Festive Cupcake Creations: How to Bake and Decorate Pilgrim Hats
These charming cupcakes are adorned with mini pilgrim hats, each one a tiny edible masterpiece. Imagine sinking your teeth into moist, flavorful cake topped with creamy frosting, crowned by a meticulously crafted chocolate hat – a nod to the traditions of yesteryears. Whether you’re hosting a festive feast or simply want to add a touch of nostalgia to your dessert table, our Pilgrim Hat Cupcakes are a delightful tribute to the spirit of gratitude and togetherness.
More Thanksgiving Treats:
Turkey Moon Pies: Gobble Up Fun: Making Turkey Moon Pies and Other Sweet Turkey-Themed Treats! Are you ready to gobble up some creative and delicious turkey-themed sweet treats? Prepare to embark on a delightful culinary adventure that not only satisfies your sweet tooth but also brings out your inner artist.
Chocolatey Turkey Pretzel Bite: Need another fun AND super easy turkey treat to make with your kids? These Turkey Pretzel Bites require no baking at all! Just grab a few ingredients and 10 minutes and you’ll have a fun treat. These are perfect for parties, playdates or just a fun snack!
Turkey Graham Crackers: This super adorable Turkey Graham Crackers snack will be the star of the show! Kids and adults alike will most certainly want to give them a try. The best part is they use only 4 ingredients and are oh-so-easy to make!
Turkey Cupcakes: Do your kids love to help you make cupcakes? These Turkey Cupcakes are the perfect treat to make with your kids. They are easy and fun and the kids can get creative and make their Turkeys look as goofy as they want.
Pilgrim Hat Cupcakes Ingredients:
For the cupcakes:
- 3 c sugar
- 3 c flour
- 1 ½ c cocoa powder
- 1 T. baking powder
- 1 t. Salt
- 4 eggs
- ½ c oil
- 2 t. Vanilla
- 1 ½ c milk
- 1 ½ c water
For the frosting:
- 1 c unsalted butter, softened
- 1 t salt
- 1 t vanilla
- 4 c powdered sugar
- Yellow and orange food coloring
To decorate:
- 1 family-size package of stripe cookies
- 36 snack-size Reese’s cups
- 36 Reese’s pieces candies – only the orange and yellow
Pilgrim Hat Cupcakes Directions:
Preheat the oven to 350 degrees and prep your muffin pan(s) with liners. Set aside.
For the cupcakes:
In the bowl of a stand mixer, combine the dry ingredients – sugar, flour, cocoa powder, baking powder, and salt. Whisk to combine.
Add the liquid ingredients, including eggs, oil, milk, water, and vanilla, to the mixing bowl. Mix on low speed for one minute and then bump up the speed to medium and mix for an additional two minutes. Stop the mixer, scrape down the sides and mix again.
Measure the cake batter to each cupcake liner until about ⅔ full. Bake in the preheated oven for approximately 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:
In the bowl of a stand mixer, combine the softened butter, vanilla, salt and about half of the powdered sugar.

Mix on low speed until combined. 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. Mix 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.
Assembly:
Prepare your workspace with a strip of parchment paper. Lay out the stripe cookies so that the stripes are down and the solid chocolate is facing up. Place a dollop of frosting on the top of Reese’s cup and then invert it so that the frosting adheres 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. We like to alternate colors so that the Reese’s pieces are different than the frosting around the hat. You may mix and match however you see fit.
With the remaining frosting, pipe a flat rosette or mound on each cupcake.
Top with your assembled hats and gently press to secure.
FAQs:
- We highly recommend piping bags for these cupcakes. We also used a large star tip, but a round tip would work as well.
- Gel food colors that you can find at hobby stores or online are more concentrated than the liquid kind you find at most grocery stores. We recommend the gel variety to get vibrant colors!
Storage: Cupcakes can be stored in an airtight container for up to 3 days in the fridge or 3 months in the freezer.
Print the Recipe:
How to Make Pilgrim Hat Cupcakes
Whether you're hosting a festive feast or simply want to add a touch of nostalgia to your dessert table, our Pilgrim Hat Decorated Cupcakes are a delightful tribute to the spirit of gratitude and togetherness.
Ingredients
- For the cupcakes:
- 3 c sugar
- 3 c flour
- 1 ½ c cocoa powder
- 1 T. baking powder
- 1 t. Salt
- 4 eggs
- ½ c oil
- 2 t. Vanilla
- 1 ½ c milk
- 1 ½ c water
- For the frosting:
- 1 c unsalted butter, softened
- 1 t salt
- 1 t vanilla
- 4 c powdered sugar
- Yellow and orange food coloring
- To decorate:
- 1 family size package stripe cookies
- 36 snack size Reese’s cups
- 36 Reese’s pieces candies - only the orange and yellow
Instructions
- Preheat the oven to 350 degrees and prep your muffin pan(s) with liners. Set aside.
- For the cupcakes: In the bowl of a stand mixer, combine the dry ingredients - sugar, flour, cocoa powder, baking powder, and salt. Whisk to combine.
- To the mixing bowl add the liquid ingredients: eggs, oil, milk, water and vanilla. Mix on low speed for one minute and then bump up the speed to medium and mix for an additional two minutes. Stop the mixer, scrape down the sides and mix again.
- Measure about the cake batter to each cupcake liner until about ⅔ full. Bake in the preheated oven for approximately 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: In the bowl of a stand mixer, combine the softened butter, vanilla, salt and about half of the powdered sugar. Mix on low speed until combined. 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. Mix 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.
- Assembly: Prepare your workspace with a strip of parchment paper. Lay out the stripe cookies so that the stripes are down and the solid chocolate is facing up. Place a dollop of frosting on the top of a Reese’s cup and then invert it so that the frosting adheres 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. We like to alternate colors so that the Reese’s pieces are different than the frosting around the hat. You may mix and match however you see fit.
- With the remaining frosting, pipe a flat rosette or mound on each cupcake. Top with your assembled hats and gently press to secure.



















