Pilgrim Hat Cookies are the delightful treat that brings a touch of Thanksgiving charm to any gathering. These whimsical cookies, resembling the iconic hats worn by the Pilgrims, are not only fun to make but also deliciously satisfying. With their chocolatey tops and sweet, creamy filling, Pilgrim Hat Cookies have become a beloved favorite during the fall season. They evoke a sense of nostalgia, reminding us of cozy family gatherings, gratitude, and the warmth of tradition. Whether you’re looking to impress at a potluck or simply want to create a festive dessert at home, these cookies are sure to capture hearts and taste buds alike.
What Is Pilgrim Hat Cookies
Pilgrim Hat Cookies are an inventive dessert that combines the sweetness of chocolate with a crunchy cookie base. Typically made with round cookies as the foundation, they are topped with a chocolate kiss to mimic the famous Pilgrim hat. The contrast of textures between the soft chocolate and the crisp cookie creates a delightful bite. While similar to other cookie creations, such as the classic chocolate-covered treats, Pilgrim Hat Cookies stand out due to their festive presentation and seasonal appeal, making them perfect for Thanksgiving and fall celebrations.
Why You’ll Fall in Love with This Recipe
- Easy to prepare: With simple ingredients and straightforward steps, even novice bakers can whip these up.
- Family-friendly: Kids love to help assemble these fun cookies, making it a perfect family activity.
- Visually appealing: Their unique shape and festive look make them a hit at any gathering.
- Deliciously sweet: The combination of flavors is sure to satisfy any sweet tooth.
How Does It Taste?
The flavor profile of Pilgrim Hat Cookies is a delightful balance of sweet and rich. The cookie base offers a satisfying crunch, while the chocolate kiss on top melts in your mouth with every bite. The creamy filling, often made with peanut butter or frosting, adds an additional layer of sweetness that complements the chocolate perfectly. This cookie is a celebration of flavors—sweet, creamy, and just a hint of nostalgia that will transport you back to cozy holiday moments.
Health & Ingredient Benefits
Key ingredients in Pilgrim Hat Cookies include:
- Chocolate kisses: A source of antioxidants, they can also boost your mood!
- Peanut butter: High in protein and healthy fats, it provides a satisfying richness.
- Cookies: While they treat your sweet cravings, many cookie recipes can incorporate whole grains for added fiber.
- Decorative candies: Fun and colorful, they can add a touch of joy to your treat without too many calories.
With these healthful ingredients, you can indulge in the festive spirit of Pilgrim Hat Cookies while enjoying a delightful treat that brings everyone together.
Ingredients You’ll Need
- 1 cup all-purpose flour – This forms the base of the cookie, providing structure and a chewy texture.
- 1/2 teaspoon baking powder – This helps the cookies rise and achieve a fluffy consistency.
- 1/4 teaspoon salt – Enhances the flavors of the cookie, balancing the sweetness.
- 1/2 cup unsalted butter, softened – Adds richness and moisture to the dough.
- 1/2 cup granulated sugar – Sweetens the cookies and contributes to their chewy texture.
- 1/2 cup brown sugar – Adds moisture and a hint of caramel flavor, deepening the overall taste.
- 1 large egg – Acts as a binder, helping to hold the ingredients together.
- 1 teaspoon vanilla extract – Provides a warm, sweet flavor that complements the other ingredients.
- 1 cup chocolate candy melts (black) – Used to create the “brim” of the pilgrim hat.
- 1 cup mini peanut butter cups – These will serve as the “hat” part of the cookies.
- Yellow icing or candy – For adding the decorative buckle on the hats.
Tools You’ll Need
- Mixing bowl – For combining the cookie ingredients.
- Electric mixer – To cream the butter and sugars together effectively.
- Baking sheet – Where the cookies will be placed for baking.
- Parchment paper – To line the baking sheet for easy removal of cookies.
- Microwave-safe bowl – For melting the chocolate candy melts.
- Spatula – For spreading the melted chocolate on cookies.
- Piping bag or small zip-top bag – To pipe icing for decoration.
Optional Substitutions & Additions
- Dairy-free butter – Substitute regular butter with dairy-free alternatives for a vegan version.
- Gluten-free flour – Use a 1:1 gluten-free baking blend instead of all-purpose flour.
- Chocolate chips – Swap chocolate candy melts with dark or milk chocolate chips for the brim.
- Nut butters – Instead of peanut butter cups, use mini chocolate cups filled with almond or cashew butter for a different flavor.
How to Make Pilgrim Hat Cookies
Step 1: Prepare the Oven and Baking Sheet
Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to ensure easy cookie removal once they are baked.
Step 2: Combine Dry Ingredients
In a medium bowl, whisk together the flour, baking powder, and salt. This helps to evenly distribute the leavening agent and salt throughout the flour.
Step 3: Cream Butter and Sugars
In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar together using an electric mixer on medium speed until the mixture is light and fluffy, about 2-3 minutes. You’ll know it’s ready when it has a pale color and a creamy texture.
Step 4: Add Egg and Vanilla
Add the egg and vanilla extract to the butter-sugar mixture, beating until well combined. The mixture should be smooth and homogenous.
Step 5: Incorporate Dry Ingredients
Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed just until combined. Be careful not to overmix; you want a soft dough.
Step 6: Shape the Cookies
Using a tablespoon, scoop the dough onto the prepared baking sheet, spacing them about 2 inches apart. Flatten each scoop slightly to form a disk shape.
Step 7: Bake the Cookies
Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden. The centers may look slightly underbaked, but they will continue to firm up as they cool.
Step 8: Prepare the Chocolate Brim
While the cookies cool, melt the chocolate candy melts in a microwave-safe bowl in 30-second intervals, stirring in between until smooth. Once melted, dip the top of each cookie into the chocolate, allowing the excess to drip off.
Step 9: Add the Peanut Butter Cups
Press a mini peanut butter cup into the center of the chocolate-dipped cookie, creating the “hat” effect.
Step 10: Decorate with Icing
Using a piping bag or a small zip-top bag with a corner snipped off, pipe yellow icing onto the front of each peanut butter cup to create a decorative buckle.
What to Serve With
These delightful Pilgrim Hat Cookies pair wonderfully with a hot cup of apple cider or a warm mug of spiced tea. They also make a great addition to Thanksgiving dessert platters alongside pumpkin pie or pecan pie for a festive touch.
Tips for Success
- Ensure your butter is softened to room temperature for easy creaming with the sugars.
- Don’t skip the chilling step; it helps the cookies maintain their shape while baking.
- Use a cookie scoop for uniform cookie sizes, ensuring even baking.
- Experiment with different chocolate colors for a fun twist on the traditional Pilgrim hat.
Common Mistakes to Avoid
- Overmixing the dough can lead to tough cookies; mix just until combined.
- Not letting the cookies cool on the baking sheet for a few minutes can cause them to break apart when transferring to a cooling rack.
- Skipping the parchment paper may result in cookies sticking to the baking sheet.
How to Store & Reheat
Storing
Store your Pilgrim Hat Cookies in an airtight container at room temperature for up to five days. For longer storage, consider freezing them in a single layer before transferring to a freezer-safe container, where they can last for up to three months.
Reheating
To enjoy your cookies warm again, microwave them for about 10-15 seconds. This will soften them while preserving the chocolate texture.
Frequently Asked Questions
- Can I make these cookies ahead of time? Yes! You can bake the cookies a few days in advance and store them in an airtight container until you’re ready to serve.
- What if I don’t have chocolate candy melts? You can substitute with chocolate chips; just melt them slowly to avoid burning.
- Can I use other types of candy? Absolutely! Feel free to explore different types of chocolate cups or other candies for a unique take on the Pilgrim hat.
Nutritional Info
Each Pilgrim Hat Cookie is approximately 120 calories, with 6g of fat, 15g of carbohydrates, and 2g of protein. Keep in mind that these values can vary based on specific ingredient brands and portion sizes.

Final Thoughts
If you’re looking for a delightful treat that captures the spirit of Thanksgiving, then look no further than Pilgrim Hat Cookies! These adorable cookies not only bring a festive flair to your holiday table but also provide a fun and interactive baking experience for the whole family. With their rich chocolate and sweet frosting, Pilgrim Hat Cookies are sure to be a hit with both kids and adults alike. Plus, they make for a wonderful festive gift or a charming addition to your dessert spread. So gather your loved ones, roll up your sleeves, and get ready to create some sweet memories together with these irresistible Pilgrim Hat Cookies. Trust me, you won’t regret it!

Pilgrim Hat Cookies
This cute idea is perfect for your Thanksgiving table this year. The little bites look just like pilgrim hats and everyone is going to want to eat at least one.
Ingredients You’ll Need
- 1 Cup white chocolate chips
- ½ Cup peanut butter
- 24 mini peanut butter cups (Reese’s dark chocolate)
- 24 cookies (Keebler fudge striped)
- Mini M&Ms (red, yellow and orange)
Instructions
-
Step 1
Line a large chopping board or baking sheet with parchment paper. -
Step 2
Melt the white chocolate chips with the peanut butter in the microwave until smooth. -
Step 3
Transfer the mixture into a piping bag and let it cool for 5 minutes before using. -
Step 4
Place a fudge striped cookie on the prepared surface, stripe side down. -
Step 5
Pipe the white chocolate mixture into the middle of the cookie. -
Step 6
Add a miniature peanut butter cup on top upside down and press down. -
Step 7
Add an M&M onto the band to make a buckle. -
Step 8
Repeat until all are made and let set completely before serving.
Important Information
Nutrition Facts
Per serving: ~350 calories. Based on a 2000 calorie diet.
Allergy Information
Always check labels for specific allergen information.



