This batch of Cherry Wink Cookies has lived in my holiday rotation for years. I first learned this version from a neighbor who brought a tin to a block party the winter after I moved into my house. The cookies were the kind that disappeared first: crisp at the edges, slightly chewy in the center, studded with chopped dates and pecans, and finished with a tiny, glossy cherry that made each cookie look like a little celebration. I adapted the recipe over time to emphasize texture contrast and to keep the cherries from bleeding into the dough.

I make these when I want a cookie that feels old-fashioned but still fresh. The cornflake coating adds a satisfying crunch that plays against the softer interior, and the maraschino cherry on top brightens every bite. They travel well, freeze beautifully, and are a favorite with kids and adults alike. Every time I bring a plate to a gathering someone asks for the recipe, and the simple charm of a cherry perched on a golden cookie never fails to draw compliments.

Ingredients

• All-purpose flour: Use 2 cups of good-quality all-purpose flour for structure. I like King Arthur or Gold Medal; whisk it well to remove lumps so the dough mixes evenly.
• Cornflakes (for dough): 1 cup finely crushed cornflakes folded into the dry mix add lightness and a hint of toasted flavor. Use plain, unsweetened cornflakes rather than frosted varieties.
• Baking powder and baking soda: 1 teaspoon baking powder and 1/2 teaspoon baking soda provide the mild lift these cookies need without becoming cakey.
• Salt: 1/2 teaspoon to balance the sweetness and enhance flavors.
• Shortening and sugar: 1 cup shortening and 1 cup granulated sugar make a tender, slightly crisp cookie; shortening yields a reliably crisp edge and soft center.
• Eggs: 2 large eggs at room temperature for proper emulsification and structure.
• Half-and-half: 2 1/2 tablespoons for added richness; whole milk works in a pinch but half-and-half gives a silkier mouthfeel.
• Vanilla extract: 1 1/4 teaspoons of pure vanilla for depth of flavor; if using imitation, reduce slightly.
• Pecans and dates: 1 cup chopped pecans and 1 cup chopped pitted dates give texture and a caramel-like sweetness that complements the cherry.
• Chopped maraschino cherries: 1/3 cup, finely chopped and patted very dry to prevent sogginess in the dough.
• Cornflakes (for coating): 2 cups roughly crushed to coat the cookie dough so the exterior bakes up crunchy and attractive.
• Maraschino cherries for topping: 15 cherries, patted dry and quartered, one placed on each cookie for the classic wink appearance.

Instructions

Preheat and prepare:Preheat the oven to 375 degrees Fahrenheit. Line baking sheets with parchment paper and set aside. Allow the eggs to come to room temperature for at least 15 minutes beforehand for better mixing.Whisk dry ingredients:In a medium bowl, whisk together 2 cups all-purpose flour, 1 cup finely crushed cornflakes, 1 teaspoon baking powder, 1/2 teaspoon baking soda, and 1/2 teaspoon salt. Whisking distributes leavening evenly and helps prevent pockets of baking soda.Cream shortening and sugar:In a separate mixing bowl or stand mixer fitted with a paddle, beat 1 cup shortening and 1 cup granulated sugar on medium-high for about 1 to 1 1/2 minutes until blended and slightly lighter. This short creaming step incorporates enough air for lift without overwhipping, which can make cookies spread too much.Add eggs:Lower mixer speed to low and add the eggs one at a time, mixing well after each addition. This gradual method ensures the eggs emulsify into the fat and prevents a curdled appearance.Flavor and richness:Mix in 2 1/2 tablespoons half-and-half and 1 1/4 teaspoons vanilla extract just until combined. Avoid overmixing to preserve tender texture.Combine mixtures:With the mixer on low, slowly add the flour mixture and mix only until just combined. Overmixing at this stage develops gluten and can toughen the cookies.Fold in mix-ins:Using a spatula, gently fold in 1 cup chopped pecans, 1 cup chopped dates, and 1/3 cup chopped, well-drained maraschino cherries. Ensure even distribution but resist long folding.Portion and coat:Use a 1 tablespoon scoop to portion dough. Roll each scoop between your hands if needed, then roll each ball in the 2 cups roughly crushed cornflakes until fully coated. Place coated balls about 2 inches apart on the prepared baking sheets and press one quartered cherry into the center of each ball.Bake and cool:Bake for 10 to 12 minutes, or until the bottom edge is golden. Remove pans to a wire rack and let cookies rest on the sheet 2 to 3 minutes before transferring to the rack to cool completely. This short rest allows cookies to set and prevents breaking when moved.

Storage Tips

Store completely cooled cookies in an airtight container layered between sheets of parchment to prevent sticking. At room temperature they will remain at peak texture for 3 to 5 days. For longer storage, freeze baked cookies in a single layer on a tray until firm, then transfer to a sealed freezer container for up to 3 months. To refresh the crispness after thawing, warm cookies in a 300 degree Fahrenheit oven for 3 to 5 minutes, watching carefully so the cherries do not overcook.

Ingredient Substitutions

If you need to adjust ingredients, substitute butter for shortening on a one-to-one basis for richer flavor, though the texture will be slightly less crisp at the edges. For a dairy-free version, use a non-dairy creamer or coconut cream instead of half-and-half and a vegan shortening. To make them gluten-free, swap the all-purpose flour for a 1-to-1 gluten-free flour blend and choose gluten-free cornflakes. If you do not have dates, chopped dried apricots or raisins provide a similar chew and sweetness.

Serving Suggestions

These are perfect plated with coffee or a simple hot chocolate. For a seasonal twist, dust with a light coating of powdered sugar for winter gatherings or serve alongside a bowl of whipped cream sweetened with a touch of vanilla. They make a cheerful addition to cookie trays and gift tins, and are small enough to be served with afternoon tea or as a light dessert after a family meal.

Cultural Background

The idea of a cherry-topped cookie taps into classic American midcentury baking traditions where bright maraschino cherries were used as garnish for cakes and confections. These small cookies are reminiscent of vintage cookie recipes that paired nuts and dried fruits with crisp coatings for contrast. They were popular at church socials and community bake sales where portability and shelf life were prized.

Seasonal Adaptations

For summer, try using jarred maraschino cherries drained and rinsed to remove excess syrup, or swap in glacé cherries for a richer flavor. For the holidays, add a pinch of cinnamon to the dry mix and sub in chopped crystallized ginger for the dates. Around autumn, substitute toasted walnuts for pecans and fold in a tablespoon of molasses for warmth. Small changes in mix-ins change the cookie character while keeping the same dependable technique.

Meal Prep Tips

Prepare and portion the dough ahead: scoop and roll into balls, coat with cornflakes, and freeze on a sheet tray. Once frozen, store in a sealed bag. Bake straight from frozen, adding 1 to 2 minutes to the bake time. This makes fresh-baked cookies available on short notice for unexpected guests or quick dessert needs. Label containers with dates and bake one test cookie to verify timing when using frozen dough.

These Cherry Wink Cookies celebrate simple pantry ingredients with a nostalgic presentation. They are easy to make, adaptable, and delightfully crunchy. Share them with neighbors, pack them for lunches, or keep a tin on the counter for a quick, cheerful treat.