Dainty Cherry Winks

Classic Cherry Wink Cookies: The Ultimate Vintage Recipe for Holiday Baking

Cherry Wink Cookies are more than just a sweet treat; they are a delightful journey back in time, offering a perfect blend of chewy and crunchy textures that evoke warm memories of simpler days. This treasured old-fashioned recipe features a rich, buttery cookie dough generously studded with sweet dates and crunchy pecans. Each cookie is then artfully rolled in crushed cornflakes, creating an irresistible outer crunch, and finally crowned with a vibrant maraschino cherry, transforming it into a truly iconic vintage masterpiece. Prepare to be enchanted by these charming cookies, a staple for holiday platters and a testament to enduring baking traditions.

Cherry Wink Cookies stacked on a blue serving plate.

The Sweet History of Cherry Wink Cookies

The captivating story of Cherry Wink Cookies begins in 1950, when the renowned Pillsbury company hosted its second annual baking contest, a national event that shaped American home baking for decades. It was during this prestigious competition that a remarkable recipe, submitted by Ruth Derousseau of Wisconsin, captured the judges’ hearts and taste buds, earning her the coveted winner’s title. Since that momentous year, this unique and incredibly delicious cookie recipe, officially known as “Cherry Winks,” has continuously graced cookie swaps, family gatherings, and holiday platters across the United States. Despite being over 70 years old, the recipe’s charm and deliciousness have ensured its enduring popularity, making it a beloved classic that transcends generations. Its distinctive combination of ingredients and textures cemented its place in cookie lore, proving that some recipes are truly timeless.

With their unmistakable bright red maraschino cherry gleaming atop a golden, cornflake-crusted base, these cookies possess an inherent festive quality. Their vibrant appearance makes them an absolutely perfect choice for celebrating the holidays, whether it’s Christmas, Valentine’s Day, or any special occasion that calls for a touch of cheer. Imagine a batch of these beautiful cookies gracing your holiday table, bringing smiles to guests, or perhaps carefully arranged on a plate for Santa’s annual visit. They offer a taste of nostalgia and a visual treat, making them an ideal addition to any seasonal celebration.

Are you a true cookie enthusiast, always on the hunt for your next baking adventure? If so, you’re in for a treat! In addition to these magnificent Cherry Winks, we have a selection of other irresistible cookie recipes you might love to try. Explore the rich flavors of Reese’s Peanut Butter Cookies, savor the comforting taste of Old Fashioned Iced Molasses Cookies, or indulge in the nutty goodness of Pecan Butter Cookies. Each recipe offers a unique journey for your palate!

Close-up of Cherry Wink Cookies, showing the cornflake coating and a maraschino cherry.

Essential Ingredients for Your Cherry Wink Cookie Recipe

Crafting the perfect batch of Cherry Wink Cookies requires a thoughtful selection of ingredients, each playing a vital role in achieving their distinctive flavor and texture. You will find a complete, detailed printable recipe card with exact measurements at the very bottom of this recipe post. Here’s a closer look at what you’ll need and why each component is important:

Granulated Sugar – White granulated sugar is essential here. It provides the primary sweetness and contributes to the crispness around the edges of the cookies, balancing the chewiness of the interior. Use a good quality, standard granulated sugar for consistent results.

Shortening – This recipe traditionally calls for shortening, which helps create a wonderfully tender and light cookie texture, preventing excessive spread during baking. For the best results and a healthier option, we recommend using non-hydrogenated shortening if you can find it. While butter can be substituted, shortening offers a unique tenderness that is characteristic of classic Cherry Winks.

Milk – Any variety of milk will work perfectly in this recipe. Whether you have skim, 2%, or whole milk on hand, it will contribute to the dough’s moisture and richness, helping to bring all the ingredients together seamlessly. I personally used skim milk, and the cookies turned out beautifully.

Vanilla Extract – Vanilla is a fundamental flavor enhancer in almost any cookie. For the most authentic and robust flavor, real vanilla extract is always my preference. However, if imitation vanilla is what you have in your pantry, feel free to use it; your cookies will still be delicious!

Eggs – Eggs act as a crucial binder, adding structure, moisture, and richness to the cookie dough. They also aid in leavening, contributing to the cookie’s rise and overall texture. I typically bake with large white eggs, but brown, organic, or free-range large eggs are all excellent and perfectly suitable options.

All-Purpose Flour – Standard all-purpose flour is the foundation of these Cherry Winks. It provides the necessary structure to hold all the wonderful add-ins. Always measure your flour correctly, preferably by weight or by spooning it into a measuring cup and leveling it off, to avoid a dense cookie.

Baking Powder and Baking Soda – These two leavening agents work in harmony to give the cookies their delightful lift and tender crumb. Baking powder provides initial lift, while baking soda reacts with acidic ingredients (if any, or in the dough itself) to create additional air pockets. Any brand of baking powder and baking soda will work effectively.

Salt – A small but mighty ingredient, a touch of salt is indispensable in baking. It doesn’t just add salinity; it profoundly enhances and balances the sweetness of the sugar and deepens the flavors of all the other ingredients, making each bite more satisfying.

Pecans – Pecans introduce a fantastic nutty flavor and a satisfying crunch that beautifully complements the chewy texture of the dates and cherries. I used unsalted pecans and chopped them finely. If you can find pre-chopped pecans, that will save you a step and work just as well. For an even deeper flavor, consider toasting your pecans lightly before adding them to the dough.

Dates – Sweet, sticky, and wonderfully chewy, chopped dates are a signature ingredient in Cherry Wink Cookies, contributing a rich, caramel-like sweetness and a delightful texture. Ensure your dates are properly chopped into small, manageable pieces so they distribute evenly throughout the dough and are easy to chew.

Maraschino Cherries – These vibrant red cherries are perhaps the most iconic feature of Cherry Winks, providing a burst of fruity flavor and a stunning visual appeal. You’ll need them both chopped and incorporated into the cookie batter, and as a garnish on top of each cookie. Find them canned in the canned fruit aisle of your grocery store. Crucially, after chopping the cherries for the batter, pat them thoroughly dry with paper towels to remove excess moisture. This step is vital to prevent the dough from becoming too wet and to ensure the cherries don’t bleed too much color into the cookies.

Corn Flakes Cereal – The distinctive crispy coating of crushed cornflakes is what sets Cherry Winks apart. Any brand of corn flakes cereal will work; simply make sure to crush them coarsely. This adds an incredible textural contrast to the soft interior of the cookie, transforming it from good to truly great. You can crush them by hand, in a zip-top bag with a rolling pin, or in a food processor for varying textures.

A batch of unbaked Cherry Wink Cookies, rolled in cornflakes and topped with cherries, on a baking sheet.

Step-by-Step Guide: How to Make Cherry Wink Cookies

Baking these classic Cherry Wink Cookies is a rewarding experience. Follow these detailed steps to ensure perfectly chewy, crunchy, and delightful results every time. Remember to read through the entire recipe before you begin!

Mixing sugar and shortening for Cherry Wink Cookies.

First Step: In a large mixing bowl, combine your granulated sugar and shortening. Using an electric mixer, beat these ingredients on medium speed. Continue mixing until the mixture becomes light, fluffy, and well blended. Make sure to scrape down the sides of the bowl occasionally with a rubber spatula to ensure everything is thoroughly incorporated.

Second Step: To the creamed sugar and shortening mixture, add the milk, vanilla extract, and eggs. Beat well after each addition, ensuring the ingredients are fully combined. This helps to create a smooth, emulsified base for your cookie dough.

Third Step: In a separate bowl, whisk together your dry ingredients: all-purpose flour, baking powder, baking soda, and salt. Gradually add this dry mixture to the wet ingredients in the large mixing bowl. Beat on low speed until a cohesive dough begins to form. Be careful not to overmix; overmixing can lead to tough cookies. Again, scrape down the sides of the bowl as needed to ensure even mixing.

Adding pecans, dates, and chopped cherries to the cookie dough.

Fourth Step: Now it’s time to incorporate the star additions! To the prepared cookie dough, gently stir in the chopped pecans, chopped dates, and the ⅓ cup of chopped maraschino cherries (remember to pat these dry!). Fold them in until they are evenly distributed throughout the dough. You want every bite to have a taste of these delicious mix-ins.

Close-up of cookie dough with pecans, dates, and cherries mixed in.

Fifth Step: If your dough feels a bit too sticky or soft to handle easily, cover the bowl tightly with plastic wrap and refrigerate it for about 15 minutes. This chilling period will firm up the dough, making it much easier to scoop and roll into balls, and helps prevent the cookies from spreading too much during baking.

Sixth Step: Preheat your oven to 375°F (190°C). While the oven heats, prepare your cookie sheets. Spray them lightly with cooking spray to prevent sticking, or for even easier cleanup and consistently browned bottoms, line them with parchment paper. This step is crucial for non-stick baking.

Cookie dough balls being rolled in crushed cornflakes.

Seventh Step: Take rounded teaspoonfuls of cookie dough and drop each one into your bowl of coarsely crushed cornflakes. Roll the dough ball around until it is thoroughly coated on all sides with the cornflakes. Once coated, gently shape the dough into neat balls. Place these cornflake-crusted balls approximately 2 inches apart on your prepared baking sheets, allowing room for them to spread slightly.

Maraschino cherry halves being pressed onto the cornflake-coated cookie dough balls.

Eighth Step: For that signature Cherry Wink look, take one of your maraschino cherry halves (remember these are the ones cut in half, not chopped into the dough) and lightly press it onto the very top center of each cornflake-coated cookie dough ball. This creates a beautiful visual and adds another layer of fruity flavor.

Baked Cherry Wink Cookies on a cooling rack.

Ninth Step: Bake the cookies in the preheated oven for 10 to 15 minutes. Baking times can vary depending on your oven, so keep a close eye on them. The cookies are done when their edges are lightly golden brown and the centers are just set. Avoid overbaking to maintain their chewy texture.

Tenth Step: Once baked, remove the cookie sheets from the oven and let the cookies cool on the sheets for approximately 1 minute. This brief cooling period allows them to firm up slightly. After a minute, carefully transfer the cookies to a wire rack to cool completely. Cooling on a rack ensures air circulation, preventing soggy bottoms and allowing the cornflake coating to remain crisp.

Cherry Wink Cookies on a serving platter, with some broken to show the interior.

Loved This Recipe? Pin It for Later!

If you’ve fallen in love with this classic recipe for vintage Cherry Wink Cookies and want to ensure you can easily find it again, don’t let it slip away! Make sure to save it to your favorite Pinterest recipe board before you move on. It’s the perfect way to keep this delicious piece of baking history handy for future holidays and celebrations!

Overview shot of Cherry Wink Cookies on a cooling rack and a plate.

Frequently Asked Questions About Cherry Wink Cookies

Here are some common questions and helpful answers to ensure your Cherry Wink baking experience is a complete success:

What cereal can I use instead of cornflakes? To honor the original 1950 Pillsbury Bake-Off winning recipe, Cherry Wink Cookies are traditionally coated in cornflakes, which provide their signature crunch and flavor. However, if you’re looking for an alternative or just want to experiment, Betty Crocker’s similar recipe, “Cherry Blinks,” famously used Wheaties cereal for its coating. You could also try other lightly sweetened, crisp cereals, but be aware that the flavor and texture will be slightly different from the classic.

How can I store Cherry Wink Cookies to keep them fresh? These old-fashioned cookies are delightful for days after baking! You can store them in an airtight container at room temperature on your kitchen counter for 3-4 days. To extend their freshness even longer, place them in the freezer for up to a few months. When freezing, place them in a single layer on a baking sheet to flash freeze, then transfer to a freezer-safe bag or container, separating layers with parchment paper to prevent sticking. Thaw at room temperature before serving.

Can I use butter instead of shortening in this recipe? Yes, butter can certainly be used as a substitute for shortening in Cherry Wink Cookies. Many bakers prefer the rich flavor that butter imparts. However, keep in mind that shortening contributes to a slightly chewier, more tender cookie and helps prevent excessive spreading. If you use butter, ensure it is unsalted for better control over the salt content. Margarine is generally not recommended as a 1-to-1 substitution due to its higher water content, which can significantly alter the cookie’s texture and spread.

Can I make the cookie dough ahead of time? Absolutely! This is a great time-saving tip, especially during busy holiday seasons. You can prepare the cookie dough (up to the point before rolling in cornflakes and adding the top cherry) and store it, tightly covered with plastic wrap, in the refrigerator for up to 2-3 days. When ready to bake, let the dough sit at room temperature for about 15-20 minutes to soften slightly before scooping and proceeding with the cornflake coating and cherry topping steps.

What are some serving suggestions for Cherry Wink Cookies? Cherry Winks are perfect on their own with a cup of coffee or tea, especially during the holidays. They also make a fantastic addition to any cookie platter or dessert buffet. For a special touch, serve them alongside a scoop of vanilla ice cream or a dollop of whipped cream. Their festive appearance makes them excellent for gift-giving in decorative tins or bags.

Close-up of baked Cherry Wink Cookies, showcasing their golden crust and cherry topping.

Creative Substitutions and Variations for Your Cherry Winks

While the classic Cherry Wink recipe is perfect as is, don’t hesitate to get creative with these delicious cookies. Here are some ideas to customize them to your liking, offering new flavor profiles and textures:

  • Alternative Dried Fruits: If dates aren’t your favorite or you simply don’t have any on hand, try substituting with an equal amount of chopped raisins or currants. These will still provide a wonderful chewy texture and a complementary sweetness.
  • Chocolatey Twist: For those who love a bit of chocolate in their cookies, mini chocolate chips or finely chopped chocolate pieces make a delightful addition. Fold them into the dough along with the pecans and dates for an extra layer of indulgence.
  • Tropical Flair: Add a touch of tropical sweetness by incorporating shredded coconut into the cookie dough. This will add a pleasant texture and a lovely, subtle coconut flavor that pairs beautifully with the cherries.
  • Vanilla Glaze: Elevate the visual appeal and add another layer of sweetness by drizzling the cooled cookies with a simple vanilla glaze. A mix of powdered sugar, milk, and vanilla extract creates a perfect finish.
  • Citrusy Zing: For a bright, zesty counterpoint to the sweetness, consider adding some finely grated lemon zest or orange zest to your cookie dough. This will introduce a subtle citrus note that makes the flavors pop.
  • Festive Cherry Mix: Instead of just red maraschino cherries, use a combination of red and green maraschino cherries. This variation is particularly striking and festive, making the cookies even more appealing for Christmas or other holiday celebrations.
  • Almond Essence: For a distinct flavor departure, substitute the vanilla extract with almond extract. Almond and cherry flavors are a classic pairing, and this switch will give your Cherry Winks a sophisticated, nutty aroma and taste.
  • Nut Variety: If pecans aren’t available, walnuts or even a mix of different chopped nuts can be used to provide that essential crunch and earthy flavor.

More baked Cherry Wink Cookies, close-up, highlighting the texture.

Expert Tips & Tricks for Perfect Old-Fashioned Cherry Wink Cookies

Achieving bakery-quality Cherry Wink Cookies at home is easier than you think with these simple yet effective tips:

  • Room Temperature Ingredients: Always ensure your butter (if using), shortening, and eggs are at room temperature before you begin mixing. This allows them to cream together more smoothly and evenly, resulting in a lighter, more consistent dough and a better texture in your final cookies.
  • Perfectly Crushed Cornflakes: For that ideal crunchy coating, finely but coarsely crush your cornflakes. A simple method is to place them in a zip-top plastic bag and gently crush them with the bottom of a heavy glass measuring cup or a rolling pin. Avoid turning them into a fine powder; you want distinct flakes for texture.
  • Toast Your Pecans: To deepen their flavor and add an extra layer of nutty aroma, lightly toast your chopped pecans before adding them to the dough. Spread them on a baking sheet and bake at 350°F (175°C) for 5-7 minutes, or until fragrant. Let them cool completely before incorporating.
  • Properly Dry Cherries: When chopping the maraschino cherries that go into the dough, it is absolutely crucial to pat them thoroughly dry with paper towels. Excess moisture can make your dough too wet and cause the cookies to spread more than desired, or even lead to discoloration of the dough.
  • Accurate Measuring: Baking is a science, and precise measurements are key. Use proper measuring cups and spoons, and for flour, spoon it into the cup and level it off rather than scooping directly, which can compact the flour and result in too much.
  • Uniform Cookie Size: Use a cookie scoop to ensure each dough ball is the same size. This not only makes your cookies look professional but also ensures they bake evenly, preventing some from burning while others are undercooked.
  • Don’t Overbake: Keep a close eye on your cookies during the last few minutes of baking. Cherry Winks are best when they are just set and lightly golden brown around the edges. Overbaking can lead to dry, hard cookies. They will continue to set slightly as they cool.
  • Cooling Process: Allowing the cookies to cool for a minute on the hot baking sheet helps them firm up before transferring. Then, moving them to a wire rack ensures air circulates around all sides, preventing condensation and keeping the cornflake coating crisp.
  • Making Ahead: If you’re planning for a party, the cookie dough can be made a day or two in advance and refrigerated. Just remember to bring it to a slightly warmer temperature before scooping and coating.

Close up of a bite out of a White Chocolate Cherry Cookies

Explore More Delightful Cherry Recipes to LOVE

If you’re a fan of the sweet and tangy flavor of cherries, you’re in for a treat! Beyond these classic Cherry Wink Cookies, there’s a whole world of cherry-infused desserts and baked goods to explore. Here are some other fantastic cherry recipes that we think you’ll absolutely adore:

  • White Chocolate Cherry Cookies (pictured above) – A luxurious twist on a classic, combining creamy white chocolate with vibrant cherries.
  • Cherry Cheese Bread – A delightful sweet bread perfect for breakfast or brunch, featuring a luscious cherry and cream cheese swirl.
  • Cherry Dessert – A simple yet elegant dessert that highlights the natural sweetness of cherries, ideal for any occasion.
  • Fried Ice Cream Pie – An unexpected and indulgent dessert, offering a playful combination of textures and flavors, often featuring cherries.
  • Cherry-Filled Coffee Cake – A comforting and moist coffee cake bursting with a sweet cherry filling, perfect for a morning treat.
  • Cherry Pie Jell-O Salad – A retro favorite that brings together the fun of Jell-O with the deliciousness of cherry pie.

And don’t forget to check out all the amazing Cookie Recipes shared today in our #ChristmasCookies recipe group at the bottom of this post! You’ll find a treasure trove of inspiration for your holiday baking.

SEE ALL OF MY COOKIES HERE!

A large stack of Cherry Wink Cookies on a white plate, with a decorative napkin.

If you’re yearning for a taste of pure nostalgia and a cookie that embodies the joy of old-fashioned baking, then these rich, chewy, and crunchy Cherry Wink Cookies are an absolute must-try. They are a delightful reminder of baking traditions passed down through generations. So, put on some classic Nat King Cole, brew yourself a warm cup of tea, and indulge in the simple, comforting pleasure of these timeless treats. They’re perfect for creating new memories or reliving cherished old ones with every delicious bite.

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Cherry wink cookies stacked on a blue serving plate with one broken in half.

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Print Recipe

Cherry Wink Cookies

Cherry wink cookies are old-fashioned chewy and crunchy cookies that will take you back, way back to the good old days. Rich cookie dough stuffed with dates and pecans is then rolled in crushed cornflakes and topped with a maraschino cherry to make a true vintage cookie.
Prep Time10 minutes
Cook Time15 minutes
Additional Time15 minutes
Total Time40 minutes
Course: Cookies
Cuisine: American
Keyword: cherry blink cookies, cherry cookies, cherry wink cookies, Christmas, cookie recipes, cornflakes, dates, holiday baking, Maraschino cherries, pecans, Valentines Day, vintage cookies
Servings: 3 dozen
Calories: 139kcal
Author: Michaela Kenkel

Equipment

  • Kitchenaid Stand Mixer
  • KitchenAid Hand Mixer
  • Wilton Stainless Steel Cookie Scoop
  • 13×18 Half Sheet Pan
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Ingredients

  • 1 cup sugar
  • ¾ cup shortening
  • 2 Tablespoons milk
  • 1 teaspoon vanilla
  • 2 eggs
  • 2 ¼ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ½ teaspoon salt
  • 1 cup chopped pecans
  • 1 cup chopped dates
  • cup chopped maraschino cherries patted dry with paper towels
  • 1 ½ cups coarsely crushed corn flakes cereal
  • 30 maraschino cherries cut in half

Instructions

  • In a large bowl, beat sugar and shortening with an electric mixer on medium speed, scraping the bowl occasionally, until well blended.
  • Beat in milk, vanilla, and eggs.
  • On low speed, beat in flour, baking powder, baking soda, and salt, scraping the bowl occasionally, until dough forms.
  • Stir in pecans, dates, and 1/3 cup of chopped cherries. If necessary, cover with plastic wrap and refrigerate for 15 minutes for easier handling.
  • Pre-heat oven to 375°F. Spray cookie sheets with cooking spray.
  • Drop dough by rounded teaspoonfuls into cereal; coat thoroughly. Shape into balls. Place 2 inches apart on cookie sheets.
  • Lightly press the maraschino cherry quarter on top of each ball.
  • Bake for 10 to 15 minutes or until light golden brown. Cool for 1 minute; remove from cookie sheets to cooling racks.

Nutrition

Serving: 1 | Calories: 139kcal | Carbohydrates: 18g | Protein: 2g | Fat: 7g | Saturated Fat: 2g | Polyunsaturated Fat: 4g | Cholesterol: 13mg | Sodium: 74mg | Fiber: 1g | Sugar: 11g

Welcome to #ChristmasCookies Week! That time of year when we soften the butter, fire up the oven, and make cookie trays for family, friends, and neighbors. This year more than 20 top-notch bloggers are sharing their very favorite creations for all to make and enjoy. Join us for a week’s worth of Christmas cookie deliciousness.

  • Almond Paste Squares by Shockingly Delicious
  • Cherry Vanilla Pinwheels by Jolene’s Recipe Journal
  • Cherry Wink Cookies by An Affair from the Heart
  • Chewy Frosted Christmas Blondie Cookie Bar by Red Cottage Chronicles
  • Chocolate Blossom Cookies by Palatable Pastime
  • Chocolate Mint-Filled Cookies by Karen’s Kitchen Stories
  • Cranberry Orange Shortbread Cookies by Art of Natural Living
  • Cranberry White Chocolate Chip Cookies by Hostess At Heart
  • Eggnog Snickerdoodle Cookies by Best Cookie Recipes
  • Elf Style Chocolate Chip Peppermint Cookies by Cheese Curd in Paradise
  • Gingerdoodles by Magical Ingredients
  • Gingerbread Magic Cookie Bars by Family Around the Table
  • Gingerbread Oatmeal Cookies by A Kitchen Hoor’s Adventures
  • Gluten-Free Chocolate Spritz by Frugal & Fit
  • Grinch Cookie Recipe by Kathryn’s Kitchen Blog
  • Nut-Free Snowball Cookies by Faith, Hope, Love, and Luck Survive Despite a Whiskered Accomplice
  • Peanut Butter Snickerdoodles by Christmas Tree Lane
  • Raspberry Pistachio Thumbprints by Sweet Beginnings
  • Rosewater Pistachio Snowball Cookies by The Spiffy Cookie
  • Sourdough Ginger Cookies by That Recipe
  • Toffee Bars by A Day in the Life on the Farm
  • Toffee Chocolate Chip Cookies by Hezzi-D’s Books and Cooks
  • Whipped Shortbread Cookies by Blogghetti