Tuesday, May 24, 2022

Caramel-Filled (Rolo) Chocolate Cookies


Back in Jill's 4-H cooking days, she made Rolo Cookies as one of her early fair entries. We called them Surprise Middle Cookies because you weren't supposed to list brand names in 4-H baking. The recipe was always a hit with the judges. The caramel center was a surprise as the judges cut into - or bit into - the chocolaty cookie.

When I was thinking about cookies for Brent's and Susan's rehearsal dinner dessert table, I saw a similar recipe in the Stafford County Hospital Cookbook. It was from Darrell and Shannon Bauer, who own and operate the Wheatland Cafe in the nearby little town of Hudson. They have a stellar reputation for any and all of their cooking - main dish or desserts. And since I couldn't lay my hands on the recipe we'd used for 4-H, I decided to give theirs a try.

They were a success! 

The only difference I can remember is that Jill's 4-H entries were rolled in a combination of granulated sugar and chopped pecans before baking. This particular recipe didn't include the pecans, though that would be an easy substitute.  Since I had other cookies with nuts, I opted to keep these nut free.

Engagement photo by Emily Brensing

These will be part of the cookie spread I'll serve for Brent's and Susan's rehearsal dinner this Friday.

We are looking forward to all the festivities! Exciting times!

Caramel-Filled (Rolo) Chocolate Cookies
Adapted from Stafford County Hospital Cookbook
Working Hands, Caring Hearts
Darrell & Shannon Bauer, Wheatland Cafe
2 1/4 cups all-purpose flour
3/4 cup unsweetened cocoa powder
1 teaspoon baking soda
1 cup butter, at room temperature
1 cup granulated sugar
1 cup light brown sugar
2 large eggs
2 teaspoons vanilla extract
Rolo candies, unwrapped
Granulated sugar, for rolling the cookie dough balls in 
4 oz. almond bark
Sprinkles (optional)
Preheat oven to 350 degrees. Have parchment paper ready to use for cookie sheets.
In small bowl, combine flour, cocoa and baking soda; blend well, and set aside. 
In large mixer bowl, beat sugar, brown sugar and butter until light and fluffy. Add eggs and vanilla; blend well. Add flour mixture and blend until combined and a dough forms. 
Using about 1 tablespoon of dough for each cookie, put an unwrapped Rolo in dough ball, roll it back into a ball, making sure the caramel candy is covered. Roll candy-stuffed cookie ball in granulated sugar and put on parchment-paper-lined cookie sheets. (I used a cookie scoop to measure out the dough for the balls.)

Bake for about 8 minutes or until the cookie ball starts to crack. Remove from oven and allow to cool. 

After cool, melt almond bark. Put in a piping bag or decorator tube and drizzle over cooled cookies. Top with sprinkles, if desired. 

Another option: Sprinkle drizzled cookies with chopped pecans or another favorite nut while the almond bark is still wet.

Note: I used dark cocoa powder.



  1. Have a wonderful weekend and best wishes and congratulations to the happy pair!

    1. Thanks, Helen! We are looking forward to all the festivities!