These prize-winning Chocolate Caramel Rolo Cookies are a family favorite. They’re an easy to make, rich, fudgy chocolate cookie stuffed with a Rolo candy.
My family is crazy about these cookies and we’ve been making for years. The cookie recipe was a $2,000 winner in the 1990 Pillsbury Bake-off. Stuffing a Rolo candy inside a chocolate cookie was a brilliant idea. How can you go wrong with the combination of chocolate and caramel.
I originally posted these cookies in August 2008, the first year I started blogging. I’ve been trying to update my posts with better pictures, so when my husband made them again recently, I took some much better pictures.
Making Chocolate Caramel Rolo Cookies
When making these cookies, it’s important to place the Rolo near the top of the cookie dough. I like to use a #40 scoop and make a round ball. Then set the Rolo on top of the dough and push the dough up around the Rolo to cover it.
You want a nice thick base of cookie dough underneath the Rolo. The Rolo will melt while baking, and the more dough underneath the Rolo, the less likely it will be to leak out of the bottom.
It’s also important to use parchment paper or a Silpat when baking these cookies so they don’t stick to your baking sheet.
These cookies are better if slightly underbaked.
I’m not a nut lover, so when my husband made them this time, he omit nuts on half of them for me. He’s crazy about nuts and added pecans to his half.
Either way, if you haven’t baked a Rolo cookie before, you need to get on that asap.
Chocolate Caramel Rolo Cookies
Ingredients
- 2 ½ cups flour Pillsbury BEST® All Purpose or Unbleached Flour
- ¾ cup unsweetened cocoa
- 1 teaspoon baking soda
- 1 cup sugar
- 1 cup firmly packed brown sugar
- 1 cup margarine or butter softened
- 2 teaspoons vanilla
- 2 eggs
- 1 cup chopped pecans or walnuts
- Rolo® Chewy Caramels in Milk Chocolate unwrapped
- 1 tablespoon sugar
Instructions
- In a medium bowl, combine flour, cocoa, and baking soda; mix well.
- In a large bowl, combine 1 cup sugar, brown sugar, and margarine; beat until light and fluffy. Add vanilla and eggs; beat well. Add flour mixture; blend well. Stir in ½ cup pecans if using.
- Cover the bowl with plastic wrap and refrigerate the dough for 30 minutes for easier handling.
- Preheat oven to 375°F. Line baking sheets with parchment paper or a Silpat.
- For each cookie, with floured hands, shape about 1 tablespoon dough around 1 Rolo candy, covering completely. **
- In a small bowl, combine the remaining ½ cup pecans and 1 tablespoon sugar. Press one side of each ball into pecan mixture. Place, nut side up, 2 inches apart on ungreased cookie sheets.
- Bake at 375°F. for 7 to 10 minutes or until set and slightly cracked. Cool 2 minutes; remove from cookie sheets. Cool on wire rack for 15 minutes or until completely cooled.
Notes
**When making these cookies, it’s important to place the Rolo near the top of the cookie dough. I like to use a #40 scoop and make a round ball. Then set the Rolo on top of the dough and push the dough up around the Rolo to cover it.
Nagi@RecipeTinEats
I will definitely try to make this as soon as possible!
kristy
I am drooling. Wish I can have a couple of them right now. Yummm…. I think I’ll try one with toffee candy >o<
Have a great week ahead dear.
Blessings, Kristy
Carol
Oh my goodness……emphasis on GOODNESS! Those look dangerous in a good way. And don’t I have Rolos in the freezer. Uh oh….I feel some cookie baking coming on. 🙂
I love the old Pillsbury Bake Off recipes-I have 2 Best of the Bake-Off cookbooks. One is the best 1000 recipes from the first 10 Bake Offs-it was my Mom’s cookbook, she gave it to me and I still use it to this day-it has the original Peanut Blossoms cookie recipe in it-I remember her making those all the time-what a treat. The second one has the best recipes from later bake-off contests-up to 1996. I love those cookbooks and all the ones I used to pick up at the check-out stand. I used to love those too. SO many great recipes.
Deanna dunham
Amazing! Loved them! I drizzeled white chocolate on them the first time. The second time I pressed them with the bottom of a glass that had a flower like design then placed a pecan in the center on melted chocolate. Yumm yumm! Thanks for sharing!!
Barbara
Deanna – great idea. Makes it almost like a turtle cookie. Thanks for letting me know!
Marthe
These look amazing, I loved them!!
Just wanted to let you know I posted about these today!
Lorraine E
I love the caramel centre, it’s no wonder these won an award, there was instant lust when I saw these!
CIA-Cooking In An Apron
These are awesome! Made them this morning and took them for to a friend (kept a few for tasting) and kinda regret giving them away…off to get another package of Rolos to make again! These are TDF!! OMG! Thanks for sharing!
Kristen
You absolutely can’t go wrong with this combination. This looks fantastic!
I have a chocolate, rolo cookie that is very similar, but not quite the same. I have a bag waiting for me to use them!
Prudy
No wonder they got an award. They look delish!
Barbara Bakes
Thanks for all the nice comments. I hope you give them a try.
Jaime -cookies definitely make me happy! A caramel brownie sounds delicious!
Katie – Sometimes I get inspired by a dish I order in a restaurant, or a fruit or vegetable at the store that looks delicious. Often it’s a recipe in a magazine that I can’t resist.
Katie
Thanks 🙂
What inspires you in the kitchen? I usually get a lot of ideas all at once but then at other times I draw a blank.
Jaime Mormann Richardson
Don’t cookies just make you happy??? These look delicious. I’ve been looking for inspiration for my Bake Sale Week on my blog. Maybe I could do some sort of caramel brownie. Mmmm. Who knows. Keep up the great work on your blog!
Deborah
I was actually just thinking of the caramel filled cookies I made awhile back, and how someone had suggested this recipe to me. I went back and looked, and it was you! This must really be a winner!!
Lisa
I can see why these won! I just put your wonderful blog in my reader.
Megan
My daughter would go nuts for these Rolo filled cookies. love the white drizzle. It makes them look so special! 🙂
Jenny
Those cookies look like a must try to me! I can see why they won a prize at the Bake-off!
~Priscilla~
oh wow those look so good! i will be trying these!
Stephanie
Wow, those look so good! I love the idea of sandwich cookies, where the filling is baked in. What a fun surprise to bite into!
Katie
YUM! Thanks for sharing. These look fabulous.
I love your blog!
HoneyB
oh these look delicious! I love the rolo in the middle! I just finished looking at my Martha Stewart Cookie book again. I am trying to decide what cookie to make next! With the weather cooling down on us some here I’m starting to think fall.