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Festive, easy, and cute, Roly Poly Pumpkin Cookies with Cinnamon Maple Frosting. Simple vanilla sugar cookies shaped into the cutest, fattest little pumpkins, made effortlessly by shaping the dough into ovals and balls. Frost with a deliciously sweet cinnamon frosting and you’ll have yourself the most perfect Halloween and Thanksgiving cookie. Fun to bake, delicious to eat, these pumpkin-shaped cookies also make for a great homemade gift!

Roly Poly Pumpkin Cookies | halfbakedharvest.com

So maybe these don’t look exactly like pumpkins, but they’re close enough. We’re about to enter into the time of year I love the most. Halloween is Sunday and that means the holidays are basically here.

Since I’m never one to forget about Halloween (it’s actually my second favorite holiday), I really wanted to create a sweet cookie that would be cute for both Halloween and Thanksgiving.

I came up with the idea for these cookies while hiking, then kept thinking on them the rest of the day. I tried to figure out how to make these easy for you guys…and here we are!

I’m so excited to share these.

Do you all remember my Holly Jolly Santa cookies? Well, they’re one of my all-time favorite holiday cookies. I love them and their cuteness so much. I thought how could I take that cookie and turn it into a cookie fit for Halloween as well as Thanksgiving?

Ah, make fat, roly poly style pumpkins! They’re not perfect, but what I love most about them is that they’re unique, fun to make, and so delicious. Of course.

Roly Poly Pumpkin Cookies | halfbakedharvest.com

(the pieces)

Here’s how you make these pumpkin shaped cookies

Start with the dough. I used my favorite sugar cookie dough that’s heavy on the butter…and vanilla. I died three-fourths of the dough orange, using food coloring, and kept the other half of the dough plain. If you can find a great natural orange food die, I would highly recommend using that. Sadly I’ve yet to find one that works well. If anyone has found one they use and love, please let me know!

 

Once you’ve died the dough, simply roll it into balls. Then take the orange balls and form them into long ovals – kind of like an eggplant – with one end a little larger than the other. If you look through the photos you will most likely understand the process much better. You need five orange dough balls and 1 white dough ball to make one pumpkin.

Roly Poly Pumpkin Cookies | halfbakedharvest.com

(before adding the stem)

Attaching the pieces

This is the step that you might think will be tricky, but it’s actually so easy. To make each pumpkin, just gently push the orange pieces into a circular pattern. Then, grab that plain dough pall and position it at the top of the pumpkin, shaping it into a stem. Once again, use the photos as guides. Nothing needs to be shaped perfectly or lined up just right. As long as you have a rough half-circle formed, the cookies will bake up like adorable fat pumpkins.

Roly Poly Pumpkin Cookies | halfbakedharvest.com

(use a pumpkin cookie cutter to help better shape the cookies)

Promise.

Once you have your pumpkins formed, I like to freeze them a few minutes to help them hold their shape. Then bake – that’s it!

To me, this is easier than cutting out shapes. And I think they are way cuter, not to mention a little more unique.

Roly Poly Pumpkin Cookies | halfbakedharvest.com

(ready to bake)

Decorating is easy.

I used a sweet cinnamon-spiced brown butter frosting to add a layer of warming flavor to each cookie. You can decorate them any way you’d like. I just did simple swirls and a light dusting of cinnamon sugar.

My one tip? Keep a small bowl of the frosting aside for adding to each cookie while eating. I didn’t use a ton of frosting for decorating, so having a little on the side was so good.

Roly Poly Pumpkin Cookies | halfbakedharvest.com

Hoping these cookies excite you guys! They’re honestly so much fun to make. And I love that they’d be equally great for Halloween this weekend and Thanksgiving in a few weeks!

Roly Poly Pumpkin Cookies | halfbakedharvest.com

Looking for other easy fall cookies?? Here are my favorites: 

Chewy Brown Sugar Maple Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Pecan Pie Cookies with Butter Pecan Frosting

Browned Butter Pecan Chocolate Chip Cookies

Chai Spiced Maple Sugar Cookies

Lastly, if you make these Roly Poly Pumpkin Cookies, be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Roly Poly Pumpkin Cookies with Cinnamon Maple Frosting

Prep Time 45 minutes
Cook Time 15 minutes
Total Time 1 hour
Servings: 16 pumpkin cookies
Calories Per Serving: 197 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.

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Ingredients

Frosting

Instructions

  • 1. Preheat the oven to 350°. Line 2 baking sheets with parchment paper.
    2. In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes. Add the egg and beat until combined. Add the flour, and salt, beat until combined and the dough begins to form a ball.
    3. Remove 1/2 cup of the dough and set aside. With the remaining dough, add in 1 teaspoon orange food coloring, adding more if needed for better color. Keep in mind that the color will darken over time. If the dough is feeling wet, add 2-3 tablespoons flour.
    4. From the orange cookie dough, make 5 (1 teaspoon size) balls. From the plain cookie dough, make 1 (1/2 teaspoon size) ball.
    5. On the prepared baking sheet, roll the orange balls into rounded ovals, kind of the shape of an eggplant, fatter at the bottom and skinnier up on top. Arrange the pieces side by side, making a rough pumpkin shape. Next, attach the plain dough ball at the top, shaping the dough upward as a stem. Repeat with remaining dough. Arrange the cookies 2 inches apart on the baking sheet. If desired, you can take a similar size pumpkin cookie cutter and fit your cookie inside the cutter to help form a better pumpkin shape (see above photos).
    6. Freeze 10 minutes. Bake the pumpkins for 12-15 minutes, until lightly golden.
    7. To make the frosting. Melt together the butter and maple syrup in a small pot over medium heat. Remove from the heat and whisk in the powdered sugar and cinnamon.
    8. To decorate. Transfer the frosting to a piping bag fitted with a small tip. Or, take a ziplock bag and snip a very small portion of the corner off the bag. Decorate as desired.

Notes

Orange Food Coloring: To make orange food coloring, mix 25 drops of red food coloring and 8 drops yellow food coloring. 
Storing: the frosting will set up, but it’s best to store these cookies in a single layer in an airtight container. If using these cookies to fill a cookie box, place a piece of wax or parchment paper between each cookie to help protect them, then carefully stack the cookies, or line them up side by side. 
Freezing: unfrosted cookies can be frozen for up to 3 months. Thaw, then decorate as directed. 
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Roly Poly Pumpkin Cookies | halfbakedharvest.com

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Comments

  1. 5 stars
    These were delicious and super simple to make (while still looking fancy). Your recipes never fail! I was even able to modify for my daughter’s egg allergy (using a flax egg) and they held up great!

  2. 5 stars
    These were a big hit at Thanksgiving. They turned out so cute! We had extra frosting, so we saved it and used it to top homemade waffles for breakfast. Delicious!

  3. 5 stars
    Definitely easier than rolling/cutting, and the 10 min in the freezer is a must to keep the shape. Super cute and tasty Fall treat.

    1. Hey Breanne,
      I would say it’s about 3 inches. I hope you love the recipe, please let me know if you have any other questions! xTieghan

  4. 4 stars
    I made these today as a test run for Thanksgiving. I didn’t use food coloring since they were just a test run. I loved the way they turned out, they looked great and tasted great. I did have an issue with the dough, it didn’t ball up in the mixer, it was a little sticky, so I added more flour 1 Tbs at a time, then I tasted it & thought it needed a bit more sugar, so I added some. Since the dough didn’t ball up, I decided to use a little flour on my hands to help roll the balls into their eggplant shape and that worked great. They were a great hit at home. I will make them for thanksgiving and color them and ice them. Thank you for the recipe.

    1. Hey Stephanie,
      I am thrilled that you enjoyed this recipe, thanks a lot for giving it a try. Thanks for sharing what worked well for you. I hope you have an amazing week! xTieghan

  5. Hi! Im so excited to make these cookies! But I was wanted to make sure there is NO baking powder or baking soda in the cookie dough? Thanks!

  6. 3 stars
    While I love the flavor of the cookies, even though we squished the individual pieces together into the pumpkin shape, after baking, the pieces would not stick together and the pumpkins fell apart. The dough was very greasy and I think that contributed to the issue. The frosting was great and everything tasted great but I couldn’t give them as gifts as I had planned. So I was a little bummed. If anybody has any suggestions for how to solve that problem, I would love it because I would love to make these and have them turn out as cute as the photographs!

    1. Hi Patricia! I’m so sorry this recipe didn’t turn out the way you hoped! Is there anything you did differently during this recipe? Let me know how I can help! xTieghan

  7. 4 stars
    These were so fun to make for a halloween party! The icing makes these taste just like a Frosted Brown Sugar Pop-Tart. (yum) The extra cinnamon and sugar on top gave these a special pop. Can’t wait to make the ‘santa’ version this Christmas!

  8. Not sure what happened in the transition from web to printing, but, when I printed the recipe, it said 12 TBS of maple syrup.

    I followed the printed recipe and realized something must not have been correct so I looked on the blog and it’s 2TBS. Big difference!

    Hopefully, the glitch can get fixed before too many others make the same mistake 🙂

    The cookies are cooling and super adorable. Looking forward to icing them soon.

    1. Hi Sheila! I am so sorry about that, that was my mistake! Glad you didn’t make the icing yet, I hope you enjoy these! xTieghan

      1. Thanks for fixing it! I actually did make the icing with the 12 TBS and then checked the blog and saw the mistake. I’m not tossing it though – I’ll just have some really sweet syrup for pancakes haha!

        Love the balance of the cookies and icing! The cookies are not too sweet at all and the combination of cinnamon with the maple & butter is just plain yummy!

        Glad you got it fixed! Thanks for all you do! Happy Halloween!

  9. So cute and they tasted good too!! My icing was a little liquid but extra icing sugar fixed that problem and I’m not sorry I have excess icing!!! Your holiday recipes are the best anywhere to be found – Thankyou for sharing this recipe.😊

    1. Hi there! I’m so sorry about that, I accidentally wrote 12 tablespoons instead of 2 in the recipe, which is probably why it turned out liquid-y! My apologies! xTieghan

  10. The Roly Poly pumpkin cookies are darling — and I can’t wait to make them tomorrow with my granddaughters. You’re more than welcome to delete this comment — but just a heads up — the cookies aren’t DIED — there DYED!! I think you misspelled that word a couple times in the recipe. LOVE your recipes and website — it’s the first place I turn to when looking for something new and delicious to make!

    1. Trisha, you certainly are correct about the spelling of the word “died” as being “dyed”, but it could have been intended as a pun for Halloween? And spell check isn’t always the friend that we think it should be…as in your use of “there” instead of “the’re”. I am sure spell check “corrected” for you. 😉

        1. OH MY GOSH!!! We’re NOT in a spelling Bee ( or did I spel that wrong) 😂 we’re just here trying to get a pumpkin cookie recipe.
          Seriously 😳!!!???

  11. These are absolutely adorable. I follow your blog every morning reading it with my cup of coffee in hand. You are a part of my daily routine.

    1. 5 stars
      Absolutely agree!! Wish it wasn’t too late to make them & send them out to Florida to my step-daughter. She loves Halloween 🎃