Old-Fashioned Cherry Wink Cookies: The Ultimate Guide to a Prize-Winning Holiday Treat

Prepare for a delightful journey back in time with these sweet, old-fashioned Cherry Wink cookies. Each bite offers a harmonious blend of textures: a soft, wonderfully chewy interior gives way to a gloriously crisp and crunchy coating of cornflake cereal on the outside. Infused with the rich flavors of chopped pecans, juicy maraschino cherries, and tender dates, these cookies truly have a little bit of everything, making them a festive and unforgettable addition to any holiday celebration or casual gathering.

Why You’ll Love This Classic Cherry Wink Cookie Recipe

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If you’ve never had the pleasure of tasting Cherry Wink cookies, you’re in for an exceptional treat that transcends typical cookie expectations. This isn’t just any cookie recipe; it’s a piece of baking history, originally crafted by Ruth Derousseau and submitted to the prestigious 2nd annual Pillsbury baking contest in 1950. These cookies are literal prize winners, carrying with them a legacy of deliciousness that continues to make them a beloved favorite. Their unique combination of ingredients provides a complex symphony of textures, from the tender chew of the cookie base and dates, to the sweet burst of maraschino cherries, and the satisfying crunch of the cornflake coating.

Cherry Wink cookies are renowned for their ability to bring joy and festive spirit to any occasion. They are a staple at holiday cookie exchanges, family gatherings, and potlucks, often being the first to disappear from the platter. Their vibrant appearance, thanks to the colorful cherries, makes them visually appealing, while their rich, multi-layered flavor profile ensures they stand out from the crowd. The ingenious addition of a cornflake crust isn’t just for texture; it adds a subtle, toasted cereal note that complements the fruity and nutty elements perfectly.

Looking to explore more delightful cookie recipes that creatively use cornflakes? Don’t miss our fantastic no-bake cornflake cookies, perfect for quick fixes, or our festive cornflake Christmas wreaths, ideal for holiday decorating and snacking. These recipes showcase just how versatile and fun cornflakes can be in baking!

Essential Ingredients for Perfect Cherry Wink Cookies

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To embark on your Cherry Wink cookie baking adventure, you’ll need a selection of common pantry staples and a few special additions. For a comprehensive list of all measurements, ingredients, and detailed instructions, please refer to the printable recipe card available at the very end of this post.

Ingredient Spotlight: Tips for Best Results and Substitutions

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Understanding your ingredients is key to successful baking. Here’s a closer look at the components of Cherry Wink cookies and how you can adapt them to your preferences or what you have on hand:

DOUGH BASE – The original recipe for these classic cookies traditionally calls for shortening, which contributes to a uniquely tender and soft interior with less spread during baking. However, you absolutely have the option to substitute the shortening with unsalted butter if you prefer a richer flavor profile. If you decide to use butter, remember that butter has a lower melting point, which might result in a slightly flatter, crispier cookie. For those using salted butter, simply omit the additional salt specified in the recipe card to balance the flavors perfectly.

DELIGHTFUL ADDITIONS – The medley of chopped pecans, maraschino cherries, and dates is what gives Cherry Wink cookies their distinctive character and texture. For a truly festive appearance, especially around the holiday season, you can often find green maraschino cherries. Mixing both red and green cherries creates a wonderfully colorful cookie that’s perfect for gifting or a holiday dessert spread. When preparing your maraschino cherries, it’s crucial to chop them and then gently pat them dry with paper towels. This step helps remove excess moisture, preventing the cookies from becoming soggy or the color from bleeding too much into the dough.

Feel free to experiment with the nuts! While pecans offer a buttery, earthy flavor and a satisfying crunch, you can easily substitute them with any type of nuts you prefer, such as walnuts, almonds, or even hazelnuts. For those who aren’t fans of dates, don’t worry! You can leave them out entirely for a simpler cookie, or substitute them with other dried fruits like raisins, dried cranberries, or finely chopped dried apricots for a different twist on chewiness and flavor. Just ensure any dried fruit additions are also finely chopped to distribute evenly throughout the dough.

THE CRUNCHY COATING – The cornflake cereal coating is what truly sets Cherry Wink cookies apart, providing that irresistible crisp and crunchy exterior. When crushing the cornflakes, aim for a coarse crush rather than a fine powder. This ensures you get distinct pieces that contribute to the textural contrast. This step is vital for the signature “wink” effect and crunchy mouthfeel.

Ensuring all your ingredients are at room temperature (especially the shortening/butter and eggs) before you begin will help them cream together smoothly, resulting in a more uniform and tender cookie dough.

Step-by-Step: Crafting Your Cherry Wink Masterpiece

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These step-by-step photos and detailed instructions are provided to help you visualize each stage of making this classic recipe. For a complete, printer-friendly version with all precise measurements and instructions, you can Jump to Recipe at the bottom of this post.

1. **Cream the Wet Ingredients:** In a large mixing bowl, combine the granulated sugar and shortening (or butter if substituting). Using a hand mixer or stand mixer, cream these two ingredients together until the mixture is light, fluffy, and pale in color. This process incorporates air into the dough, which is essential for a tender, soft cookie texture. Make sure to scrape down the sides of the bowl periodically to ensure even mixing.
   
2. **Incorporate Liquid and Eggs:** To the creamed mixture, add the milk, vanilla extract, and eggs. Beat these ingredients together on medium speed until they are thoroughly combined and smooth. Again, take a moment to scrape down the sides of the bowl to ensure all components are fully integrated.
   
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 uniform leavening throughout your cookies.
4. **Mix Wet and Dry:** Gradually add the dry ingredients mixture to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix the dough, as overworking the flour can lead to tough cookies. Mix only until no streaks of flour remain.
   
5. **Fold in the Flavorful Additions:** Gently fold in the chopped pecans, chopped dates, and the prepared chopped maraschino cherries. Use a spatula for this step to avoid overworking the dough and to ensure the delicate ingredients are evenly distributed without being crushed.
   
6. **Form and Coat the Cookies:** Use a 1-1/2 to 2 Tablespoon cookie scoop to form uniform dough balls. This helps ensure even baking. Roll each dough ball thoroughly in the coarsely crushed cornflakes, making sure all sides are completely coated. The cornflakes will adhere best if the dough is slightly tacky. Place the coated dough balls onto a lightly greased baking sheet (or one lined with parchment paper), spacing them about 2 inches apart to allow for spread.
7. **Garnish with Cherries:** Take the remaining maraschino cherries and cut them in half or into quarters. Gently press a cherry piece onto the top of each cookie dough ball. This not only adds a beautiful visual appeal but also provides another burst of cherry flavor.
   
8. **Bake and Cool:** Preheat your oven to 375°F (190°C). Bake the cookies for 10-15 minutes, or until the edges are lightly golden and the centers are just set. Baking times can vary depending on your oven, so keep a close eye on them. Once baked, remove the cookies from the oven and allow them to rest on the baking sheet for 2 minutes. This brief resting period helps them firm up. Afterward, carefully transfer them with a spatula to a wire cooling rack to cool completely. Allowing them to cool fully on a rack ensures the cornflake coating remains crisp.

Frequently Asked Questions & Pro Tips for Cherry Wink Cookies

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Expert Tips for Cookie Perfection:

• **Room Temperature Ingredients:** Always ensure your butter/shortening and eggs are at room temperature. This allows them to emulsify properly, creating a smoother, more uniform dough and a better texture in your final cookie.
• **Don’t Overmix:** Once you add the dry ingredients, mix just until combined. Overmixing develops the gluten in the flour, resulting in tough, dry cookies.
• **Crush Cornflakes Properly:** Aim for coarsely crushed cornflakes, not a fine powder. You want distinct pieces for that iconic crunch. You can achieve this by gently crushing them in a ziptop bag with a rolling pin.
• **Pat Cherries Dry:** This step is crucial! Excess moisture from the maraschino cherries can make the dough watery and lead to color bleeding. Pat them thoroughly dry with paper towels after chopping.
• **Uniform Size:** Use a cookie scoop to ensure all your dough balls are the same size. This promotes even baking, so all your cookies are perfectly done at the same time.
• **Preheat Oven Fully:** Always preheat your oven for at least 15-20 minutes before baking to ensure it reaches and holds the correct temperature. An inexpensive oven thermometer can confirm your oven’s accuracy.
• **Cooling is Key:** Allow cookies to cool on the baking sheet for a couple of minutes before transferring to a wire rack. This helps them set and prevents them from breaking. Fully cooling on a wire rack ensures the cornflake coating stays crispy.

Delightful Serving Suggestions for Your Cherry Wink Cookies

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Cherry Wink cookies are truly versatile and perfect for a variety of serving occasions. While a tall glass of cold milk or a festive mug of homemade eggnog makes for an undeniably classic pairing, these cookies shine in many settings. They are an absolute must-have for any holiday cookie swap, guaranteed to be a crowd-pleaser and often the star of the show. Their charming appearance and delightful flavor profile also make them ideal for edible gift-giving during the holidays; arrange them in pretty tins or cellophane bags for a thoughtful homemade present. Beyond the festive season, enjoy them as an afternoon treat with a cup of freshly brewed coffee or a soothing herbal tea. They also make a wonderful addition to any dessert platter, offering a unique texture and taste among other baked goods. Whether served simply or as part of a grand spread, Cherry Wink cookies are sure to impress.

Explore More Irresistible Cookie Recipes

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• Butter Cookies
• Snowball Cookies
• Thumbprint Cookies
• Danish Butter Cookies
• Orange Crinkle Cookies
• Chocolate Peanut Butter Cookies
• Reeses Pieces Cookies

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