This recipe has followed me through cookie swaps, holiday trays, and lazy afternoon baking sessions. I first made these Cherry Wink Cookies on a rainy December afternoon when I wanted something both crunchy and fruit-forward to break up the usual chocolate-laden plate. The first bite—crisp cornflake exterior yielding to a tender, nutty interior with a sweet wink of cherry—was such a pleasant contrast that I started keeping the ingredients on hand year round. These cookies are more about texture and balance than overly sweet glaze; they deliver crunchy, chewy, and fruity notes in every bite.

What makes this version special is the use of crushed cornflakes twice: once in the dough for a subtle crunch and once as a coating for that satisfyingly brittle edge. I also fold in chopped dates and pecans for deep caramel notes and nutty structure, and a small quartered maraschino cherry tops each cookie for a cheerful finish. The technique is straightforward, the baking forgiving, and the result reliably crowd-pleasing. I often bring a tin to potlucks and receive surprised questions about how the texture is so unique—then I tell them it’s the cornflakes trick.

Ingredients

• All-purpose flour: 2 cups. Use a spoon-and-level method for accurate measurement; King Arthur or Gold Medal work well. Flour provides structure and keeps the cookies tender when balanced with cornflakes.
• Cornflakes: 1 cup, finely crushed in the dough and an additional 2 cups roughly crushed for coating. Use a plain cornflake variety without added sugar for the best contrast.
• Baking powder and baking soda: 1 teaspoon baking powder and 1/2 teaspoon baking soda. Together they give a gentle lift and create a light interior while the coating stays crisp.
• Shortening and granulated sugar: 1 cup shortening and 1 cup sugar. Shortening helps the cookies hold their shape and stay crisp at the edges; use a neutral vegetable shortening.
• Eggs, half-and-half, and vanilla: 2 large eggs, 2 1/2 tablespoons half-and-half, and 1 1/4 teaspoons vanilla extract. These wet ingredients bind the dough and add richness and aroma.
• Pecans and dates: 1 cup pecans, roughly chopped, and 1 cup pitted dates, roughly chopped. Pecans add toasted flavor and dates add chewy, caramel notes.
• Maraschino cherries: 1/3 cup finely chopped and patted dry for the dough, plus 15 quartered cherries for topping. Pat them dry on paper towels to avoid excess moisture that can make the dough loose.
• Salt: 1/2 teaspoon to balance sweetness — do not omit.

Instructions

Preheat and prepare: Preheat the oven to 375°F. Line baking sheets with parchment paper and arrange racks in the center of the oven. Have a tablespoon scoop, two bowls for crushed cornflakes, and a cooling rack ready. Baking sheets should be cool between batches to maintain even browning. Mix dry ingredients: In a medium bowl, whisk together 2 cups all-purpose flour, 1 cup crushed cornflakes, 1 teaspoon baking powder, 1/2 teaspoon baking soda, and 1/2 teaspoon salt until evenly combined. Crushing the cornflakes fine in the dough helps them integrate without large flakes shredding the structure. 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. This step incorporates air for a lighter bite; shorten the time if you prefer a denser cookie. Add eggs and liquids: Reduce speed to low and add eggs one at a time, mixing well after each addition. Add 2 1/2 tablespoons half-and-half and 1 1/4 teaspoons vanilla extract and mix just until incorporated. Overmixing will develop gluten and toughen the cookie. Combine and fold: With the mixer on low, gradually add the dry mixture and mix until just combined. Fold in 1 cup chopped pecans, 1 cup chopped pitted dates, and 1/3 cup finely chopped, patted-dry maraschino cherries by hand to keep the texture tender and prevent overmixing. Scoop and coat: Using a tablespoon scoop, portion dough and roll each scoop in the 2 cups of roughly crushed cornflakes until completely coated. Shape lightly into a ball and place on the prepared baking sheet about 2 inches apart to allow for slight spread. Top and bake: Press a quartered maraschino cherry into the center of each dough ball. Bake 10 to 12 minutes or until the bottom edge is golden. Rotate the sheet once halfway through for even browning if your oven has hot spots. Cool: Let cookies rest on the baking sheet 2 to 3 minutes to set, then transfer to a cooling rack until completely cool. Cooling on the sheet slightly helps the cookie interior finish cooking without overbrowning the base.

Storage Tips

Store cooled cookies in an airtight tin at room temperature for up to 5 days. Place a sheet of parchment between layers to prevent sticking. If you need longer storage, freeze in a single layer on a baking sheet until firm, then transfer to a freezer-safe container for up to 3 months. Reheat briefly in a 300°F oven for 5 minutes to refresh the cornflake crunch. Avoid refrigeration, which can introduce moisture and soften the coating.

Ingredient Substitutions

For a lighter fat profile, you can replace half the shortening with unsalted butter; expect slightly more spread and a richer flavor. To make these nut-free, omit the pecans and increase dates by 1/2 cup or add sunflower seeds for crunch. Use full-fat milk instead of half-and-half if needed; reduce liquid by 1/2 teaspoon to keep the dough from becoming too loose. For a gluten-free version, substitute a 1-to-1 gluten-free flour blend and ensure cornflakes are certified gluten-free.

Serving Suggestions

Serve these on a dessert platter with a mix of plain and festive cookies. They pair well with black coffee or a lightly sweetened tea. For a party, arrange on a tiered tray and garnish with fresh cherries or mint sprigs. Their bright cherry top makes them ideal for holiday cookie swaps and festive gatherings. For a grown-up touch, serve alongside a small glass of sherry or amaretto.

Cultural Background

Cookies topped with maraschino cherries have a mid-20th century American pantry-cookery feel, featuring convenience ingredients like store-bought cherries and flakes. The technique of crushing cereal for texture harkens back to vintage family recipes that made use of accessible breakfast cereals to add crunch. These cookies are a modern take that balances old-fashioned charm with updated ingredients like dates for natural sweetness instead of all glaze or frosting.

Seasonal Adaptations

In winter, swap maraschino cherries for finely chopped candied citrus peel and top with a piece of glace cherry for holiday color. In summer, use dried tart cherries rehydrated briefly and patted dry for a brighter fruit acidity. For autumn, replace dates with chopped dried figs and swap pecans for walnuts, dusting lightly with cinnamon for seasonal warmth.

Meal Prep Tips

Prepare the dough up to 24 hours ahead: scoop and roll dough balls, then chill on a tray covered in plastic wrap. When ready to bake, quickly roll in crushed cornflakes and proceed with baking time. This step saves active time on the day of serving. Baked cookies can be portioned into small resealable bags for lunches or party favors. If transporting, nest in parchment-lined boxes to avoid crushing the cornflake coating.

Whether you make these for a special occasion or a quiet afternoon treat, the combination of textures and the cheerful cherry on top make these cookies a recipe I return to again and again. Enjoy baking and sharing them with people you love.