Cherry Winks

There are cookies that are trendy, and then there are cookies that feel like a cherished heirloom, passed down through generations. Cherry Winks are absolutely the latter. They are a vintage treasure from the 1950s, a soft, chewy, fruit-and-nut-filled cookie rolled in crunchy cornflakes and topped with a single, bright maraschino cherry that “winks” at you from the plate. Every bite is a perfect balance of textures and a taste of pure nostalgia.

Why You’ll Love This Recipe

This cookie has a story. It was created by a young home baker named Ruth Derousseau from Rice Lake, Wisconsin, and won Junior First Prize at the second-ever Pillsbury Bake-Off in 1950. For decades, it was a staple on holiday cookie platters, and it deserves a grand comeback.

What makes Cherry Winks so special is their unique combination of flavors and textures. The cookie itself is lightly sweet, allowing the natural sweetness of the chopped dates and cherries to shine. Then, you get the satisfying crunch from the pecans and the toasted cornflake coating, which gives way to a soft, cake-like interior. And of course, that final quarter of a maraschino cherry on top adds a festive pop of color and a little wink.

Ingredients

2 ¼ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon salt
¾ cup unsalted butter (or shortening), softened
1 cup granulated sugar
2 large eggs
2 tablespoons milk
1 teaspoon vanilla extract
1 cup chopped pecans
1 cup chopped dates
⅓ cup chopped maraschino cherries, patted very dry
2 ½ cups cornflakes, coarsely crushed
15 maraschino cherries, quartered, for topping

Directions

Preheat your oven to 375°F (190°C). Grease or line your baking sheets with parchment paper.
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
In a large bowl, cream the butter and sugar together until light and fluffy. Beat in the eggs, then the milk and vanilla.
Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
Gently fold in the chopped pecans, dates, and the ⅓ cup of chopped maraschino cherries.
Place the crushed cornflakes in a shallow dish. Roll rounded tablespoonfuls of dough into balls, then roll each ball in the cornflakes until fully coated. Place them on the prepared baking sheets.
Press a quarter of a maraschino cherry into the top of each cookie.
Bake for 10-12 minutes, until the cookies are set and the cornflakes are lightly golden. Be careful not to overbake; they are meant to be soft and chewy.
Let them cool on the baking sheet for a minute before transferring to a wire rack to cool completely.

Expert Tips

Dry Your Cherries: The most important tip is to pat the chopped maraschino cherries very dry with paper towels. Excess moisture can make the dough sticky and difficult to work with.
Don’t Overmix: Mix the dough just until the flour disappears. Overmixing will develop gluten and result in a tough, dense cookie.
Coarse Cornflakes: Crush the cornflakes with your hands, aiming for small flakes and fragments, not a fine dust. This keeps the coating crisp and textured after baking.
A Touch of Shortening: While you can use all butter, the original recipe uses shortening. Using a mix of butter (for flavor) and a few tablespoons of shortening (for texture) gives you the best of both worlds.
Don’t Overbake: Pull them from the oven as soon as the edges are lightly golden. They will continue to set on the pan as they cool.

Storage and Reheating

Store cooled Cherry Winks in an airtight container at room temperature for up to a week. For longer storage, they freeze beautifully for up to two months. There’s no need to reheat them; they are delicious at room temperature or even slightly chilled.

Frequently Asked Questions

What are Cherry Winks? They are a classic American drop cookie made with a spiced dough, chopped dates, pecans, and maraschino cherries, rolled in crushed cornflakes and topped with a cherry quarter.
Who invented Cherry Winks? The recipe was created by Ruth Derousseau of Rice Lake, Wisconsin, and won the Junior First Prize at the 1950 Pillsbury Bake-Off.
Can I use fresh cherries instead of maraschino? Maraschino cherries are traditional and give the cookie its signature look and sweet flavor. Fresh cherries would add too much moisture.
Why are my cookies dry? They were likely overbaked. For a soft, cake-like texture, err on the side of underbaking and remove them when the edges are just barely golden.
Can I make these without nuts?Yes. You can simply omit the pecans or substitute them with something like sunflower seeds for a nut-free version.

What to Serve With This Dish

A hot cup of tea or coffee for a classic pairing.
A cold glass of milk.
As part of a festive holiday cookie platter.
A scoop of vanilla ice cream for an extra indulgent dessert.

Final Thoughts

Cherry Winks are more than just a cookie; they are a delicious piece of baking history. They are proof that a simple, honest recipe can stand the test of time. I hope you bring a batch of these charming, winking cookies into your kitchen and create some new memories of your own.