There is something unmistakably magical about High Hat Chocolate Cherry Cream Cupcakes. Just saying the name out loud feels like an invitation to indulge in a sweet little celebration. These whimsical cupcakes remind me of summer fairs and cozy winter afternoons alike, their playful peaks coated in rich chocolate, hiding a soft, cherry-flavored surprise inside.

The tradition of “high hat” desserts traces back to nostalgic soda fountains and ice cream parlors of the 1940s, where towering swirls of frosting were dipped in chocolate to create a crisp shell. Bringing that vintage magic into the kitchen today, these cupcakes are a beautiful blend of old-fashioned charm and modern indulgence. Every bite carries the essence of sweet cherries wrapped in luscious cream, cushioned by a tender chocolate base—a treat cherished by generations and a must-have at every festive gathering.

If you have a love for all things rich, creamy, and delightfully surprising, High Hat Chocolate Cherry Cream Cupcakes deserve a special spot in your baking repertoire.

Why You’ll Love This Recipe

• A playful, nostalgic dessert that’s as fun to eat as it is to make.
• Perfect for holidays, birthdays, or any day that needs a little extra sweetness.
• A luscious combination of moist chocolate cake, cherry cream filling, and crisp chocolate shell.

INGREDIENTS YOU’LL NEED

For the Cupcakes:

• 1 1/4 cups all-purpose flour
• 1/2 teaspoon baking soda
• 1/2 teaspoon baking powder
• 1/2 teaspoon salt
• 1/2 cup unsweetened cocoa powder
• 3/4 cup granulated sugar
• 1/2 cup light brown sugar
• 1/2 cup vegetable oil
• 2 large eggs
• 2 teaspoons vanilla extract
• 1/2 cup buttermilk
• 1/2 cup hot water

For the Cherry Cream Frosting:

• 1/2 cup unsalted butter, room temperature
• 1/2 cup vegetable shortening
• 2 cups powdered sugar
• 2 tablespoons cherry juice (from maraschino cherries)
• 1 teaspoon vanilla extract

For the Chocolate Coating:

• 2 cups semi-sweet chocolate chips
• 2 tablespoons coconut oil

HOW TO MAKE High Hat Chocolate Cherry Cream Cupcakes

Step-by-Step Instructions

Step 1: Make the Cupcakes

Preheat your oven to 350°F and line a cupcake pan with paper liners. In a large bowl, whisk together the flour, baking soda, baking powder, salt, and cocoa powder. In another bowl, blend the sugars with the oil, eggs, and vanilla until smooth. Gradually add the dry ingredients, alternating with the buttermilk and hot water, stirring gently until the batter is smooth.

Pour the batter into the liners, filling them about two-thirds full. Bake for 18-20 minutes, or until a toothpick inserted in the center comes out clean. Let the cupcakes cool completely before frosting.

Step 2: Make the Cherry Cream Frosting

In a mixing bowl, beat the butter and shortening until light and fluffy. Slowly add the powdered sugar, one cup at a time. Beat in the cherry juice and vanilla extract. The result should be a creamy, slightly pink frosting that holds its shape well.

Step 3: Frost the Cupcakes

Transfer the frosting to a piping bag fitted with a large round tip. Pipe tall swirls of frosting onto each cupcake, creating that classic “high hat” shape.

Step 4: Prepare the Chocolate Coating

In a microwave-safe bowl, melt the chocolate chips and coconut oil together in 30-second increments, stirring between each until smooth and glossy.

Step 5: Dip the Cupcakes

Holding each cupcake by the base, gently dip the frosted top into the melted chocolate, letting any excess drip off. Place the cupcakes upright and let the chocolate shell harden before serving.

Every time I dip these high hats into the silky chocolate, I feel like a kid again, eagerly waiting for the shell to set so I can take that first, crunchy, creamy bite.

Helpful Tips

• Chill the frosted cupcakes in the refrigerator before dipping. This keeps the frosting firm and prevents it from melting in the warm chocolate.
• If the chocolate coating is too thick for dipping, add a tiny bit more coconut oil to thin it out.
• Use high-quality cherry juice for the most vibrant flavor in the cream.
• Make sure your cupcakes are completely cool before frosting to avoid slipping or melting.

Details

• Prep Time: 30 minutes
• Cook Time: 20 minutes
• Total Time: 50 minutes
• Yield: 12 cupcakes
• Category: Dessert
• Method: Baking
• Cuisine: American
• Diet: Vegetarian

Notes

You can customize the frosting color by adding a tiny drop of red food coloring if you want a deeper cherry pink hue.

Nutritional Information

(Approximate per cupcake)

• Calories: 430
• Fat: 26g
• Carbohydrates: 48g
• Sugar: 35g
• Protein: 3g
• Fiber: 2g

Frequently Asked Questions

Can I make these cupcakes in advance?
Yes, you can bake and frost the cupcakes a day ahead. Dip them in chocolate just before serving for the freshest look.

Can I use another fruit flavor?
Absolutely! Raspberry juice or strawberry juice would work beautifully too.

How do I make sure the chocolate shell is smooth?
Ensure your frosting is chilled and your chocolate is fluid enough. Patience and a steady hand help too.

Storage Instructions

Store the High Hat Chocolate Cherry Cream Cupcakes in an airtight container in the refrigerator for up to 3 days. Allow them to come to room temperature before serving for the best texture and flavor.

Related Recipes

If you liked this recipe, you’ll definitely enjoy these other creamy delights:

• Buttery Raspberry Crumble Cookies
• Chocolate Chip Cookie Brownies
• Lemon Blueberry
• Toasted Coconut Mini Pavlovas with Coconut Custard

Conclusion

High Hat Chocolate Cherry Cream Cupcakes are a true joy to bake and an even bigger joy to share. They bring together the playful whimsy of retro dessert traditions with the luxurious flavor combinations of today’s best kitchens. Whether you are making them for a special event or simply because you feel like celebrating life’s little moments, these cupcakes will never fail to impress.

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