This post was created as in partnership with Imperial Sugar. All thoughts and opinions are 100% my own.

Both chewy and crunchy with a buttery cookie base, Cherry Winks are a vintage cookie recipe that deserves some renewed attention. Chopped pecans and cornflakes add to the texture, and chopped maraschino cherries and dates add both color and sweetness. These old-fashioned cookies are sure to be a hit on any cookie platter.

I love to look through my collection of vintage cookbooks and revive some long-forgotten favorites. Others you might enjoy are our Cherry Chip Layer Cake, Oatmeal Rolled Sugar Cookies, and Oatmeal Fudge Bars.

A platter of old-fashioned cherry winks on a white plate.

Back in 1950, the original version of these Cherry Winks was submitted by a home baker named Ruth Derousseau from Rice Lake, Wisconsin in the 2nd ever Pillsbury baking contest. Ruth ended up as the Junior Winner with these cookies that have wonderful textural elements as well as a unique flavor.

When making my cherry winks, I wanted to stick pretty close to the original version, but made a couple of changes to suit my tastes. For example, the classic version is made exclusively with shortening, but I swapped that for mostly butter with only a few tablespoons of shortening for texture. You can use one or the other in most recipes, although it's butter that adds the better flavor, while shortening is known for the texture it gives. Sometimes a combo gives the best of both worlds like in these cookies.

I also increased the amount of crushed cornflakes called for in the recipe because 1 and ½ cups crushed cornflakes wasn't nearly enough for my cookies.

Why this recipe works

  • They aren't overly sweet like so many cookies this time of year. The sugar element is more subtle so the naturally sweet flavors of the dates and cherries can come through.
  • No need to chill the dough. It's soft already, so the cornflakes will stick and completely coat the outsides.
  • No need for fancy decorating. Part of the charm of cherry winks is the rustic, craggy look with a sliver or maraschino cherry winking at you from the top of the cookie to make them stand out on a cookie plate!
  • Don't overlook the savory element the cornflakes add to the cookies. Not only do they give texture, but the flavor of cornflakes is quite unique in cookies and goes really well with sweet elements like the cherries and dates.

Ingredient Notes

  • Dates: Be sure to remove the pit or seed from the dates before chopping. Dates are very sticky and soft so feel free to rely on your food processor (affiliate link) to pulse them rather than chopping by hand if that's easier.
  • Maraschino cherries: You love them or you hate them, but in our family we love these brightly colored cherries that come in jars! Look for ones without stems to save yourself the trouble of pulling the stems off before chopping.
  • Cornflakes: These add a fantastic crunch to the outside of the cookies. For a little more sweetness, try using Frosted Flakes instead.
  • Pecans: These add a fantastic crunch and sweetness. You could also use walnuts instead, if you prefer.
Ingredients for making cherry winks on a white surface.

How to Make This Recipe

Start by creaming the butter, shortening, and sugar in a large mixing bowl for 2-3 minutes until light. Add the eggs, milk, and vanilla extract, then mix again until combined. Be sure to stop and scrape the bottom and sides of the bowl so it all gets evenly mixed together.

Add the dry ingredients of the flour, baking powder, baking soda, and salt and mix on low speed just until combined.

Set aside 15 of the maraschino cherries to be sliced into quarters for decorating the tops of the cookies. Pat the remaining maraschino cherries dry before chopping them on a cutting board or pulsing them in a food processor (affiliate link) a couple of times. Remove the hard seed from the middle of the dates, then roughly chop those as well, along with the pecans and add all three of these mix-ins to your cookie dough.

Stir everything together until the fruit and nuts are evenly dispersed. The dough will be quite sticky, which is what you want so that the crushed cornflakes will adhere and completely coat the outside of each cookie.

Roughly crush the cornflakes using a rolling pin (affiliate link), either on a baking sheet or in a heavy duty bag, then transfer them to a shall plate or bowl. Use two teaspoons or a small cookie scoop to drop small tablespoon-sized mounds of the dough directly onto the cornflakes.

Use your fingers to roll the dough into balls that are coated on all sides with the crunchy cereal, then transfer them to a baking sheet lined with parchment paper. Top each ball of dough with a quarter slice of maraschino cherry before baking.

Bake the cookies for 10-12 minutes in a 375°F oven until lightly golden brown around the edges, being careful not to overbake.

For the FULL RECIPE be sure to check out Imperial Sugar's site.

Recipe FAQ's

Why is the dough so sticky?

This dough is intentionally stickier than most cookie doughs thanks to the added milk and the ratio of flour to other ingredients. The purpose is to make sure that the cornflakes adhere really well to coat the outside of every cookie.

What are maraschino cherries?

Maraschino cherries start out as sour cherries that are picked and then brined, then dyed their vibrant color and packed in a sugar syrup to preserve them. They are most frequently used in drinks, but I love to bake with them because we love their slightly almond-y flavor. According to various sources, they seem to have originated in Yugoslavia, Northern Italy or Croatia in the 1800's.

Recipe Tips

  • Storage: The cooled cherry winks can be stored in an airtight container on the counter for about 5-7 days.
  • Freezing: You can freeze these cookies in an airtight container for 2-3 months, then thaw on the counter before enjoying.
  • Don't overmix: Once you add the dry ingredients, don't overwork the dough by beating too much after that or your cookies will end up tough.
  • Don't overbake: I have found that these cookies are particularly prone to going dry if you bake them too long. For a softer, chewier cookie, underbake slightly and remove them from the oven when the edges are just barely brown. They will continue to set up on the pan as they cool.
  • Red and green cherries: Sometimes during the holiday season you can find green maraschino cherries, which would make a fun presentation if you did half of the cookies with green cherries and the other half with red. Although be warned that occasionally the green cherries are mint-flavored instead of the traditional flavor we associate with maraschino cherries.

Be sure to stop by Imperial Sugar’s site for the FULL RECIPE! I have partnered with them now for a few years and love their products for my baking needs!

Cherry, date, and pecan cookies with crushed cornflakes on the outside in front of glasses of milk.

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About the author

Hi, I'm Amy

I enjoy exploring the world through food, culture, and travel and sharing the adventure with mostly from-scratch, family friendly recipes that I think of as modern comfort cooking.

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