• Suzanne Yearley

Deeply-Chocolate, Caramel Cookies for your Holiday Cookie Plate or Anytime

December 21, 2017

Suzanne Yearley

Cookies make people happy.  Whether it is a group of friends sharing a cookie plate after a meal, a plate of cookies on the counter as an after school treat, or a holiday cookie display; the act of sharing cookies brings people together and is just plain fun. There is no one thing that makes a cookie recipe appealing. Chocolate, oatmeal, raisin, candy, cereal, lemon, vanilla, sugar; I love them all! Mixing high and low also doesn’t matter here: some of the finest restaurants in the world serve warm chocolate chip cookies and milk for dessert while delicate wafer cookies are available at a kiosk at the mall. The ultimate cookie from the grocery aisle is the ubiquitous rice krispy treat that many of us grew up on and still secretly love. At the opposite end of the spectrum, there are Parisian macaron whose pastel color palette and light texture make any occasion elegant.

What is it that makes each of these delicious and oh-so-appealing? Perhaps it is the way that we eat cookies that creates our unique passion for these sweets. I like to break off pieces a little at a time while others opt for picking one up and taking a big bite. There are always the dunkers: who prefer to dip each morsel into a glass of milk, hot tea, or a cappuccino.

However you enjoy your cookies, I think you will love these. This recipe is adapted from one that I had at Mountain Sky guest ranch in Montana. They had delicious cookies in general, or perhaps it was the miles of mountain hiking and horseback riding that made everything taste better. Nonetheless, there is something about this chocolate dough wrapped around a caramel Rolo that makes them irressistable. I have upped the ante a little and made the dough more chocolately and less sweet then the original, also adding a little milk to make it easier to work with. Regardless, the key here is getting a nice seal when wrapping the Rolo. Be careful not to burn your fingers on any oozing caramel. It is hard to resist digging right in, but your friends and family will thank you as they enjoy these together this holiday season or all year-round. Merry Christmas to all!

Secrets to Success:

  • To avoid tough cookies, measure flour properly, do not over-mix, or over-bake.

  • To measure flour: use a scoop, cup or spoon to transfer the flour into the measuring cup. Never scoop the cup into the flour container as this compresses the flour and gives you more than you need.

  • To avoid over-mixing: when adding the dry ingredients keep the mixer on the lowest speed and turn it off when the dough just comes together.

  • Do not use Dutch-Process cocoa but regular Hershey’s or similar un-dutched cocoa here.

  • The key is carefully wrapping the Rolo in the chocolate dough to prevent oozing.

  • A Silpat silicon baking sheet makes for easy clean-up.

  • Use crystalized decorative sugar when rolling the cookies for an even more distinctive crunch.

  • Cookies should still be soft when removed from the oven. Cool them on the baking sheet so they continue to set.

Nancy’s Rolo Cookies

Adapted from The Mountain Sky Guest Ranch Cookbook


1 cup (2 sticks) butter at room temperature

1 cup sugar

1 cup brown sugar

1 tablespoon pure vanilla extract

2 eggs

1 tablespoon mik

1 1/4 cups Hershey’s cocoa powder

2 1/4 cups flour

1 teaspoon baking soda

1 teaspoon salt

Rolo candies

Sugar for rolling the cookies


In a large bowl, cream together butter and sugars. Add the eggs, one at a time, mixing well after each addition and stopping to scrape down the sides of the bowl in between. Beat in the vanilla and milk, and blend well. In another bowl, mix together flour, cocoa powder, baking soda and salt. With the mixer on the lowest speed, add the dry ingredients to the mixer and mix just until combined. Chill the dough for 30-60 minutes.

Roll cookie dough into 1 1/4-inch balls, and press Rolo candy into center covering candy completely. Roll in sugar, bake on cookie sheets in a preheated 350^F. oven for about 12 minutes, until set but quite soft. Cool on the baking sheets so cookies continue to firm yet remain soft inside. Yield 24-30 cookies.


make ahead



lunch box






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