Grandmas Beloved Cherry Wink Cookies

Step back in time with Grandma’s cherished recipe for Cherry Wink Cookies. These old-fashioned delights, featuring a tender, chewy interior, vibrant maraschino cherries, crunchy pecans, and a distinctive cornflake crust, are a true taste of holiday nostalgia. Perfect for festive gatherings, cookie swaps, or simply a comforting treat with a warm drink, these vintage cookies bring a heartwarming charm to any occasion.

The Timeless Appeal of Cherry Wink Cookies

There’s something truly magical about a recipe passed down through generations, and these Cherry Wink Cookies are no exception. Discovered in my own grandma’s treasured recipe collection, this classic cookie embodies the warmth and tradition of homemade holiday baking. With their soft, chewy texture, generously studded with chopped dates (or cranberries), bright maraschino cherries, and crunchy pecans, each bite is a journey back to simpler times.

What sets these cookies apart is their unique coating of crushed cornflakes, providing an irresistible crunch that beautifully contrasts with the tender dough. Crowned with a quartered maraschino cherry, these cookies are said to mimic a cheerful winking eye – a charming detail that gives them their distinctive name!

This beloved recipe gained national fame when Ruth Derousseau won the coveted Pillsbury Bake-Off in 1950. Its popularity soared, even appearing on Kellogg’s cornflake boxes, solidifying its place in American baking history. Recreating these cookies isn’t just baking; it’s participating in a legacy of joy and deliciousness that has spanned decades.

Whether you’re planning a grand Christmas cookie exchange, assembling festive dessert trays, or simply seeking a comforting companion for a glass of cold milk, a hot cup of coffee, or rich cocoa, these Cherry Winks are the perfect choice. Their vibrant color and delightful flavor make them an instant favorite during the holiday season and beyond.

What Makes Cherry Winks So Special?

Beyond their charming name and rich history, Cherry Wink Cookies stand out for a combination of delightful characteristics:

• Unique Texture Profile: They offer a remarkable contrast between the soft, melt-in-your-mouth dough and the crispy, golden cornflake crust. This dual texture keeps every bite exciting.
• Festive Flavors: The sweet, slightly tangy maraschino cherries paired with earthy, buttery pecans create a harmonious flavor profile that is quintessentially holiday. The vanilla-infused dough provides a comforting base.
• Eye-Catching Appearance: The bright red cherry halves perched on top, surrounded by the golden cornflakes, make these cookies visually appealing and instantly recognizable. They add a pop of color to any dessert spread.
• Versatility: While traditionally a Christmas cookie, their universal appeal makes them suitable for any special occasion. They’re also incredibly forgiving for bakers of all skill levels.
• Nostalgic Value: For many, these cookies evoke cherished memories of childhood, family gatherings, and grandmother’s kitchen, making them more than just a dessert – they’re a piece of edible history.

Essential Ingredients for Cherry Wink Cookies

Crafting these vintage beauties requires only a handful of readily available ingredients. You’ll find everything you need at your local grocery store. The full, precise measurements are detailed in the recipe card below, but here’s a closer look at what goes into these delightful cookies:

• Butter: For the best flavor and texture, use softened butter. While the original recipe sometimes called for shortening, butter imparts a richer, more nuanced taste. You can use either unsalted or salted butter; if using salted, simply reduce the added salt in the recipe slightly.
• Granulated Sugar: Standard white sugar provides the necessary sweetness and helps with the cookie’s tender crumb.
• Milk: A small amount of milk adds moisture to the dough, ensuring a soft and pliable texture. I typically use 2% milk, but whole milk or even a dairy-free alternative can work.
• Large Eggs: Eggs act as a binder, provide structure, and contribute to the richness and moisture of the cookies. Ensure they are at room temperature for better incorporation into the batter.
• Vanilla Extract: A staple in most cookie recipes, vanilla enhances all the other flavors, adding a warm, aromatic depth. Don’t skip it!
• All-Purpose Flour: The primary structural component of the cookies. Measure it correctly by spooning it into your measuring cup and leveling it off, rather than scooping directly from the bag, which can lead to too much flour.
• Baking Powder & Baking Soda: These leavening agents work together to give the cookies their gentle lift and tender texture. Ensure they are fresh for optimal results.
• Salt: A pinch of salt balances the sweetness and brings out the flavors of the other ingredients.
• Pecans: Chopped pecans add a delightful crunch and a buttery, nutty flavor that complements the cherries beautifully. Walnuts can be a suitable substitute if you prefer.
• Maraschino Cherries: These are the star! You’ll need them both chopped for mixing into the dough and sliced (quartered) for decorating the top. Make sure to drain them well and pat them dry to prevent excess moisture from affecting the dough.
• Dates (or Dried Cranberries): The original recipe features chopped dried dates, which add a sweet, caramel-like chewiness. I often opt for chopped dried cranberries for a slightly tarter twist and an extra festive red color, but raisins or other finely chopped dried fruit can also be used.
• Cornflakes: Crushed cornflakes are essential for the signature outer coating. They provide that irresistible crispy texture. You’ll want them finely crushed but still with some small pieces for texture.

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

Making these classic Cherry Wink Cookies is a straightforward and rewarding process. Follow these detailed steps for perfect results every time:

1. Prepare Your Ingredients and Equipment:

• Begin by chopping your pecans, dried dates (or cranberries), and a portion of the maraschino cherries. Set these aside.
• Slice the remaining maraschino cherries into quarters for the cookie topping. Ensure all cherries are well-drained and patted dry with paper towels to prevent introducing too much moisture into the dough.
• Crush the cornflakes: Place the cornflakes into a large gallon-sized freezer bag and crush them using a rolling pin until you have a mixture of fine crumbs and small flakes. Alternatively, you can pulse them briefly in a food processor. Pour the crushed cornflakes into a shallow bowl, ready for rolling the cookie dough.
• Preheat your oven to 375°F (190°C) and prepare your baking sheets by lightly greasing them or lining them with parchment paper or silicone mats. This prevents sticking and ensures even baking.

2. Cream Butter and Sugar:

• In a large mixing bowl, combine the softened butter and granulated sugar. Using an electric mixer (either a hand-held mixer or a stand mixer with the paddle attachment), cream them together on medium speed until the mixture is light, fluffy, and pale in color. This step incorporates air, contributing to the cookies’ tender texture.

3. Add Wet Ingredients:

• To the creamed butter and sugar, add the milk, vanilla extract, and large eggs. Beat well with the electric mixer until all ingredients are thoroughly combined and the mixture is smooth. Scrape down the sides of the bowl as needed to ensure everything is incorporated.

4. Incorporate Dry Ingredients:

• In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt.
• Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix, as this can lead to tough cookies. Stop mixing as soon as no streaks of flour remain.

5. Fold in Mix-ins:

• Using a sturdy spoon or a rubber spatula, gently fold in the chopped pecans, dates (or cranberries), and chopped maraschino cherries. Fold just enough to distribute them evenly throughout the dough, being careful not to break up the cherries too much.

6. Chill the Dough:

• Cover the mixing bowl with plastic wrap and refrigerate the cookie dough for at least 15 minutes. This chilling period is crucial as it helps firm up the dough, making it much easier to handle and shape, especially since the dough can be quite sticky. It also helps prevent the cookies from spreading too much during baking.

7. Shape and Coat the Cookies:

• Once the dough is chilled, use a tablespoon or a small cookie scoop to portion out the dough. Drop each portion directly into the bowl of crushed cornflakes.
• Roll the dough in the cornflakes, using your hands to gently shape it into a ball while ensuring it’s completely coated with the cereal. The crushed cornflakes make the sticky dough much easier to manage.
• Place the coated dough balls about 2 inches apart on your prepared baking sheets.
• Gently press a quartered maraschino cherry onto the top of each cookie. This is the “wink” that gives the cookies their charming appearance!

Baking and Cooling Your Cherry Winks

The final steps to delicious Cherry Wink Cookies involve careful baking and proper cooling:

• Baking Time: Bake the cookies in your preheated oven for 10-12 minutes. The exact time may vary slightly depending on your oven and the size of your cookies. Look for edges that are lightly golden brown and firm to the touch. The centers might still appear slightly soft, but they will set as they cool. Avoid overbaking, as this can make the cookies dry.
• Cooling: Once baked, remove the baking sheets from the oven and let the cookies cool on the sheets for a few minutes. This allows them to firm up before transferring. Then, carefully transfer the cookies to a wire rack to cool completely. Allowing them to cool fully is essential for achieving the perfect texture and for easier storage.

Storage Tips for Freshness

To enjoy your Cherry Wink Cookies at their best, proper storage is key:

• Room Temperature: Once completely cooled, store the cookies in an airtight container at room temperature. They will remain fresh, soft, and delicious for about 4-5 days. To maintain their crunch, you can place a piece of bread in the container to absorb excess moisture, though this might slightly soften the cornflake coating over time.
• Freezing for Longer Enjoyment: Cherry Wink Cookies freeze exceptionally well, allowing you to prepare them in advance or save some for later. Arrange cooled cookies in a single layer on a baking sheet and freeze until solid (about 1-2 hours). Once frozen, transfer them to a freezer-safe airtight container or heavy-duty freezer bag, layering them with parchment paper to prevent sticking. They can be frozen for up to 3 months without significant loss of flavor or texture.
• Thawing Frozen Cookies: To thaw, simply remove the desired number of cookies from the freezer and let them come to room temperature on a wire rack. This usually takes about 15-30 minutes. Avoid microwaving, as it can alter the texture.
• Dough Storage: If you want to prepare the dough ahead of time, you can chill the dough (before rolling in cornflakes) in the refrigerator for up to 2-3 days, tightly wrapped in plastic. You can also freeze the raw dough for up to a month. Thaw in the refrigerator overnight before proceeding with shaping and baking.

Expert Tips and Recipe Notes

Even though this is a straightforward recipe, a few pointers can elevate your Cherry Wink Cookies from good to absolutely perfect:

• Butter vs. Shortening: While the original 1950 Pillsbury recipe famously used shortening, many home bakers, including my grandma, prefer butter. Butter lends a richer flavor and a slightly softer chew. Feel free to experiment with either, or even a combination, to find your preferred texture.
• Chilling is Crucial: Do not skip the chilling step! Refrigerating the dough for at least 15 minutes firms it up, making it significantly less sticky and much easier to roll into balls and coat with cornflakes. Chilled dough also helps prevent the cookies from spreading excessively in the oven, ensuring they hold their charming round shape.
• Draining Cherries: Maraschino cherries are packed in syrup, which can add too much moisture to your cookie dough. Be sure to drain them thoroughly and pat them dry with paper towels before chopping and mixing them in. This prevents soggy cookies and helps maintain the dough’s consistency.
• Uniform Cookie Size: For even baking, aim for uniform cookie dough balls. A cookie scoop is an excellent tool for this, ensuring consistent size and shape across your batch.
• Rolling in Cornflakes: The dough can be a bit sticky, but the crushed cornflakes act as a natural barrier and make handling easier. As you drop the dough into the cornflakes, gently roll and press to form a ball, ensuring a good, even coating.
• Variations on Dried Fruit: My preference is often for dried cranberries instead of dates, as their tartness offers a wonderful contrast to the sweet cherries. However, raisins, finely chopped dried apricots, or a mix of various dried fruits can also be used to customize your cookies.
• Festive Cherry Colors: For an extra festive touch during the holidays, consider using a combination of red and green maraschino cherries for the topping. The vibrant colors add a playful and celebratory look to your cookie tray.
• Equipment Matters: Using parchment paper or silicone baking mats can make cleanup a breeze and helps prevent sticking. An electric mixer (stand or hand-held) is invaluable for creaming the butter and sugar, ensuring a light and airy dough.

More Holiday Cookie Inspirations

If you adore the festive spirit of Cherry Wink Cookies, you’ll love exploring other holiday treats! Be sure to try my Christmas Cornflake Wreath Cookies for another creative cornflake-based delight. For something truly whimsical and easy, consider making adorable Nutter Butter Reindeer Cookies. And if you’re a fan of classic comfort, my Best Oatmeal Chocolate Chip Cookies or Oatmeal Cranberry Walnut Cookies are always a hit.

For more delightful holiday recipes and mouth-watering cookie ideas, be sure to sign up for our weekly newsletter and follow us on social media!