Living in Cincinnati is funny. I live and work in Ohio but buy my groceries and get gas in Kentucky. Even the Cincinnati airport is located in Kentucky. I often forget I’m changing states when I cross the river, but once you hit Kentucky you can feel that you’re in the South. One of the best parts of living in Cincinnati is being close enough to the South to to celebrate southern traditions and events such as The Kentucky Derby.
There are many traditions associated with the Kentucky Derby from big hats and fancy dresses to the playing of ‘My Old Kentucky Home,’ but my favorite tradition involves pie.
Derby Pie®, a walnut and pecan pie with the addition of chocolate and bourbon, was originally made in the 1950s at a restaurant just outside Louisville called The Melrose Inn. The owners, Walter and Leondra Kern, perfected the recipe and eventually needed to choose a name. To do so, they had all of their family members write suggestions down and Derby Pie ® was the winner out of the hat. The family eventually started a pie business called Kern’s Kitchen and it is now the official baker of Derby Pie ® and sells nearly 150,000 pies a year.
The name Derby Pie ® has been trademarked by Kern’s Kitchen and they have filed many lawsuits to protect the name. In Kentucky (and in cookbooks and magazines), you’ll see variations of the pie going by names such as Chocolate Nut Pie, May Day Pie, Horse Race Pie, NOT Derby Pie, or Pegasus Pie.
I love the tradition of Derby Pie ® more than I like the actual pie. The sweet filling, boozy bourbon, buttery nuts, and rich chocolate make for a dessert that is just too rich for me and I can only manage a few bites. This year, I decided to make something that would take the flavors of the Derby but make them a little more balanced… after all, I like to eat lots of dessert and not just a few bites.
Looking through some books (specifically Cookie Love by Mindy Segal), I was inspired by thumbprint cookies and knew the shortbread would be the perfect balance to the sweet bourbon-chocolate filling. The shortbread is a traditional recipe but I substituted some of the flour with ground pecans to give it a more nutty flavor before filling the thumbprints with a chocolate, bourbon, and pecan mixture. These cookies are quick to make and easier to serve at a party than slices of pie. If you’re looking for a new Derby tradition, give Kentucky Derby Cookies a try.
An additional note: At the bottom of this post, right before the comments, you may notice a new orange ‘Yum’ button. This button comes from a new website called Yummly where I’ve recently joined their team of publishers (you can find my publisher page here). Yummly allows you to save recipes from all over the web in one convenient ‘recipe box’ hosted on their site. You can search your recipe box, browse the site for new recipes, and even create a grocery list. I’ve been using Yummly for the past few weeks and I’ve found it really helpful. Consider joining Yummly so the next time you see a recipe you like on this site (or any site) you can hit the Yum button and save it to your recipe box.
Kentucky Derby Cookies
Let’s talk through the recipe before we start baking. The recipe is relatively easy but there are a few things to go over to make it foolproof.
Here’s something to consider before you start baking – you will have extra filling left over. You can either double the shortbread recipe and bake around 40 cookies or you can save the extra filling in a jar and use it for a sauce over vanilla ice cream. It will keep for a few days in the refrigerator but may need to be warmed slightly until it is pourable.
When you’re ready to start baking, the first thing you’ll want to do is toast the pecans that will be ground up and mixed into the shortbread dough. (You also need toasted pecans for the filling so you can toast those at this time too as long as you are sure to only grind half of them.)
To toast the nuts, simply spread the pecans out on a baking sheet and put them in a 350-degree oven for 8-10 minutes. You’ll want to keep an eye on them because nuts can burn quickly. They are done when they look lightly toasted and are fragrant.
Let them cool for a few minutes, then use a food processor to grind them to nearly a powder. I pulse them until they are finely ground and no big pieces remain. Try not to grind them too far or the oils will release and the meal will become mushy. If you want to ensure the pecans are smooth with no pieces remaining, run the pecan meal through a fine mesh strainer or flour sifter.
Now, it’s time to make the shortbread dough. This part is easy but one trick that makes a big difference is to scrape down your mixer bowl several times throughout the process. Usually, I scrape down the bottom and the sides between each step or before I add a new ingredient.
Using a stand mixer (or a handheld electric mixer), cream together the butter and sugar until light and fluffy. Then, mix in the vanilla extract, bourbon, and salt until combined. Dump in all of the flour and ground pecans at once and mix on low speed just until the dough comes together and no dry patches remain. Dump the dough out onto a piece of plastic wrap, press it into a square, wrap it up, and refrigerate it for at least 30 minutes or until it is firm.
While the dough is chilling, you can make the filling. Start by melting the butter and then stirring in light corn syrup, brown sugar, salt, and chocolate chips.
Here’s a trick: when you’re measuring a sticky ingredient such as corn syrup, molasses or honey, spray the inside of your measuring cup with cooking spray. The sticky syrup will slide right out and clean up is a breeze.
Once everything is melted, add the heavy cream and let the mixture simmer and thicken for a few minutes. When it’s thick enough to coat the back of a spoon, stir in the pecans, bourbon, and vanilla extract. You don’t want to stir in the bourbon and vanilla extract until the end or some of it will cook off and you’ll lose flavor.
Once the filling is cool enough to taste, take a spoonful and decide if you want to increase the amount of bourbon. Whenever I cook with booze, I start small and add more gradually, making sure to taste in between every addition. I don’t want my cookies tasting like shots of liquor!
When the dough has finished chilling, roll 1 tablespoon portions of dough into balls. Place each ball on a baking sheet and use your thumb to press down and form an indentation in the center of the dough. You can also use your fingers to help make the well by pressing the sides of the cookies to form a sort of wall for the filling.
When the cookies are baking, the centers tends to puff up so use a wooden spoon to press the centers down when you rotate the pans half way through baking. Once you remove the cookies from the oven, repeat the process and punch down the centers again with the end of a wooden spoon.
This is how the dough should look before it goes in the oven
Let the cookies cool until you are able to handle them. Fill the center of each cookie with the chocolate filling, about 1 tablespoon in each cookie. Don’t worry if some drips over the sides. Let the cookies sit for a few minutes so the filling can set up. These will last for 2-3 days if kept in an airtight container.