Ruby Cherry Drops

Step into a world of nostalgic delight with these utterly charming and irresistibly delicious old-fashioned Cherry Wink Cookies. A true testament to classic baking, these cookies offer a delightful symphony of textures and flavors. Each bite delivers a soft, chewy interior perfectly contrasted by a crisp, crunchy coating of cornflake cereal. Inside, a rich medley of chopped pecans, sweet maraschino cherries, and tender dates creates a flavor profile that’s both festive and comforting. These aren’t just cookies; they’re a timeless treat, brimming with a little bit of everything wonderful.

Why Cherry Wink Cookies Remain a Beloved Classic

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If you’ve yet to experience the magic of Cherry Wink Cookies, prepare yourself for a truly special culinary journey. These aren’t merely cookies; they’re a celebration of texture, flavor, and a rich history that has cemented their place in the hearts of dessert lovers for decades. What makes this recipe an enduring favorite? It’s the masterful blend of ingredients that work in harmony to create an unforgettable eating experience.

At the core of their appeal is the captivating contrast: a tender, buttery interior that melts in your mouth, enveloped by a remarkably crisp and crunchy cornflake crust. This dual texture is a hallmark of the Cherry Wink, setting it apart from other traditional cookies. But the indulgence doesn’t stop there. Each cookie is generously studded with a delightful combination of chopped pecans, offering a nutty richness; sweet, vibrant maraschino cherries, adding a burst of fruity flavor and appealing color; and soft, chewy dates, contributing a unique caramel-like sweetness and satisfying chew.

The legacy of these prize-winning cookies traces back to Ruth Derousseau, who first introduced her ingenious creation to the 2nd annual Pillsbury baking contest in 1950. Her recipe quickly became a sensation, lauded for its innovative use of cornflakes and its festive presentation. To this day, Cherry Wink Cookies continue to be a star at holiday cookie exchanges, family gatherings, and celebrations, proving that some recipes are simply too good to fade away. Their ability to deliver a complex sensory experience with straightforward ingredients is a testament to their brilliance. They evoke a sense of nostalgia while satisfying a modern craving for delightful textures and balanced sweetness.

If you appreciate the unique crunch that cornflakes bring to baked goods, you might also enjoy exploring other recipes that feature this versatile cereal. Discover our no-bake cornflake cookies for a quick and easy treat, or get into the festive spirit with our charming cornflake Christmas wreaths.

Key Ingredients and Customization Tips for Perfect Cherry Winks

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Crafting the perfect batch of Cherry Wink Cookies begins with understanding the role of each ingredient and knowing how to make smart substitutions. This section provides a detailed overview of what you’ll need and how you can personalize your cookies to suit your taste.

The Cookie Dough Base: Shortening vs. Butter

• Shortening: The original recipe calls for shortening, which contributes to a tender, soft, and slightly chewier cookie with a wonderful texture. Shortening also helps the cookies maintain their shape during baking, preventing excessive spreading.
• Unsalted Butter: If you prefer the rich flavor of butter, you can absolutely substitute shortening with an equal amount of unsalted butter. Keep in mind that butter has a lower melting point than shortening and contains water, which may result in a slightly crispier cookie that spreads a little more. The flavor, however, will be undeniably rich and delicious.
• Salted Butter: Should salted butter be your only option, ensure you omit the additional salt specified in the recipe card to avoid overly salty cookies. The goal is balance!

The Star Additions: Cherries, Pecans, and Dates

• Maraschino Cherries: These vibrant red cherries are integral to the signature look and flavor of Cherry Wink Cookies. Chop them finely and, crucially, pat them thoroughly dry with paper towels before incorporating them into the dough. This step prevents excess moisture from altering the dough’s consistency and ensures the cherries distribute evenly without “bleeding” too much color into the cookies. For an extra festive touch, especially during the holidays, consider mixing red and green maraschino cherries. The contrasting colors add to the visual appeal.
• Pecans: Chopped pecans lend a buttery, earthy crunch that perfectly complements the soft cookie dough. Feel free to experiment with other nuts if pecans aren’t your favorite or readily available. Walnuts offer a similar texture and a slightly bolder flavor, while almonds can add a delicate, subtly sweet note. Always ensure nuts are fresh for the best taste.
• Dates: The inclusion of chopped dates provides a lovely chewy texture and a natural, caramel-like sweetness that deepens the cookie’s flavor profile. If dates aren’t to your liking, or you’re simply looking for an alternative, raisins or dried cranberries can be excellent substitutes. These dried fruits will still offer a pleasant chewiness and a touch of fruity sweetness, altering the flavor slightly but maintaining the spirit of the cookie.

The Signature Coating: Cornflake Cereal

• Coarsely Crushed Cornflakes: This ingredient is non-negotiable for achieving the iconic crispy, crunchy exterior of Cherry Wink Cookies. Ensure the cornflakes are crushed, but not pulverized into a fine powder. A coarse crush provides the best textural contrast. This outer coating transforms a simple cookie into a multi-sensory delight, making the “wink” truly special.

By understanding these key components and their potential variations, you can confidently prepare a batch of Cherry Wink Cookies that are not only delicious but also perfectly tailored to your preferences. The printable recipe card at the end of this post will provide all the precise measurements and instructions you need to get started.

Crafting Your Own Prize-Winning Cherry Wink Cookies: A Step-by-Step Guide

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Making these cherished Cherry Wink Cookies is a straightforward and rewarding process. Follow these detailed steps to ensure your cookies turn out perfectly, with that irresistible balance of soft chewiness and crunchy exterior.

1. Cream the Wet Ingredients: Begin by combining the granulated sugar and shortening (or unsalted butter if substituting) in a large mixing bowl. Using a hand mixer or stand mixer, cream these two ingredients together on medium speed until the mixture is light, fluffy, and pale in color. This process typically takes about 2-3 minutes and is crucial for incorporating air into the dough, which contributes to the cookies’ tender texture.

   
   

2. Incorporate Liquids and Eggs: To the creamed mixture, add the milk, vanilla extract, and eggs. Continue to beat with the mixer until all ingredients are well combined and smooth. Ensure there are no streaks of unmixed egg or liquid. Scrape down the sides of the bowl as needed to fully integrate everything.

   
   

3. Combine Dry Ingredients: In a separate, medium-sized bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Whisking ensures these dry ingredients are evenly distributed, which is important for consistent leavening throughout the cookies.

4. Combine Wet and Dry Mixtures: Gradually add the whisked dry ingredients to the wet mixture in the large bowl, mixing on low speed until just combined. Be careful not to overmix the dough, as overmixing can develop the gluten in the flour, leading to tougher cookies. Mix just until no pockets of dry flour remain.

   
   

5. Fold in the Flavorful Additions: Gently fold in the chopped pecans, chopped dates, and the prepared chopped maraschino cherries (remember to pat them dry!). Use a spatula for this step to avoid overworking the dough and to ensure the additions are evenly distributed without crushing them. The dough will look colorful and chunky.

   
   

   
   

6. Shape and Coat the Cookies: Use a 1-1/2 to 2 Tablespoon cookie scoop to form uniform dough balls. This ensures even baking. Once scooped, firmly roll each dough ball in the coarsely crushed cornflakes, ensuring all sides are thoroughly coated. The cornflakes are key to the cookie’s signature crunch! Place the coated dough balls on a lightly greased or parchment-lined baking sheet, spacing them about 2 inches apart to allow for spreading.

7. Add the Final Cherry Touch: For an extra decorative and classic touch, take the remaining whole or halved maraschino cherries and gently press a piece onto the top of each cookie dough ball before baking. This adds a beautiful visual element and signals the delightful cherry flavor within.

   
   

8. Bake to Perfection: Preheat your oven to 375°F (190°C). Bake the cookies for 10-15 minutes, or until the edges are lightly golden and the cornflake coating is crispy. The center of the cookies should still be soft. Baking times can vary depending on your oven, so keep a close eye on them.

9. Cool and Enjoy: Once baked, remove the baking sheet from the oven and allow the cookies to rest on the sheet for about 2 minutes. This brief resting period helps them set and prevents them from breaking. After 2 minutes, carefully transfer the cookies to a wire cooling rack using a spatula to cool completely. Cooling on a rack ensures air circulation, maintaining the crispness of the cornflake coating.

Frequently Asked Questions & Expert Baking Tips

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Even seasoned bakers have questions, and these expert tips will help you master your Cherry Wink Cookies, ensuring every batch is as perfect as the last.

Can I freeze Cherry Wink Cookies?

Yes, Cherry Wink Cookies are excellent candidates for freezing, whether baked or as dough. You can store baked cookies in an airtight container or a large freezer-safe zip-top bag for up to 2 months. To preserve the best texture, separate layers with parchment paper. When ready to enjoy, simply thaw them at room temperature.

For ultimate freshness, we recommend freezing the dough balls *before* adding the cornflake coating. Scoop and shape the dough balls, then place them on a baking sheet lined with parchment paper. Freeze until solid, then transfer the frozen dough balls to an airtight container or freezer bag. They can be stored for up to 2 months. When you’re ready to bake, roll the frozen dough balls in the crushed cornflakes and top with a cherry, then bake as directed, adding a few extra minutes to the baking time if needed.

Should these cookies be kept at room temperature or in the refrigerator?

Cherry Wink Cookies are best stored at room temperature. Keep them in an airtight container for 3-4 days to maintain their freshness and crisp exterior. Storing them in the refrigerator is generally not recommended as it can cause the cornflake coating to soften and the cookies to dry out.

What if my cornflake coating doesn’t stick well?

Ensuring the cornflake coating adheres properly is key to the Cherry Wink experience. Make sure your dough balls are firm enough; if the dough is too warm or sticky, the cornflakes might not stick. Chill the dough for 15-30 minutes before rolling if needed. Also, make sure the cornflakes are coarsely crushed, not too fine, to give them something to grip onto. Rolling firmly but gently will help them embed into the dough.

How can I prevent my cookies from spreading too much?

Several factors can cause cookies to spread. Ensure your shortening or butter is at the correct temperature (room temperature, but not melted). Chilling your cookie dough balls for about 15-20 minutes before rolling them in cornflakes and baking can also significantly reduce spreading. Make sure your oven is preheated to the correct temperature, as a too-cool oven can cause cookies to spread before setting. Lastly, avoid using warm baking sheets; always use cool baking sheets for each batch.

Can I make these cookies ahead of time for the holidays?

Absolutely! These cookies are perfect for holiday prep. You can bake them a few days in advance and store them at room temperature in an airtight container. Alternatively, prepare the dough, scoop into balls, and freeze as described above. This allows you to bake fresh batches whenever guests arrive or the holiday craving strikes.

Serving Suggestions for Your Cherry Wink Cookies

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Cherry Wink Cookies are versatile delights that fit perfectly into a variety of occasions. Their festive appearance and comforting flavors make them a true crowd-pleaser.

• Classic Pairing: Serve these cookies with a tall, cold glass of milk for a timeless treat. The simplicity of milk allows the complex flavors and textures of the cookie to shine.
• Holiday Cheer: For a truly decadent holiday experience, pair them with a mug of rich homemade eggnog. The creamy, spiced beverage complements the fruity and nutty notes of the cookies beautifully.
• Coffee or Tea Time: These cookies are also wonderful alongside a warm cup of coffee or your favorite tea, making them a perfect companion for a cozy afternoon break or a delightful end to a meal.
• Cookie Swaps and Exchanges: As prize-winning cookies, Cherry Winks are a guaranteed hit at any holiday cookie swap. Their unique texture and festive look will make them stand out.
• Edible Gift-Giving: Pack a batch of these beautiful cookies into decorative tins or bags tied with ribbon for a thoughtful and delicious homemade gift during the holidays or for any special occasion. They’re sure to bring a smile to anyone’s face.
• Dessert Platter: Include Cherry Winks on a festive dessert platter with other holiday favorites to offer a variety of flavors and textures to your guests.

Explore More Delicious Cookie Recipes

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If you’ve fallen in love with baking these delightful Cherry Wink Cookies, you’re likely always on the lookout for your next favorite cookie recipe. Here are a few more delicious options to inspire your baking adventures, each offering its own unique charm:

• Butter Cookies: Simple, elegant, and melt-in-your-mouth delicious, these classic butter cookies are perfect for any occasion and endlessly customizable.
• Snowball Cookies: Also known as Mexican Wedding Cakes, these delicate, nutty, and powdery cookies are a holiday staple that’s easy to love.
• Thumbprint Cookies: A beautiful and tasty cookie featuring a soft center indented with a dollop of your favorite jam or fruit preserve.
• Danish Butter Cookies: Recreate the beloved taste of those iconic blue tin cookies with this rich, buttery, and incredibly satisfying recipe.
• Orange Crinkle Cookies: Brighten up your cookie tray with these zesty, soft, and chewy cookies, bursting with fresh orange flavor and coated in powdered sugar.
• Chocolate Peanut Butter Cookies: A classic combination that’s always a hit, these rich and indulgent cookies are a dream for chocolate and peanut butter lovers.
• Reeses Pieces Cookies: Fun, colorful, and packed with peanut butter candy, these cookies are a chewy, sweet treat that’s hard to resist.

I genuinely love to bake and cook, and my greatest joy comes from sharing my kitchen experiences and cherished recipes with all of you! To make sure you never miss out on a new recipe, I offer a convenient newsletter delivered right to your inbox every time a new post goes live. Simply subscribe today and start receiving your daily dose of delicious inspiration!

The recipes on this blog are carefully tested using a conventional gas oven and gas stovetop. Please note that oven performance can vary, especially with older models, leading to inconsistent cooking and baking. We highly recommend using an inexpensive oven thermometer to verify that your oven reaches and maintains the correct temperature. If you use a toaster oven or a countertop oven, be aware that heat distribution might differ from a full-sized conventional oven, and you may need to adjust your cooking or baking times accordingly. For recipes prepared with pressure cookers, air fryers, slow cookers, or other appliances, a link to the specific models we use is typically provided within each recipe. In baking recipes where ingredient measurements are given by weight, achieving consistent results might be challenging if cups are used instead, and we cannot guarantee success with volumetric measurements.