This recipe for Cherry Wink Cookies has been a holiday and everyday favorite in my kitchen for years. I first made a batch one late autumn afternoon when I needed something cheerful to brighten a slow, gray day. The combination of crushed cornflakes on the exterior for snap, tender cookie interior studded with dates and pecans, and the glossy maraschino cherry on top created such a contrast in textures and flavors that the cookies vanished within an hour. It felt like sharing a small celebration at the counter — friends and family kept saying these tasted like the best of old-fashioned bake-sale treats.

What makes these cookies special is the balance between crunchy and tender: the cornflake coating gives a crisp bite while the interior remains moist thanks to the shortening, eggs and a touch of half-and-half. The chopped maraschino cherries add bursts of sweet fruitiness while dates provide caramel-like chew and pecans bring toasty depth. They’re approachable enough for beginners but satisfying for experienced bakers who enjoy small technique touches like proper dough chilling, gentle mixing and careful cherry handling to avoid excess moisture.

Ingredients

• All-purpose flour: 2 cups — Use a reliable brand like King Arthur or Gold Medal. Spoon into the measuring cup and level with a knife for accurate measurement; flour creates the structure for the cookies.
• Cornflakes (crushed): 1 cup for the dough + 2 cups for coating — Toasted cornflakes add both lightness and crisp texture. Crush using a rolling pin in a bag for irregular crumbs that cling to the dough.
• Baking powder & baking soda: 1 teaspoon baking powder and 1/2 teaspoon baking soda — Work together to give a gentle lift and avoid toughness.
• Salt: 1/2 teaspoon — Enhances flavor and balances sweetness.
• Shortening: 1 cup — Offers a tender, slightly crumbly bite and helps cookies hold shape better than all-butter versions.
• Granulated sugar: 1 cup — Straightforward sweetness that also helps with spreading control.
• Eggs: 2 large, room temperature — Bring eggs to room temperature for easier emulsification and a more even texture.
• Half-and-half: 2 1/2 tablespoons — A small amount of dairy to enrich and moisten the dough.
• Vanilla extract: 1 1/4 teaspoons — Adds aromatic depth; use pure vanilla for best flavor.
• Pecans (roughly chopped): 1 cup — Toast lightly (3–5 minutes at 350°F) to awaken oils and add a nutty crunch.
• Pitted dates (roughly chopped): 1 cup — Medjool or any soft variety; chop into small pieces so they distribute evenly and don’t leach excess moisture.
• Maraschino cherries (finely chopped): 1/3 cup + 15 whole cherries quartered for topping — Pat dry thoroughly with paper towels to avoid soggy bits; the small chopped pieces go into the dough for flavor bursts.

Instructions

Preheat and prepare: Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper and set aside. This ensures even baking and easy cleanup. Position racks in the middle of the oven and allow the oven to come fully to temperature before baking. Combine dry ingredients: In a medium bowl, whisk together 2 cups flour, 1 cup crushed cornflakes, 1 teaspoon baking powder, 1/2 teaspoon baking soda and 1/2 teaspoon salt until homogeneous. Whisking distributes leaveners and avoids pockets of baking soda which can cause off flavors. Cream shortening and sugar: In a stand mixer fitted with the paddle attachment or in a bowl with a handheld mixer, beat 1 cup shortening and 1 cup granulated sugar on medium-high for 1 to 1 1/2 minutes until lightened in color and slightly fluffy. Don't overbeat; you want aeration but not warm shortening. Incorporate eggs and flavor: Reduce speed to low and add eggs one at a time, mixing until incorporated. Add 2 1/2 tablespoons half-and-half and 1 1/4 teaspoons vanilla; mix just until combined. This creates a stable emulsion for uniform texture. Mix dry into wet: With the mixer on low, slowly add the dry mixture and mix until just combined. Overmixing develops gluten and can make the cookies tough; stop when streaks of flour disappear. Fold in mix-ins: Gently fold in 1 cup chopped pecans, 1 cup chopped dates and 1/3 cup finely chopped, well-patted maraschino cherries using a spatula. Ensure even distribution while keeping the dough tender. Scoop and coat: Use a 1 tablespoon cookie scoop to portion dough. Roll each portion in the remaining 2 cups of roughly crushed cornflakes until well-coated. Shape into a ball and place on the prepared sheet about 2 inches apart to allow for slight spreading. Add cherry and bake: Press one quartered maraschino cherry into the center of each dough ball. Bake 10 to 12 minutes until the bottom edge is golden and tops are set. Rotate the pan halfway if your oven has hot spots. Remove and let rest on the sheet 2 to 3 minutes, then transfer to a rack to cool completely.

Storage Tips

Store cooled cookies in a single layer or in layers separated by parchment in an airtight container at room temperature for up to five days. For longer storage, freeze in a single layer on a tray until firm, then transfer to freezer-safe bags for up to three months. Reheat briefly in a 300°F oven for 3–5 minutes to refresh crunch, or let come to room temperature if reheating will melt the cherry garnish. Avoid refrigeration — it can cause the cornflake coating to soften.

Ingredient Substitutions

To make these without nuts, replace pecans with an equal amount of toasted sunflower or pumpkin seeds. For dairy-free needs, use a non-dairy creamer or almond milk in place of half-and-half. To make them butter-forward, substitute an equal amount of cold unsalted butter for the shortening, knowing the texture will be slightly more tender and produce a deeper butter flavor. For a lower-sugar version, reduce granulated sugar by 2 tablespoons and consider using dried unsweetened cherries mixed with a teaspoon of honey for texture.

Serving Suggestions

Serve these on a dessert platter with dark chocolate-dipped shortbread or a selection of tea sandwiches for a vintage tea party feel. They pair nicely with black tea, espresso or a lightly sweet dessert wine. For holidays, present them in a lined tin with parchment and ribbon; the bright cherry top makes them exceptionally festive. Garnish with a light dusting of powdered sugar just before serving for a snowy touch.

Cultural Background

Cookies that combine cereal coatings with fruit and nuts have roots in mid-20th century American home baking, when convenience ingredients like cornflakes and maraschino cherries became popular pantry staples. They reflect a time when bakers experimented with texture contrasts and easily available sweet preserves. The charming cherry-on-top nods to classic presentations seen in diner desserts and holiday baking alike, a small visual flourish that elevates a humble cookie into something celebratory.

Seasonal Adaptations

In summer, swap maraschino cherries for finely chopped fresh cherries tossed in a teaspoon of cornstarch to absorb juice. In autumn, replace dates with finely chopped dried figs and add a pinch of cinnamon for warmth. For winter holidays, use a splash of almond extract in place of some vanilla and fold in finely chopped candied citrus peel to brighten flavor.

Meal Prep Tips

Portion the dough with a tablespoon scoop and freeze the unbaked, coated balls in a single layer on a tray. Once firm, transfer to a freezer bag; bake from frozen adding 2–4 minutes to the bake time. This makes it easy to have freshly baked cookies anytime without the full prep work. Label with the bake temperature and an estimate of time so you can bake straight from frozen with confidence.

These Cherry Wink Cookies are easy to personalize and reliably popular. Whether you’re making a big batch for a celebration or a small tray for an afternoon treat, their crunchy, fruity character makes them memorable. I hope these cookies find a warm spot in your baking rotation and inspire your own variations.