Rolo Stuffed Chocolate Chip Cookies – An Indulgent Snack

by Erin, The $5 Dinner Mom on March 23, 2011

rolo stuffed cookies 3

I’ve just got to get this out of my system.

Ever since I saw these Oreo Stuffed Chocolate Chip Cookies over at Picky Palate, I’ve been wanting to try something similar. I have a little thing for chocolate chip cookies. And by little, I mean big. And by big, I mean huge. And by huge, I mean…

You get the picture.

After making these, I’m really not sure that chocolate chip cookies will ever be the same again. I am not sure I’ll ever be able to make unstuffed cookies again!

The key with these…

You have to let them cool to just the right temperature.  Still a bit warm, but cool enough for the caramel to have started to harden.  But only just a little bit.

And if you get it at just the right time, you take a bite…and as you pull the cookie away, a long string of caramel forms and you have to catch it!

It’s a moment of ooey, gooey stuffed cookie perfection.

I sure hope you can recreate that moment!

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Rolo Stuffed Chocolate Chip Cookies

Inspired by Oreo Stuffed Chocolate Chip Cookies

Ingredients

  • 2 1/2 cups flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 cup butter or margarine
  • 3/4 cup sugar
  • 3/4 cup brown sugar
  • 1 tsp vanilla
  • 2 eggs
  • 2 cups chocolate chips
  • Enough Rolos for each cookie, about 18

Directions

  • In a mixing bowl, whisk together the flour, baking soda and salt.
  • In a stand mixer or mixing bowl, beat together the butter/margarine and the 2 sugars. Add in the vanilla. Beat in the eggs, 1 at a time, until smooth. Scrape down the sides if necessary.
  • Add the dry ingredients and mix on low speed, until batter forms.
  • Fold in the chocolate chips.
  • Flatten the Rolos, using a potato masher, or the bottom of a measuring cup.
  • Form the cookies by placing dough on top and on bottom of the flattened Rolos. Place on cookie sheet, or Silpat baking mat, and bake at 350 for 9-11 minutes, or until begin to golden.
  • Let cool slightly before serving. Makes 18-24, depending on how much dough you use for each cookie.

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{ 15 comments… read them below or add one }

Tammy March 23, 2011 at 2:51 pm

Thanks! Just what I needed on a day I’m on a clear-liquids diet! =) Hee hee ~ after my procedure tomorrow, though ~ these are on the “to do list” ~ they look fabulous!!! =)

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Linda March 23, 2011 at 3:23 pm

Oh my….. these look just amazing ! thanks Erin for the lovely pictures. I will have to try this, as long as I don’t eat all the Rolo’s before.

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Tammy Lou March 23, 2011 at 5:17 pm

This sounds like a great idea! I love rolos but when they’re tough to chew when they’re cold (I always worry that I will lose a crown) so this would be perfect!

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Angela G March 23, 2011 at 7:19 pm

OMG. Too yummy looking. And to think, I was ahem I mean I am going off chocolate for two weeks. Saved by the fact that I have NO Rolos in my house. Phew.

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Laurie March 23, 2011 at 8:42 pm

I gave up chocolate (and all sweets!) for Lent. I am soooooooo planning to make these to enjoy the day after Easter . . . Easter Day is dedicated to Cadbury Eggs alone!

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TheGourmetCoffeeGuy March 23, 2011 at 11:24 pm

A great recipe for a day of delicious self-indulgence. Very nice photo.

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Food on the Table March 23, 2011 at 11:39 pm

Ooh! Reminds me of a recipe I saw on a blog a few days ago. Get this: cake ball-stuffed chocolate chip cookies. Basically, any sort of dessert-stuffed dessert is a winner in my book.

Thanks for sharing this!

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Tricia H March 24, 2011 at 12:40 pm

Oh my!!!!

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Crystal's Cozy Kitchen March 24, 2011 at 1:38 pm

I made cookies stuffed with rolos as well, they were absolutely delicious! However, I did not flatten them and they turned out great.

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The Marketeer March 28, 2011 at 4:55 pm

Those look good enough to sell at a markup! …Or eat.

Cheers! The Marketeer.

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Audrey April 3, 2011 at 2:22 pm

These cookies look amazing! I couldn’t wait to try them, but had no Rolo…so, I dug around to find something else to stuff them with. I had some chocolate cheesecake so I stuffed the cookies with about 1/2 tsp of that instead. Awesome!!!! Thank you for the inspiration and for the delicious recipe!

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Cathy Cordero December 30, 2011 at 11:02 pm

So how DO you get your cookies to not spread all over the place?? I tried making these tonight, followed your directions exactly and they spread and then fell apart because they were so thin even after cooling for a bit.

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Erin Motz February 8, 2012 at 9:41 pm

I just discovered your blog and I love your ideas. :-) I have to say, WOW! These look incredible! Bookmarking this for later… and by “later” I mean in like 15 minutes, haha.

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Lisa Moore March 1, 2012 at 12:07 pm

At a place called Truffle Berries in town they have these BUT they’ve had Ruffles potato chips added to them and are called PMS Cookies. Oh, they are awesome!

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Stephanie July 7, 2012 at 8:56 am

Just now discovering your blog — so many great new recipes to try out. Rolo cookies are a holiday staple in my family. We make them in a chocolate cookie, dusted with chopped pecans and sugar. Delish. You can also just roll the unflattened Rolo into the cookie dough ball and they’ll turn out great. I gotta give these chocolate chip cookie ones a try some time soon!

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