Brown Sugar & Caramel Cookie Cups

We take tailgating very seriously around here. From the menu to the decorations, we make sure that we do everything in our power to support the Razorbacks. The only thing that we can’t ensure with our carefully-planned tailgates is the score of the game. During the fall, I often play with recipes that are perfect for autumn gamedays. 

Autumn flavors like caramel, cinnamon, and brown sugar were instrumental in crafting this great bite-sized, travel-friendly dessert. Especially caramel. I’ve been on a real caramel kick lately and have had several extra bags of caramel candies laying around waiting to be utilized for something other than a late-night sweet-tooth indulgence. 

We had a fantastic tailgate-themed shower a few weeks back that provided a ton of inspiration for this weekend’s tailgate. Our crafty hostesses served a casual and delicious menu with a backdrop of Arkansas-fabulous accents. I loved the astro-turf tablecloth underneath the food table and these piggy dishes: 

Here’s a close up of those pig dishes: 

And the cute tissue-paper garland made by one of the hostesses: 

When I tailgate, I like to plan a menu that is tasty and unpretentious. I always try to post the menu to avoid having to answer questions about what I’m trying to serve our guests. Here’s our menu from yesterday’s game: 

Despite the torrential downpour, we dined according to plan. We started with a pimento cheese, ranch and fried chicken dip, a garlic-goat cheese herbed spread, and hummus. 

After a brief pause (and a few margaritas), I grilled an Italian-spiced pork tenderloin, bundles of prosciutto-wrapped green beans with Italian dressing and balsamic vinegar, and hot dogs (the only item that Fiance begged for). I also grilled a loaf of sliced french bread with olive oil to enjoy with the tenderloin. The grilled foods were served with a delicious pesto-quinoa salad with grated Parmesan cheese, sauteed eggplant, onions, fresh parsley, and cherry tomatoes.

For dessert, I made these delicious brown sugar cookie cups stuffed with a caramel square. I baked the cookie dough in a mini cupcake tin with a cupcake wrapper because I was worried that the caramel would seep out and burn or otherwise ruin the cookies. These individual bite-sized treats tasted like early autumn and were easy to eat in our rainy tailgate tent. 

Brown Sugar & Caramel Cookie Cups 
Makes 3 dozen cookie cups

You will need:
  • 1 3/4 cups salted butter
  • 1 3/4 cup brown sugar
  • 2 1/4 cups all-purpose flour
  • 1/2 tsp. baking soda
  • 1/4 tsp. baking powder
  • 1/2 tsp. salt
  • 1 tsp. ground cinnamon
  • 2 eggs
  • 1 1/2 tbsp. vanilla
  • 3 dozen caramel squares, unwrapped
  • 3 dozen mini cupcake wrappers
  • Preheat the oven to 350. Line a mini muffin tin with cupcake wrappers. 
  • To brown the butter, place unwrapped butter in a small sauce pan on medium heat. Keep the butter cooking, swirling the pan gently until it begins to brown and it smells nutty and aromatic. 
  • Once the butter has browned, remove from heat. Pour the brown sugar into the sauce pan and mix well. Set the sugar-butter mixture aside to cool for ten minutes or so. 
  • Meanwhile, mix together the flour, baking soda, baking powder, salt, and cinnamon in a medium-sized bowl. 
  • After the butter-sugar mixture has cooled for ten minutes, add it to a large bowl. Stir in the eggs and vanilla. Gradually incorporate the flour mixture. 
  • To make the cookies, wrap a caramel square in a chunk of cookie dough (about two tablespoons of dough). Make sure that the caramel is entirely covered with cookie dough. 
  • Place the cookie dough in the cupcake tin and bake for 12 minutes. 
  • Let the cookie cups cool completely before serving, or enjoy warm while the caramel is still gooey and delicious. 

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