Chewy Cherry Winks: The Vintage Cookie Everyone Loves

Cherry Winks are one of those nostalgic cookies that instantly transport you back to grandma’s kitchen the kind of cookie that looks a little quirky but has a charm you just can’t resist. This recipe first appeared in the 1950s Pillsbury Bake-Off, and it’s easy to see why it became such a hit. They’re chewy in the center, crispy on the outside, and every bite has little surprises like sweet dates, crunchy pecans, and of course, that bright pop of maraschino cherry in the middle.

We love making these during the holidays, but honestly, they’re just as fun any time of year. They’re kid-friendly, freezer-friendly, and always a conversation starter. The best part? They’re super simple to make and even more fun to eat.

Why You’ll Love Cherry Winks

Cherry Winks are cheerful, colorful, and full of textures and flavors that play so well together. That crispy cornflake coating gives way to a chewy center filled with sweet, chewy dates, nutty pecans, and a buttery vanilla base. The cherry in the center gives it that retro look we all secretly love. They’re great for bake sales, cookie swaps, or just a fun baking day with the kids.

Simple Ingredients

Just a few pantry staples and a couple of old-school favorites make this cookie so unique.

• Butter: Brings the rich, creamy base that keeps these cookies soft and flavorful.
• Sugar: Sweetens the dough and balances out the tartness from the cherries.
• Egg: Helps bind the dough and adds a little extra richness.
• Milk: Loosens the dough just enough to keep it soft.
• All-purpose flour: The sturdy base that holds everything together.
• Baking powder: Gives the cookies a little lift so they bake up just right.
• Salt: Just a touch enhances all the sweet flavors.
• Chopped dates: Add a chewy, caramel-like sweetness.
• Chopped pecans: Give a little nutty crunch that pairs so well with the dates.
• Maraschino cherries: The showstopper! Sweet, sticky, and perfectly retro.
• Crushed cornflakes: Roll the dough in these before baking for a crispy golden crust.

Yield & Timing

• Servings: 36 cookies
• Prep Time: 20 minutes
• Cook Time: 10–12 minutes
• Total Time: 35 minutes

What is Needed

• ½ cup butter, softened
• 1 cup sugar
• 2 eggs
• 2 tablespoons milk
• 2¼ cups all-purpose flour
• 1 tablespoon baking powder
• ½ teaspoon salt
• 1 cup chopped dates
• ½ cup chopped pecans
• ⅓ cup chopped maraschino cherries
• 1 cup crushed cornflakes
• Whole maraschino cherries (halved, for garnish)

Instructions

1. Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
2. Cream butter and sugar in a large bowl using a hand mixer until light and fluffy.
3. Add eggs and milk, mixing until smooth.
4. In a separate bowl, whisk together flour, baking powder, and salt.
5. Gradually add dry ingredients to the wet ingredients, mixing until just combined.
6. Fold in chopped dates, pecans, and chopped maraschino cherries.
7. Scoop dough by tablespoonfuls and roll each ball in crushed cornflakes.
8. Place on prepared baking sheet, spacing about 2 inches apart.
9. Top each cookie with a cherry half in the center.
10. Bake for 10–12 minutes, until edges are golden and centers are set.
11. Cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.

Top Tips

• Use a cookie scoop to keep all your cookies the same size this helps them bake evenly.
• Drain the maraschino cherries well before chopping to avoid too much moisture in the dough.
• Crush the cornflakes by hand or in a zip-top bag don’t pulverize them too much; you want texture!
• Let kids help by rolling the dough in the cornflakes and pressing the cherry on top it’s the fun part!
• Freeze some dough balls before rolling in cornflakes so you can have fresh-baked cookies anytime.

Recipe Variations

• Swap pecans for walnuts or leave the nuts out for a nut-free version.
• Add coconut for even more texture and retro flair.
• Use colored cereal flakes around the holidays for a fun twist.
• Try dried cranberries in place of dates for a tarter bite.

Recommended Equipment

• Hand mixer
• Mixing bowls
• Cookie scoop
• Measuring cups and spoons
• Parchment paper
• Baking sheet
• Wire cooling rack

Make Ahead Tips

Make the dough ahead and refrigerate up to 48 hours. Roll in cornflakes just before baking. You can also freeze dough balls (without cornflakes) for up to 3 months.

How to Store and Reheat

Store in an airtight container at room temperature for up to 5 days. For longer storage, freeze baked cookies for up to 2 months. Let thaw at room temp before serving no reheating needed.

What To Serve With This Recipe

• A tall glass of cold milk
• Hot tea or coffee
• As part of a holiday cookie tray
• With a scoop of vanilla ice cream for a retro dessert

What You Need to Know About This Recipe

Cherry Winks first became popular after winning a Pillsbury Bake-Off in the 1950s. They’re a true reflection of mid-century baking: fun, colorful, a little unconventional, and totally crowd-pleasing. The addition of cornflakes as a coating was inventive at the time and still adds that delightful crunch today. If you love vintage recipes with charm and character, this one’s a must-try.

More Christmas Cookies

If you love these cookies you must try these forgotten Christmas Cookies.