fitted with the tip. Transfer the remaining frosting to their individual piping bags.
- .Prepare your workspace with a strip of parchment paper or cutting board. Lay out the fudge stripe cookies with the stripe side down. Place a dollop of frosting on the top of a Reese’s cup and then turn it upside down so that the frosting adheres to the cup in the center of the cookie.
- Using one of the smaller bags of frosting, cut a small hole in the tip and create a ring around the Reese’s cup and then use a small dollop to adhere the Reese’s pieces to the cup, making a button for the hat.
- With the remaining frosting, pipe a flat rosette or mound on each cupcake. Top with your assembled hats and gently press to secure.
Nutrition Information:
Yield:
36Serving Size:
1Amount Per Serving: Calories: 428Total Fat: 18gSaturated Fat: 7gTrans Fat: 0gUnsaturated Fat: 10gCholesterol: 37mgSodium: 269mgCarbohydrates: 64gFiber: 4gSugar: 49gProtein: 6g
All nutrition information is estimated. For accuracy, please calculate your exact brands and ingredients if accuracy is desired.

Meet the Creator
Hi there, I’m Sarah Nenni-Daher. I’m a crafty gal and always have at least 14 projects going at once. I am a crafter, designer, DIYer, and pattern maker. I share my creations here and in the Ruffles and Rain Boots® Shop.
Here at Ruffles and Rain Boots®, you’ll find DIY gnomes, crafts, gifts, cupcakes, laser crafts, and so much more. I love sharing video tutorials over on YouTube and chatting with other crafters in my Facebook groups. We’d love to have you!