Milky Way Stuffed Sugar Cookies

My daughter requested that I make her more sugar cookies. She ate all the ones that we made and has decided they are now her favorite cookie. Her request… “heart shaped cookies with pink frosting and sprinkles”. So…. we made more sugar cookies with Sue’s amazing sugar cookie dough recipe. (Now my most favorite sugar cookie recipe.) But I wanted to make something new too. So I came up with this – Milky Way Stuffed Sugar Cookies. What do you think?

I remember seeing something like this around Christmastime and the blogger called it a pillow cookie. I believe they filled their cookies with jam or maybe chocolate chip cookie dough. (Both sound amazing!) But for the life of me I can’t remember who it was. I am sorry if you are reading this and thinking “sheesh, don’t steal my idea and not give me credit for it!)

I rolled out my sugar cookie dough (wishing I had those fancy things you put on your rollers so your dough is all the same thickness.)

I placed a Milky Way on one of the heart cookies and placed another heart shape over the top.

Smash the ends down with a fork and bake in a 350 degree over for about 10 minutes.

Of course I had to drizzle milk chocolate on them. Everything is better with milk chocolate, right?

Here’s one cut in half. Oh yeah – heaven!

I thought the next time I made these I would use Rolos. Because I love Rolos! Or maybe even raspberry jelly. Wouldn’t that be tasty?!?!


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  1. What a great idea! These look fabulous. I bet you could use all kinds of candy and fillings. Delicious!

  2. Mmmm, so many good things to stuff into a cookie! Those look yummy.

  3. These cookies were great, Erin! I loved the Milky Way center and thought the cookie dough was delicious. I bet they would be good with a Junior Mint filling too!

  4. These look awesome!

    I would love for you to link to my Virtual Valetine’s Day Party and share this great idea.

  5. Oh, I am so going to try this, Erin! Think of the possibilities! Oh boy!

  6. These look yummy! But what’s not to love about a candy and cookie marriage?
    And it wasn’t at Christmas, but Bakerella did a pillow cookie post last June using brownies. Check it out here

  7. Hi Erin
    I LOVE your blog! The creative ideas and then sharing them with your children thats really special. I love the way you make it fun for the kids:)
    I especially love your chocolate can idea “open in case of an emergency” and the ipod with ear plugs!!! Very cool:)
    I’m a follower and can not wait to try these out with my niece. She’s going to love it!
    thanks for coming by my blog: )

  8. Umm…wow?!?!? I’ll take one…or ten. I’m trying this one, like, yesterday!

  9. These look so good! Can’t get Milky Way around here, so i guess i will have to try it with another chocolate bar. I also wanted to let you know I am sending you a Stylish Blogger Award. Take a peek at my blog, you can pick up your award if you want it!

  10. What a fun idea! Getting a milky way surprise in every cookie sounds yummy!

  11. Oh yeah, we’ll be making those for sure!!!

    Lots of yummy love,
    Alex aka Ma What’s For Dinner

  12. So very cute and yummy. My 9 year old sons fav. candy is milky way, so he would LOVE these. Thanks for sharing. jen

  13. Oh goodness, a milky way in my cookie?! That’s brilliant! And your cookies look adorable – great idea for V-Day!

  14. oh my goodness. i can practically taste them from here. my kids will love these!

  15. I don’t know where I found your blog at, but thanks for sharing all the kid friendly food options. I think I could get my picky’s to eat more things if I tried some of your ideas.

  16. WOW!! These sound dangerous and the possibilties are endless!! Thanks for sharing!!

  17. Wow, another great cookie idea. Maybe I will use this recipe instead of the Stained Glass ones. Decisions, decisions.
    Was wondering if you would consider linking up to my Valentines Activities Link Up

  18. Dear Erin,
    Thank you so much for your interest in my sweet earrings.
    I can not find your email so I have to leave a post in your entry (by the way so yummy!!)
    Here you can found all the information about How to buy my handmade jewellery.

    The sweet earrings, cake portion-ice cream-croissants-donuts, cost 11€ (14.9$) and the shipment fees 6.5$
    The smaller cake portion costs 14$The payment is through Paypal but if you have Etsy account if you want I can make a reserved listing for you in my Etsy shop:

    Choose what you want from the available earrings or the donuts white or purple from This is currently available although I have to list more necklaces.
    Of course I can make more for you but every item is different because is handmade so you will never will find two identical.

    If you are still interested please send me an email at and let me know the earrings of your choice.
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  19. Yum!!! I have to try these! By the way, I saw on a baker’s blog that you can make uniform sugar cookies by using 4 paint stirring sticks (new, of course) 2 stacked together and place them apart on your counter. Put your dough down on the counter and place a piece of parchment paper on top of the sticks and dough. Roll your rolling pin over. It will give it the perfect thickness. If you like them thinner, just take away two of the paint sticks. – Karen

  20. Oh my goodness! I am SO doing this. Thanks so much! I’m new to your blog and am now following you! Great idea.

  21. Those look so yummy!

    I want to get the word out about a new site offering free giveaways every week. I would love to do an advertisement exchange with you. Check out my new site and email me if you are interested.

    Weekly Giveaway

  22. Holy cow! That is amazing! They look so good I am afraid to try them. I know I would eat them all 🙂

  23. Oh yeah! These are a keeper!! Man, they look goooood!!

  24. Yum! THat looks delicious and cute.

  25. Oh yum. These are adorably delicious. Milky Ways are my favorite right now. I am making these for myself…ok. I may give some away. Thanks.

  26. Such a great idea!
    As a child, sugar cookies were my favorite too!
    I think your kids loved the milky way cookies!
    I HAVE to make them!

  27. These look incredible. What a great idea:) My kids and hubby would go nuts for them…me too!

  28. Hop on over to the Party! Would love for you to link-up @

    The Treasurista
    Finding and Creating FUN things…

  29. STOP IT, STOP it already. How can you keep coming up with the most delicious ways to be bad. I mean seriously,,, just look at that.

    Oh man, I have to try out the sugar cookie recipe, it looks so flaky, and soft, and gooey, and yummy.

    Keep your eye out to see if you’ll be FEATURED next week, in my new sidebar feature section. 🙂

    Did you see my post about making a card for our soldiers??? You should really see if you can help out with this, I bet you could come up with something really special!!! Read about it HERE.

    THANKS so much for linking up to **AMAZE ME AUGUST**I love having you, and thanks to you, I’m getting close to my goal of having 100 link ups, YAYYY.

    Oh and PLEASE don’t forget to come enter the giveaway from LUXE BLVD, she is now offering a $20.00 store CREDIT, so you can pick ANYTHING you want, how AWESOME right?? I would be so very thankful for the support, and so would STEPH !!!!

Bella 🙂

  30. THey look awesome!

  31. Erin, those are not only cute but fun too 🙂 Just think of the possibilities..peanut butter cups, choc covered cherries…endless

  32. Oh these look good and so so pretty.

  33. Those look SUPER Yummy! What a fun treat!
    Thanks for linking up to Making It With Allie! I can’t wait to see what you have for next week!

  34. Oh this looks like fun. I’ve never made stuffed heart shaped cookies before.

  35. Wow, this is just brilliant! I just made something similar with puff pastry, peanut butter and nutella. Check it out here if you want:

  36. Yum!

    Stopping by from the Virtual Valentine’s Day party (by the way, I’m also a new blog follower. How did I not see your blog before? Cute stuff!)

  37. Whoa! Cookies and candy – you did a beautiful job with these making yours look absiolute perfection. Had seen a run of leftover Halloween candy in cookies, cakes and brownies after the holiday but many didn’t have the presentation your do. Thanks for sharing!

  38. Love it! You were featured today on my blog – Today’s Top 20! Love if you could stop by!

  39. I think I just gained weight. Gee, thanks a lot! 😉 These look wonderful. Thanks for linking up on Recipes I Can’t Wait to Try last week!

  40. These look A-mazing! What a fun way to fill your sugar cookie! Thanks soo much for sharing with the Pink Hippo Party!

  41. Hi Erin, thanks a lot for stopping by and for that lovely thought….Oh my! these cookies are indeed heaven!!! Sorry about ur grandpa….and hope ur grandma will have the strength to bear his loss.

  42. This is my VERY FIRST pin on Pinterest! I still haven’t tried them, but I haven’t been able to forget them.

  43. Oh yum, milky way is my favorite candy bar.

  44. Sugar industry, incredibly, insists that once you look at the research, no expert says that sugar leads to any disease, even obesity.

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