• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
Barbara Bakes™
  • Home
  • About
  • Info
  • Contact
  • Press
  • Subscribe
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
  • Breads
  • Breakfast
  • Dessert
    • Cakes
    • Cookies
    • Ice Cream
    • Pastry
    • All Desserts »
  • Main Dishes
    • Beef
    • Chicken
    • Pork
    • Pasta
    • Meatless
    • All Main Dishes »
  • Side Dishes
menu icon
go to homepage
  • Home
  • About
  • Recipes
  • Baking Tips
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
  • search icon
    Homepage link
    • Home
    • About
    • Recipes
    • Baking Tips
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
  • ×

    Home » Recipes » Dessert » Cookies

    Chocolate Caramel Rolo Cookies

    Published by Melissa on April 18, 2016 | Updated June 10, 2022 | 49 Comments

    Pin
    Share
    Tweet
    Jump to Recipe

    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.

    Featured Image for post Chocolate Caramel Rolo Cookies

    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.

    Chocolate caramel Role cookies on a brown plate

    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.

    Featured Image for post Chocolate Caramel Rolo Cookies
    Print Recipe Pin Recipe Rate this Recipe
    4.40 from 33 votes

    Chocolate Caramel Rolo Cookies

    Prep Time40 mins
    Cook Time10 mins
    Total Time50 mins
    Course: Cookies
    Servings: 2 ½ dozen
    Author: Barbara Schieving
    Prevent your screen from going to sleep

    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

    *Omit nuts and 1 tablespoon sugar if you prefer. Slightly adapted from Pillsbury Bake Off recipe
    **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.
    Pin
    Share
    Tweet
    « Sourdough Banana Bread Muffin
    Orange Creamsicle Cupcakes »
    about us

    About Melissa & Barbara

    As of June 2022 Melissa Griffiths now is the one adding recipes. So think of it as Barbara Bakes, and Melissa too! Melissa and Barbara have been blogging friends for over 10 years and when Barbara was ready to retire and spend more time with her family, Melissa took over the site. Read more...

      • Facebook
      • Instagram
      • Pinterest
      • Twitter

    Reader Interactions

    Comments

      Leave a Reply Cancel reply

      Your email address will not be published. Required fields are marked *

      Recipe Rating




    1. Nagi@RecipeTinEats

      April 18, 2016 at 6:11 pm

      I will definitely try to make this as soon as possible!

      Reply
    2. kristy

      April 18, 2016 at 5:51 pm

      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

      Reply
    3. Carol

      April 18, 2016 at 7:57 am

      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.

      Reply
    4. Deanna dunham

      November 29, 2010 at 3:45 am

      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!!

      Reply
      • Barbara

        December 07, 2010 at 6:14 am

        Deanna – great idea. Makes it almost like a turtle cookie. Thanks for letting me know!

        Reply
    5. Marthe

      July 12, 2009 at 9:01 pm

      These look amazing, I loved them!!
      Just wanted to let you know I posted about these today!

      Reply
    6. Lorraine E

      October 28, 2008 at 12:14 pm

      I love the caramel centre, it’s no wonder these won an award, there was instant lust when I saw these!

      Reply
    7. CIA-Cooking In An Apron

      September 29, 2008 at 2:26 am

      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!

      Reply
    8. Kristen

      August 30, 2008 at 8:36 pm

      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!

      Reply
    9. Prudy

      August 25, 2008 at 1:13 pm

      No wonder they got an award. They look delish!

      Reply
    10. Barbara Bakes

      August 24, 2008 at 1:31 pm

      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.

      Reply
    11. Katie

      August 24, 2008 at 4:20 am

      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.

      Reply
    12. Jaime Mormann Richardson

      August 23, 2008 at 11:55 pm

      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!

      Reply
    13. Deborah

      August 20, 2008 at 8:23 pm

      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!!

      Reply
    14. Lisa

      August 20, 2008 at 2:36 pm

      I can see why these won! I just put your wonderful blog in my reader.

      Reply
    15. Megan

      August 20, 2008 at 4:48 am

      My daughter would go nuts for these Rolo filled cookies. love the white drizzle. It makes them look so special! 🙂

      Reply
    16. Jenny

      August 20, 2008 at 4:18 am

      Those cookies look like a must try to me! I can see why they won a prize at the Bake-off!

      Reply
    17. ~Priscilla~

      August 20, 2008 at 2:57 am

      oh wow those look so good! i will be trying these!

      Reply
    18. Stephanie

      August 20, 2008 at 2:31 am

      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!

      Reply
    19. Katie

      August 20, 2008 at 1:52 am

      YUM! Thanks for sharing. These look fabulous.

      I love your blog!

      Reply
    20. HoneyB

      August 20, 2008 at 12:30 am

      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.

      Reply
    Newer Comments »

    Primary Sidebar

    Welcome!

    Melissa and Barbara smiling

    Baking made easy! Sharing fabulous recipes for cookies, cakes, pies, breads and more. Barbara Bakes (and Melissa too!) Recipes from both of our kitchens to yours.

    Learn More »

    Popular Posts

    sliced snickerdoodle bread with cinnamon chips backed by two uncut loaves

    Snickerdoodle Bread with Cinnamon Chips

    A sweet, moist, dense key lime pound cake drizzled with a tart key lime glaze. A delicious Southern twist to a traditional pound cake.

    Key Lime Pound Cake

    Featured Image for post Old Fashioned Buttermilk Donuts

    Old Fashioned Buttermilk Donuts

    6 easy cake pops on a plate made with a brownie mix, covered in chocolate and sprinkles

    Easy Brownie Cake Pops

    Footer

    ↑ back to top

    SEEN ON

    as seen on promo graphic

    SEEN ON

    as seen on promo graphic

    About

    • Home
    • About
    • Contact
    • Press

    Browse

    • Recipe Index
    • Popular
    • Baking Tips
    • Travel

    Subscribe

    • Newsletter
    • Facebook
    • Instagram
    • Pinterest

    As an Amazon affiliate, and affiliate with other businesses, I earn from qualifying purchases.

    Copyright © 2022 barbarabakes.com. All rights reserved. DISCLOSURE - PRIVACY POLICY.