Cherry Winks Cookies

Cherry winks cookies combine chopped dates, pecans, and maraschino cherries in a soft cookie with a crunchy cornflake coating and a bright cherry top.

With their red cherry “winks” and craggy golden edges, these cookies bring a cheerful, old-fashioned look to a holiday plate. Inside, chopped dates provide chewy pockets of sweetness, pecans contribute a nutty bite, and maraschino cherries add color throughout the dough. The cornflakes go on the outside, where they create a contrasting texture as the cookies bake. Set out the coating and toppings before you begin shaping so the final assembly feels organized. This is a straightforward batch to prepare in stages while the first sheet is in the oven.

Why You’ll Love This Recipe

• Each cookie has a crunchy cornflake exterior and a tender center.
• Dates, pecans, and cherries make every bite interesting.
• The cherry quarter on top is an easy, colorful decoration.
• No rolling pin or cookie cutters are needed.
• The small portions fit neatly into mixed cookie boxes.

Recipe Details

Oven: 375°F. Baking time: about 10–15 minutes per batch. Allow about 30 minutes for mixing, shaping, and coating, plus cooling time. The 15 quartered topping cherries provide 60 pieces, so aim for about 60 small cookies if you want one quarter on every cookie. That yield is an estimate; the size of the dough balls determines the final count.

Ingredients

• 1 cup sugar
• ¾ cup shortening
• 2 tablespoons milk
• 1 teaspoon vanilla
• 2 eggs
• 2¼ cups all-purpose flour
• 1 teaspoon baking powder
• ½ teaspoon baking soda
• ½ teaspoon salt
• 1 cup chopped pecans
• 1 cup chopped dates
• ⅓ cup chopped maraschino cherries
• 1½ cups coarsely crushed cornflakes
• 15 maraschino cherries, cut into quarters, for topping

The chopped cherries mixed into the dough are separate from the 15 cherries used for the tops. Drain and blot both portions before using so excess syrup does not make the dough wet. Chop the dates and pecans into small pieces for easier shaping. Crush the cornflakes coarsely; a few irregular flakes create a more distinct coating than a bowl of fine cereal powder.

Numbered Instructions

1. Prepare for baking. Heat the oven to 375°F and line baking sheets with parchment paper. Put the crushed cornflakes in a shallow dish and keep the quartered topping cherries nearby.
2. Cream the base. Beat the sugar and shortening together until evenly combined and creamy. Scrape down the bowl, then mix in the milk, vanilla, and eggs until the mixture is uniform.
3. Add the dry ingredients. Whisk the flour, baking powder, baking soda, and salt in another bowl. Add to the shortening mixture and mix just until the flour disappears. Scrape the bottom of the bowl to check for hidden dry pockets.
4. Fold in the fruit and nuts. Stir in the chopped pecans, dates, and ⅓ cup chopped maraschino cherries. Distribute them evenly without continuing to beat the dough once everything is incorporated.

5. Shape and coat. Form small, evenly sized balls of dough. Roll each in the coarsely crushed cornflakes, pressing lightly so the coating clings. Place on the lined sheets, leaving room for spreading. Gently press a cherry quarter onto the top of each ball.

6. Bake until lightly golden. Bake for about 10–15 minutes, checking the first tray near the shorter end of the range. The edges and cornflakes should look lightly golden, and the centers should appear set. Do not wait for deep browning across the entire cookie.
7. Cool carefully. Let the cookies rest on the baking sheet until firm enough to lift without bending. Move to a wire rack with a spatula and cool completely before packing. Repeat with the remaining dough, using cooled baking sheets for each batch.

Helpful Tips

Moisture control begins with the cherries. Blotting them before chopping keeps syrup from pooling on the cutting board and entering the dough. If the dates stick together, separate the pieces as you fold them in so one cookie does not end up with a large, dense clump.

Portion the dough before coating whenever possible. This helps you see whether the batch will match the available cherry quarters. Keep the portions close in size so a few oversized cookies do not need extra oven time after smaller ones are done. If the dough gets very soft, briefly chill it until shaping is comfortable.

Press the topping cherry into the surface just enough to anchor it. A deep push can flatten the ball or dislodge the cornflakes. When coating, use a gentle rolling motion rather than squeezing, which can crush the cereal into fine crumbs.

Variations

Change the appearance by leaving the cornflakes fairly craggy or crushing them a little more evenly. Keep the total measured coating the same. A finer coating looks tidier, while larger flakes emphasize the crunchy texture.

You can chop the dates and pecans more finely for smaller cookies or leave a little more texture in a larger portion. Keep the fruit and nut quantities unchanged, and begin checking early when making smaller cookies. Arrange every cherry quarter with the cut side down for a consistent finishing touch.

Storage Advice

Store fully cooled cookies in an airtight container at room temperature for about 4 days. Place parchment between layers to protect the cherry tops and cornflake coating. The coating is crunchiest when fresh and may soften a little as moisture moves through the cookies during storage.

Freeze cooled cookies for up to 2 months in a tightly sealed container, using parchment to separate layers. Thaw while covered at room temperature before serving. For gift boxes, pack the cookies snugly enough to prevent sliding, but avoid placing heavy treats on top of their crisp cereal edges.