Blushing Cherry Bites

Step back in time and rediscover a beloved classic with our irresistible Cherry Winks recipe! These vintage-inspired cookies offer a delightful journey for your taste buds, perfectly balancing a wonderfully crunchy exterior, generously studded with cornflake crumbs, and a super soft, tender interior. Each bite is a symphony of flavors and textures, loaded with the sweet-tartness of maraschino cherries, the rich, earthy notes of pecans, and the chewy sweetness of finely chopped dates. More than just a dessert, Cherry Winks are a bite of edible nostalgia, bringing warmth and comfort to any gathering, especially during the festive holiday season. Get ready to bake a batch that will surely become a cherished part of your family’s traditions.

Plate piled with cherry winks cookies with light pink cookie showing through cornflake crumb exterior with a piece of a bright red maraschino cherry in the middle.

These delightful cookies earned their charming name, “Cherry Winks,” because a quartered maraschino cherry nestled in the center seems to give a playful little “wink” from atop its golden, crumbly bed. The soft, chewy, and subtly fruity cookie dough is meticulously coated with crushed cornflake crumbs, creating an addictively crispy layer that contrasts beautifully with the moist, cake-like interior. This unique combination of textures, from the initial satisfying crunch to the melt-in-your-mouth softness, is what makes Cherry Winks truly stand out.

The cookies themselves are thoughtfully designed to be lightly sweet, allowing the natural sugars and vibrant flavors of the dates and cherries to truly shine. This delicate sweetness is perfectly complemented by the robust, nutty undertones of pecans and the wholesome, familiar crunch of cornflakes. It’s a harmonious blend that harks back to simpler times and embodies the essence of classic American baking. This distinct flavor profile, coupled with the charming visual appeal, firmly places Cherry Winks among those treasured vintage recipes that evoke a sense of home and tradition. They’re not just cookies; they’re a timeless culinary experience that continues to captivate generations.

Close plate of old fashioned cherry winks cookies with bits of cornflakes on the outside and a cherry in the center.
Half of a cherry winks cookie showing the bits of dates, cherries, and pecans inside.

These delightful treats would make an exceptional addition to your holiday baking repertoire, bringing a touch of nostalgic charm and festive cheer to your Christmas cookie platters. Imagine the smiles they’ll bring, reminding everyone of cherished family memories and the simple joys of homemade goodness. We firmly believe it’s high time these charming old-fashioned treats experienced a well-deserved resurgence in popularity, becoming a staple in modern kitchens once again. Their unique character and comforting taste are simply too good to be confined to history books.

The Enduring Appeal of Cherry Winks: A Recipe Rooted in History

The original Cherry Winks recipe holds a special place in American culinary history, having first graced the pages of a Pillsbury baking contest entry way back in the 1950s. This esteemed competition, known for unearthing timeless recipes that captured the hearts and palates of the nation, propelled Cherry Winks into the spotlight. Since their initial debut, these iconic cookies have been featured in numerous Pillsbury cookbooks, solidifying their status as a beloved classic.

This rich heritage means there’s a strong likelihood that your own mother, grandmother, or even great-grandmother may have lovingly prepared a batch or two of these cookies at some point. For many families, Cherry Winks are far more than just a recipe; they are a cherished tradition, meticulously baked and enjoyed every holiday season. They represent a connection to the past, a taste of shared memories, and the enduring comfort of homemade treats passed down through generations.

What truly sets Cherry Winks apart is the masterful balance of its components. The cookie dough itself is intentionally designed to be only lightly sweet. This deliberate approach allows the vibrant, natural sweetness and distinct flavors of the chopped dates and maraschino cherries to truly shine through, becoming the stars of the show rather than being overshadowed by excessive sugar. This delicate sweetness ensures each cookie is a nuanced and satisfying experience.

Making the cherry winks dough with a mixer bowl with the wet ingredients, a mixing bowl with the dry ingredients, a bowl of chopped pecans, and a plate with drained maraschino cherries and dates.
Scooping dough into a bowl of crushed cornflakes to coat the exterior with a bowl of slivered maraschino cherries nearby and a baking tray with finished cookies in the background, ready to go in the oven.

One of the delightful conveniences of this recipe is that there’s no need to chill the dough before baking. In fact, a slightly sticky dough is preferred, as it ensures that the crushed cornflake crumbs adhere perfectly, creating that signature crunchy coating. This means you can go from mixing bowl to oven in no time, making them a fantastic choice for last-minute baking cravings or unexpected guests.

The crowning touch, and indeed the namesake, of these cookies is the small sliver of maraschino cherry placed delicately on top of each dough ball. Gently pressing it down slightly before placing the cookies in the oven helps it to set securely, ensuring that iconic “wink” remains perfectly visible after baking. This simple step not only adds to the aesthetic appeal but also guarantees a burst of cherry flavor with every cookie.

The finished appearance of Cherry Winks is truly uniquely vintage. There’s an undeniable charm in the light pink hue of the cookie peeking through the golden, irregularly textured cornflake crumbs, all capped off with that bright red cherry. It’s a visual that instantly transports you to grandma’s cozy kitchen, filled with the aroma of freshly baked treats and heartwarming memories. This distinctive look, combined with their exceptional taste, makes them an instant favorite and a conversation starter on any dessert table.

Cookie sheet lined with a silicone mat topped with freshly baked cherry wink cookies expanded slightly so the pink dough shows through the cornflake exterior.
Freshly baked cherry winks on a wire cooling rack.

While these old-fashioned Cherry Wink cookies are most frequently associated with Christmastime, and often featured prominently on holiday dessert platters, there’s absolutely no reason to limit their enjoyment to just one season. Their delightful flavors and textures make them a versatile treat that can be enjoyed year-round. Imagine them as a fun, colorful addition to your Easter brunch, a delightful surprise for a spring picnic, or simply as a comforting “just because” treat on any ordinary day. Their timeless appeal ensures they’re always a welcome indulgence.

So, whether you’ve been savoring the sweet taste of Cherry Winks your entire life, carrying on a beloved family tradition, or if you’re discovering these charming cookies for the very first time, this classic old-fashioned recipe is unequivocally worth adding to your baking repertoire. They possess a unique charm and irresistible flavor that are sure to earn them a special and permanent place among your own cherished traditions and favorite homemade treats. Don’t miss out on the joy of baking and sharing these delightful vintage gems!

Essential Tips and Tricks for Perfect Cherry Winks

Achieving the perfect batch of Cherry Winks is easier than you think with a few key considerations. Here are some essential tips and tricks to ensure your cookies turn out beautifully soft on the inside and perfectly crisp on the outside every single time:

  • Mind the Dough Consistency: One of the most crucial pieces of advice for any cookie dough, and especially for Cherry Winks, is to avoid overworking the dough. Once you’ve added all the ingredients, mix them just enough until they are barely combined and form a uniform dough. Overmixing develops the gluten in the flour, which can lead to tough, dense cookies instead of the desired tender, cakey texture. A light hand will yield a much more delicate crumb.
  • Prepare Your Cherries Properly: Maraschino cherries, while delicious, come packed in a sugary syrup. Before chopping and incorporating them into your dough, it’s vital to drain them thoroughly and pat them dry with paper towels. Excess moisture can alter the dough’s consistency, making it too wet, and could also affect the texture of your baked cookies. This step ensures the perfect balance of moisture and flavor.
  • The Art of the Cornflake Coating: For that signature crunchy exterior, ensure your cornflakes are crushed to the right consistency – not too powdery, but fine enough to adhere easily. You can achieve this by placing them in a Ziploc bag and crushing them with a rolling pin, or pulsing them briefly in a food processor. When rolling the dough balls, gently press them into the crushed cornflakes to ensure an even and generous coating, which will create that wonderful crispy contrast.
  • Precision in Baking: Don’t fall into the trap of overbaking these delicate cookies. Cherry Winks are designed to be soft and almost cakey in the middle, and baking them for too long will result in a dry, crumbly texture. Keep a close eye on them; remove them from the oven as soon as the edges appear lightly golden and the centers look just set. If anything, it’s better to slightly underbake them than to overbake. They will continue to firm up slightly as they cool on the baking sheet and then on a wire rack.
  • Oven Temperature Matters: Ensure your oven is preheated to the correct temperature (375°F or 190°C) before placing the cookies inside. An accurately heated oven is critical for even baking and proper spread. Consider using an oven thermometer to verify your oven’s internal temperature, as many can run hotter or colder than their display indicates.
Hand holding a cherry wink cookie with a plate of more cookies in the background.
Hand holding half of a cherry wink cookie showing the bits of cherry, dates, and pecans inside the light pink cookie and the cornflake bits on the outside.

Storing Your Baked Cherry Winks

Proper storage is key to maintaining the delightful texture and fresh taste of your homemade Cherry Winks. Here’s how to ensure they remain delicious for as long as possible:

  • Room Temperature Storage: Once completely cooled, Cherry Winks can be stored in an airtight container at room temperature for up to one week. To prevent them from drying out, consider placing a slice of fresh bread in the container; the cookies will absorb moisture from the bread, keeping them soft and fresh. Separate layers with parchment paper if stacking to prevent sticking.
  • Freezer Storage for Longer Enjoyment: For extended freshness, Cherry Winks freeze exceptionally well. Arrange completely cooled cookies in a single layer on a baking sheet and flash freeze them for about an hour until firm. Then, transfer the frozen cookies to a freezer-safe airtight container or heavy-duty freezer bag, separating layers with parchment paper. They can be stored in the freezer for up to two to three months without significant loss of quality.
  • Thawing Frozen Cookies: When you’re ready to enjoy your frozen Cherry Winks, simply remove them from the freezer and let them thaw at room temperature. They typically take about 30 minutes to an hour to thaw completely, depending on their size and ambient temperature. Avoid microwaving them, as this can alter their texture.
  • Perfect for Make-Ahead Baking: Their excellent shelf life and freezer-friendliness make Cherry Winks an ideal cookie for make-ahead baking, especially during busy holiday seasons. Prepare them weeks in advance, freeze, and then simply thaw and serve when needed, reducing stress and ensuring you always have a delicious homemade treat on hand.
Plate piled with cherry winks cookies with light pink cookie showing through cornflake crumb exterior with a piece of a bright red maraschino cherry in the middle.

5 from 2 ratings

Classic Cherry Winks Recipe

Author: Carlee
Servings: 48 Cookies
This classic cherry winks recipe will bring a touch of nostalgia to your dessert plate. They have a crunchy exterior with bits of cornflakes and a super soft cookie interior that is loaded with cherries, pecans, and dates.
Print
Pin
Rate
Prep: 15 minutes
Cook: 12 minutes
Total: 27 minutes

Ingredients 

  • 2⅓ cups all purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • 10 Tablespoons unsalted butter softened
  • 1 cup granulated sugar
  • 2 Tablespoons milk
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 10 ounces maraschino cherries divided
  • 14 dates pitted and finely chopped
  • ¾ cup toasted pecans chopped
  • cups crushed cornflakes

Instructions 

  • Preheat oven to 375℉ (190°C) and line cookie sheets with either parchment paper or silicone mats for easy release.
  • In a medium bowl, whisk together the all-purpose flour, baking powder, and salt until well combined. Set aside.
    2⅓ cups all purpose flour, 2 teaspoons baking powder, ½ teaspoon salt
  • In a large mixing bowl, or the bowl of a stand mixer fitted with the paddle attachment, cream together the softened unsalted butter and granulated sugar until the mixture is light, fluffy, and pale in color.
    10 Tablespoons unsalted butter, 1 cup granulated sugar
  • Gradually beat in the eggs one at a time, mixing well after each addition. Then, stir in the milk and vanilla extract until just combined, scraping down the sides of the bowl as needed.
    2 Tablespoons milk, 2 large eggs, 1 teaspoon vanilla extract
  • Slowly add the dry ingredients to the wet ingredients, mixing on low speed until they are just mostly incorporated. Be careful not to overmix.
  • Drain the maraschino cherries thoroughly and pat them very dry with paper towels. Quarter approximately 12 of the cherries and set these aside for decoration. Finely chop the remaining cherries.
    10 ounces maraschino cherries
  • Gently fold the chopped cherries, finely chopped dates, and chopped toasted pecans into the dough. Mix until these flavorful additions are evenly distributed throughout the cookie dough.
    14 dates, ¾ cup toasted pecans
  • Prepare a small bowl with the crushed cornflake crumbs. Using a tablespoon or a small cookie scoop, scoop out portions of dough and roll each into a ball. Roll each dough ball thoroughly in the cornflake crumbs until fully coated. Place the coated cookie dough balls onto the prepared baking sheet, ensuring about 1 inch of space between each cookie. Finally, take one of the reserved quartered cherry pieces and gently press it into the center of each dough ball, creating that signature “wink.”
    1½ cups crushed cornflakes
  • Bake for approximately 12 minutes, or until the edges are lightly golden and the centers appear just set. Avoid overbaking to keep the cookies soft and moist. Remove the baking sheet from the oven and let the cookies cool on the sheet for a few minutes before carefully transferring them to a wire rack to cool completely.
  • Once entirely cooled, store your Cherry Winks in an airtight container at room temperature for up to one week. For longer preservation, they can be frozen for up to two to three months.

Email Me The Link

I’ll email this post to you, so you can easily find it later. Plus you’ll get new recipes from me every week!

Show Nutrition InformationHide Nutrition Information

Nutrition Information

Serving: 1Cookie | Calories: 104kcal | Carbohydrates: 19g | Protein: 2g | Fat: 3g | Saturated Fat: 2g | Polyunsaturated Fat: 0.2g | Monounsaturated Fat: 1g | Trans Fat: 0.1g | Cholesterol: 13mg | Sodium: 99mg | Potassium: 38mg | Fiber: 1g | Sugar: 9g | Vitamin A: 219IU | Vitamin C: 2mg | Calcium: 18mg | Iron: 3mg


“Cooking With Carlee” is not a dietitian or nutritionist, and any nutritional information shared is an estimate. If calorie count and other nutritional values are important to you, we recommend running the ingredients through whichever online nutritional calculator you prefer. Calories and other nutritional values can vary quite a bit depending on which brands were used.

Did you try this delightful recipe?

We’d love to hear your thoughts! Don’t forget to leave a rating and comment below to share your experience. For more delicious recipes and baking inspiration, be sure to follow us on Pinterest and Instagram!