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Homemade chocolate and caramel Rolo cookies – perfect for anytime!

“Me like cookies!”  That’s what Cookie Monster used to say when I was a little girl.  Does he still say that?  My kids don’t watch Sesame Street, so I’m not sure.  I have heard that he does now teach that cookies are “sometimes” foods.  But probably not “sometimes I have 5 of them in a row” kind of food.  I assume anyway.

Have you ever had a Rolo cookie?  For some reason, I associate them with Christmas, but that’s kind of nonsense.  There’s nothing about Rolos that scream “CHRISTMAS!”  It’s essentially a chocolate cookie wrapped around a Rolo candy.  Once they’re cooked in the oven, the Rolo candy melts, revealing all it’s creamyness.  They’re just delicious.

Wonderful homemade Rolo chocolate cookies. The Rolo candy melts in the oven creating a creamy chocolate cookie wrapped around the yummy caramel flavors of Rolo candy. Try this recipe for a holiday treat or delicious dessert antyime. #chocolatecookie #rolocookie #cookierecipe #cookie #homemade

The mood struck for me to make these as I found a bag of Rolos that I had stashed away in the freezer.  (I also make a delicious chocolate cookie recipe with Peppermint Patties.) I had bought them on clearance after a holiday – maybe Christmas, maybe St. Patrick’s Day – I dunno.  But I had stashed them away so that I wouldn’t eat them right away.

One day I found them in there and the mood struck to make these cookies.  So I did! In a little way, I felt a little Christmas-y. Which, as I’ve said, is nonsense. These cookies are good all the time. All. The. Time.

Don’t wait for Christmas to make these cookies!

chocolate rolo cookie

Rolo Cookies

A cookie with chocolate and caramel inside
Course Dessert
Cuisine American
Keyword Rolo cookies
Prep Time 20 minutes
Total Time 20 minutes
Servings 12 servings
Author Jayme


  • 1 cup butter , softened
  • 1 cup sugar
  • 1 cup packed brown sugar
  • 2 eggs
  • 2 tsp vanilla
  • 2 ½ cups flour
  • ¾ cup unsweetened cocoa
  • 1 tsp baking soda
  • 40-48 Rolo candies


  •  Cream eggs, sugar, vanilla and butter til fluffy.
  • Mix flour, cocoa and baking soda.
  • Add dry ingredients; mix well. 
  • Chill 10-15 minutes.
  • Place 1 tablespoon dough around 1 Rolo.
  • Bake on ungreased cookie sheet for 7-10 minutes at 375 degrees.
  • Cool 2 minutes, then finish cooling on rack.

Jayme is a wife to 1 and a mother to four little boys. She tries to coupon, builds a smart stockpile, and always meal plans. While she likes to cook, she’s in the stage of life where simple is usually better – she never knows how many hands she’ll have free at dinner time! You can find her at No Regrets Living.

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