Caramel Filled Chocolate Cookies


Caramel Filled Chocolate Cookies are rich, chewy chocolate cookies, oozing with melty caramel.


Mark your calendars, it’s December 11th and we finally got our first snow of the year!


I opened the blinds around 7am and there was already a 1/4 inch of the fluffy stuff covering the ground.


Unfortunately it was preceded by rain that fell in the middle of the night, which turned into a thick sheet of ice under the snow.


On the way to the grocery store this morning I witnessed an SUV come this. close. to wrapping itself around a light pole when it skidded on some hidden ice coming down a hill. Eek!


We’ve got a blizzard warning in effect until tomorrow morning,


which has left both Ben and I feeling a little like this:


(That’s his “You’ve got to be kidding me” face. Haunting.) While we’re both ready for a little snow to help us get in the holiday spirit, a blizzard is not quite what we had in mind!


The only answer was to hunker down this afternoon, away from the blowing wind and snow, and bake cookies!


We had a healthy debate regarding what to bake. I was craving Peanut Butter Cookies while Ben gave a pretty convincing argument for mixing up a big batch of Ultimate Cookies. In the end, though, we turned to the recipe binder.


Ohhh the recipe binder!


You see, when I got into cooking while living in Minneapolis after college, I became obsessed with printing out recipes and storing them in this very binder. Organizing them by category, of course.


For whatever reason I never got around to making half of them, but there’s one cookie recipe inside that I made dozens of times.


The cookie that blows all other cookies out of the water…


Caramel Filled Chocolate Cookies!!!!!


We’re talking rich, chocolately cookies oozing with gooey, melty caramel.




It starts with a pretty standard chocolate cookie recipe.

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You’ve got your butter, sugars, egg & vanilla laced with cocoa powder.


Chocolate cookies = check. But where’s the caramel part of the caramel filled chocolate cookies?!


Bingo! Rolos!!!


It’s seriously ingenious.


All you do is scoop out some dough,


and stuff a rolo in the middle!

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Roll the ball around in some granulated sugar to make it sparkle,



Then bake to warm, melty perfection.


I guarantee these cookies will be the hit of ANY party, or the star of your own personal party, aka your midnight snack. Don’t forget the almond milk….


Lots of it!


Caramel Filled Chocolate Cookies

Makes 24 cookies


Caramel Filled Chocolate Cookies are rich, chewy chocolate cookies, oozing with melty caramel — so sinful!


  • 1/2 cup butter
  • 1/2 cup granulated sugar
  • 1/2 cup brown sugar
  • 1 egg
  • 1 teaspoon vanilla
  • 1-1/4 cup flour
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/4 cup + 2 Tablespoons cocoa powder
  • 24 rolos
  • 1/4 cup granulated sugar


  1. Pre-heat oven to 375 degrees. Cream butter and sugars until fluffy. Add egg and vanilla then mix until combined.
  2. In a separate bowl mix flour, baking soda, salt & cocoa powder. Add dry ingredients to wet ingredients in three batches, mixing well between each batch. Chill dough for 1 hour in the fridge or 20-30 minutes in the freezer.
  3. Scoop out ~1 Tablespoon dough and wrap it around a Rolo candy. Roll dough in sugar and place on a baking sheet. Bake for 8 minutes, rotating pan half way through.

This recipe is courtesy of Iowa Girl Eats,


While my cookies were baking I was also working on another yummy project, using yeast, which is now rising on the warm cook top. Who am I?


First Pumpkin Cinnamon Rolls, then regular Cinnamon Rolls, and now this?! I’m crossing my fingers that all goes well and I can share with you the delectable, savory treat I’m workin’ on tomorrow. Until then…I’ve got a mess to clean up!


Have a great night!


What’s your favorite cookie to bake up on a chilly, winter day?

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  1. Gah, those look delicious! I used to do some major damage with rolos back in the day…

    My favorite cookie has always been white chocolate macadamia, but I made some pretty mean mint chocolate chunk ones today that very well may be the new favorite!

  2. I wonder if a vegan version of this would work and look as delicious!

  3. VeggieGirl 12.11.2010

    I usually like baking gingerbread man cookies, but I want THOSE that you just made! :D

  4. Heather 12.11.2010

    Those cookies look AMAZING. And just in time for my cookie exchange this week. WOOT!

  5. Melanie 12.11.2010

    I love making molasses ginger cookies – they make the whole house smell like Christmas!

  6. delia 12.11.2010

    I just whipped up a batch of chocolate cool whip cookies. They’re so yummy :)


  7. Renee 12.11.2010

    Northern Iowa has had snow… How did you manage to not get any til today? I’m jealous! lol.. but yes, now its blizzardy up here … I wish I would have gotten my bake on. And now that I see those cookies, I’m adding that baby to this years list.

  8. my friends’ roommate in college would make rolo cookies all the time! haven’t had them in years… so fun :)

    and we’ve already had about 4-5 inches of snow in the past couple weeks in indiana. yuck :(

  9. Elizabeth 12.11.2010

    Oh, I have got to try that recipe over Christmas. They look dangerously delicious!

  10. Those cookies look so gooey! I had similar cookies at a party…made with caramel cubes and chocolate chips. I. Could. Not. Stop. Eating. Them! I’ll have to try out your recipe soon.

    Ben’s face is priceless. I hope the snow isn’t too outrageous.

  11. Rachel 12.11.2010

    Those look a lot tastier than the hazelnut biscotti I made this afternoon! That being said, my favorite cookie to make is a peanut butter chocolate chip cookie. Yum!

  12. Dee 12.11.2010

    Oh my gosh! I just showed this recipe to my husband and his jaw literally dropped! :)

  13. Jessica H. 12.11.2010

    We are northeast of you and have received a lot more snow! We are supposed to get 6 more inches throughout the night :(

    I showed my husband those cookies and he asked if he should go down to his parent’s house to grab some rolos so I can make them. The roads are too bad for us to travel to the grocery store. I think it’s a hint he wants me to make them :)

  14. Hannah 12.11.2010

    I have been making these for years too! That reminds me that I must go make/eat them now.

  15. girliefriend 12.11.2010


    Is Ben growing his winter coat or is that just weekend scruff? He is priceless.

  16. maggie 12.11.2010

    mmm…i am definitely trying those! i wish i had all the ingredients so i could bake them now!
    my mother-in-law bakes something similar. she uses peanut butter cookies and puts mini snickers inside. they are AWESOME:)

  17. 1) Ben’s face is HIL-arious. It captures his mood perfectly. Ha.

    2) Oh baby those look good. I’ll have to try them this holiday season.

    and 3) My favorite cookie to bake on a cold, winter day is probably ginger. I have an awesome recipe for soft, chewy ginger cookies that’s just to die for. Fresh out of the oven, they’re perfect with a tall glass of milk.

    I can’t imagine many things that are better than snuggling up with a cozy blanket in your pajamas on a cold, winter day and nibbling on a plateful of warm cookies with ice cold milk. Mmmmmmm. Fantastic!

  18. Lori 12.11.2010

    I definitely want to make those! I am in the middle of the blizzard up here in MN and made zucchini muffins today. There is something about cold, snowy days and baking. Thanks for sharing your recipe!


  19. Sarah 12.11.2010

    Those cookies look delicious! I love the caramel in them!

  20. Izzy 12.11.2010

    That TOTALLY blew my mind! I thought this was gonna be some complicated “Caramilk-secret” type recipe then BAM! Obviously delicious and ingenius! Dumb question – do you use the mini Rolos or the regular sized ones? (Clearly my sense of perception and size if OFF because I couldn’t figure it out! :P)

    Totally borrowing this recipe!


  21. Lo 12.11.2010

    Those cookies look amazing!! Definitely the next kind I will try! Meanwhile, I am growing increasingly jealous of the weather that seems to be prevalent in the majority of the American blogs I read… up here in the coldest capital city in the world (no kidding, look it up! :)), Winnipeg, Canada, we have had over 30 cm of snow in just a few days… around the end of November, and that was a late snowfall! It was also -32C (-26 F) today! Unfortunately for us, life still goes on. I don’t think we’ve ever had a snow day! But it is just another excuse to bake! Have a good weekend!

  22. Susie 12.11.2010

    You can have some of our snow! 15 inches is way too much.

    I have not been able to find rolos at Target the last two times I have been there! UGH. I need to make those…as soon as I can get out of my house!

  23. Shelley 12.11.2010

    Seriously I’m dying right now. I want those cookies! But I’m pretty sure there’s nothing in the world that could convince my hubby to go out and buy Rolos. Bummer. We’re planning on trying a new sugar cookie recipe with the kiddos tomorrow so I guess that will have to do!

  24. BroccoliHut 12.11.2010

    Wow, those look delicious!
    I love to make the “You Got Peanut Butter in my Chocolate” Cookies from Eat, Drink, and Be Vegan–they taste like peanut butter Oreos!

  25. Kristin from MN 12.11.2010

    Those look aMaZiNg! I need to make those I think! Btw I used rolos to make pretzel turtles today. We too are in a blizzard here in MN so my son and I baked! We also made TJ’s sugar cookie kit, russian tea cakes, and oreo truffles. My son made some JELLO oreo pudding all by himself! And for supper we had Tastefully Simple’s chicken & dumpling soup and it was TDF! HIGHLY recommended! The picky hubs even gave it his approval! :)

  26. I need to do that with some of the recipes I have saved on my computer. My bookmarks are OUT OF CONTROL!

  27. Dream Mom 12.11.2010

    Oh, those look good. It’s funny how the snow brings on cookies! I think my favorite cookie this year seems to be these peanut butter cookies. I got the recipe many years ago from a woman and they are wonderful. Same idea as yours-you roll them in granulated sugar before baking them. They are delicious!

    Question-How on earth do you make all of those wonderful cookies and not eat them? You and Ben must have some good willpower, lol!

  28. krista 12.12.2010

    I made those cookies over my summer break, but with just caramel squares. They, um, didn’t turn out too hot; definitely going to try your recipe! :)

    I’m so excited to hopefully get home to snow up in the northeast– can’t wait to get ‘stuck’ inside and bake!

  29. Ashley M. 12.12.2010

    That recipe looks fantastic! I am def. in the baking mood after the snow we got. Yesterday, I made the no bake pb cookies you had linked to on twitter. Fantastic! Keep the cookie recipes coming!

  30. ultimate cookie doesn’t even begin to describe this…i don’t know if they would even make it to a party in my house!

  31. Mimi 12.12.2010

    Yum! Those sound amazing!
    We just got our first snow here (in Kansas), which is always so magical!

  32. I think my favorite cookie to bake on a cold day are Peanut Butter Treat Cookies. So easy, 4 ingredients. One of those, why didn’t I think of that!?!?! recipes!

  33. lauramich 12.12.2010

    Those cookies look tasty! I may have to try those for my own holiday baking. I don’t have any Rolos in the house, but I do have plain old caramels; I bet those would work!

    I, too, love nothing more than cranking up the oven on a cold, snowy day. However, I’m more likely to be whipping up some pumpkin bread, or a batch of granola. If I am making cookies, they’re probably oatmeal cinnamon chip cookies or bars, minus the raisins (which Teh Husband deplores in baked goods). The Hershey’s cinnamon chips can be tricky to find, but they’re more widely available during the holidays, so I’ve been stocking up. :D

  34. Machelle 12.12.2010

    Everything Cookies-which makes a huge batch & are a bit pricey to make cuz as the title says….they have everything in them! All the normal batter ingredients plus oats, rice crispies cereal, coconut, mini choco chips. They are darn good tho! I also like to make pumpkin bread from a mix bought at the store & toss in a handfull of mini choco chips……delish! And could not be easier!

  35. Eve P 12.12.2010

    Peanut Butter cookie with a Mini Snickers in the middle. (Made like the recipe you just shared.)

  36. Tessa 12.12.2010

    My mom has made these for Christmas for as long as I can remember too. They are awesome! I love your photo of the cookie split in half with the caramel oozing out… yum!

  37. Mic Jones 12.12.2010

    I am curious to know what type of lens you use for your food shots? Do you use a macro? Keep up the good work!

    • Iowa Girl Eats 12.14.2010

      I use the one that came with the camera (NikonD3000). I think it’s a 55mm?!

  38. Danielle 12.12.2010

    Those cookies look so good! I think I may have to bake them this week!

    Thanks for sharing the recipe :)

  39. sandy 12.13.2010

    Those cookies look SO GOOD and I love caramel! Does the caramel stay gooey even after the cookies have cooled?

    • Iowa Girl Eats 12.13.2010

      It’s about as gooey as it is when it’s in the center of the rolo. A quick 10 sec spin in the microwave will help though! :D

  40. […] Caramel-Filled Chocolate Cookies, a la Iowa Girl Eats […]

  41. I baked all day Saturday, too, including a huge batch of Ultimate cookies. We were scooping them out and my daughter kept asking “How many cookies will this make?” (I was rotating three different cookie sheets and it still took hours!) I showed her your posting with the oh-so-accurate “This makes a TON of cookies!” She was definitely convinced. And they were delicious, if not a little crispier than I like my cookies. Yummy, nonetheless, thank you!

  42. Ffion 12.17.2010

    We got some snow today too, and I have to say I was not impressed! I made it into work, but we were very understaffed, which makes it ten times harder for the people there! I am hoping to have a snow day tomorrow, so that I an bake like you did. Those cookies look amazing!

  43. Katie 12.19.2010

    Kristin, I just had to tell you, I made a double batch of these to bring to work & to a holiday potluck, and they were a HUGE hit with everyone! They are so easy to make, too. Everyone was asking for the recipe.

  44. Shel 12.19.2010

    I’m making these right now for our family Christmas later in the week. I have the Christmas music blaring. If only my house wasn’t the staging area for a steel cage match between my two kiddos!

  45. Malinda 12.21.2010

    These cookies are soooo good and suprisingly easy! Thanks for posting! My new favorite cookie for sure! Just made a second batch tonight!

  46. Sarah 12.22.2010

    A tip: the first time I made these, they were great! But, for some reason, they got a little too “chewy.” I made these a second time around last night and put half a box of instant vanilla pudding mix in the dry ingredients and, I must say, I feel it helped quite a bit! :)

  47. lauren 02.06.2011

    Well I couldn’t find rolos so I am trying w. the caramel hershey kisses. Fingers are crossed it is as delish as yours look! :) Happy superbowl everyone!

  48. […] me present to you Kristin’s Caramel-Filled Chocolate Cookies.  If I child had one of these cookies and I didn’t, I might take it from them.  Kidding.  […]

  49. […] with the in-laws), I needed a new dessert idea. After searching the internet, I decided to go with Iowa Girl Eats Carmel filled chocolate cookies. I didn’t post the recipe because IGE does a great job walking through it, but if these […]

  50. Stephanie D. 11.02.2011

    Just found this recipe and oh my goodness – just fabulous! I added pecans to the batter and little finely chopped pecans to the sugar on the top AND then drizzled with white chocolate. YUMMY! I doubled the recipe & made about 48 cookies and the folks in my office scarfed them down! Thanks for sharing!!

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