Chocolate Caramel Rolo Cookies

by Barbara on August 19, 2008

This is a family favorite cookie recipe that we have been making for years. It was a $2,000 winner in the 1990 Bake-off. How can you go wrong with the combination of chocolate and caramel. These cookies are better if slightly underbaked. I’m not a nut lover, and omit the nuts.

Chocolate Caramel Rolo Cookies

2 1/2 cups flour Pillsbury BEST® All Purpose or Unbleached Flour
3/4 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
48 Rolo® Chewy Caramels in Milk Chocolate, unwrapped (from 13-oz. pkg.)
1 tablespoon sugar
4 oz. vanilla-flavored candy coating, if desired

DIRECTIONS
1. In medium bowl, combine flour, cocoa and baking soda; mix well.
2. In 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 1/2 cup of the pecans. If necessary, cover with plastic wrap; refrigerate 30 minutes for easier handling.
3. Heat oven to 375°F. For each cookie, with floured hands, shape about 1 tablespoon dough around 1 caramel candy, covering completely.
4. In small bowl, combine remaining 1/2 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.
5. 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.
6. Melt candy coating in small saucepan over low heat, stirring constantly until smooth. Drizzle over cookies.

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{ 19 comments… read them below or add one }

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.

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Katie August 20, 2008 at 1:52 am

YUM! Thanks for sharing. These look fabulous.

I love your blog!

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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!

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~Priscilla~ August 20, 2008 at 2:57 am

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

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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!

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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! :)

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Lisa August 20, 2008 at 2:36 pm

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

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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!!

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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!

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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.

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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.

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Prudy August 25, 2008 at 1:13 pm

No wonder they got an award. They look delish!

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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!

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Annarasa September 3, 2008 at 5:25 pm

Gosh, these look divine!!

Apu

http://annarasaessenceoffood.blogspot.com/

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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!

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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!

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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!

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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!!

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Barbara December 7, 2010 at 6:14 am

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

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