Pumpkin Cinnamon Roll Cookies

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Pumpkin Cinnamon Roll Cookie dipped into a glass of milk

Cinnamon rolls and I kinda have a thing. You see, we’ve practically been lovers since the 3rd grade when I discovered they were the one thing the lunch ladies at my school made from scratch that actually tasted like food.

Chili and cinnamon roll days were a special occasion and only came around once every few weeks in the winter months. This meant every fourth Friday people went into an all-out flurry rushing to the cafeteria to claim their sticky prize. Little did they know I’d sidled them and was always first in line, wide-eyed gripping my tray with a silly grin on my face, waving my finger at the biggest cinnamon roll in the bunch chirping “Ooh ooh, mine mine,” at the lunch ladies. They surely hated my 10-year-old self, tragically crooked teeth and all.

What ensued next was practically material for “50 Shades of Grey.” As I sat perched on the brown plastic benches in our cafeteria I stole delicate bites of my cinnamon roll between sinfully large spoonfuls of chili and anticipated that last ooey-gooey center bite – a climax and tragic ending all in one. Once the experience drew to a close it was cold lunch city provided by mom until the next chili and cinnamon roll day came around.

Cutting board with rolled out dough and filling for our Pumpkin Cinnamon Roll Cookies recipe

Pumpkin Cinnamon Roll Cookie resting on the rim of a glass of milk

I’ve tried to make cinnamon rolls from scratch before, but without my mom by my side gently instructing me at every tur they always turn out like hockey pucks – nowhere near worthy of being enveloped in creamy frosting and consumed while cuddled up in a cozy chair with a hot cup of tea. Not even close.

Plate with two Pumpkin Cinnamon Roll Cookies drizzled with icing

So my solution in the meantime? Cinnamon roll cookies. PUMPKIN cinnamon roll cookies. You know, because it’s fall and whatnot.

Batch of Pumpkin Cinnamon Roll Cookies on a cooling rack

Whisking together icing ingredients for Pumpkin Cinnamon Roll Cookies

This caramel glaze is my mom’s super secret recipe that she would share with anyone who asks. I called her the night before I baked my cookies to copy down the instructions and once more when I was in the process of making it. I wanted to make sure it was just right; can’t bring cinnamon roll disgrace to the family name, after all.

Batch of Pumpkin Cinnamon Roll Cookies drizzled with homemade icing

Hmm, based on the texture, caramel flavor and how it practically slid off my whisk onto my cookies, I’d say I nailed it.

Plate of two Pumpkin Cinnamon Roll Cookies drizzled with icing

Close up shot of Pumpkin Cinnamon Roll Cookies on a cooling rack

Wondering what they taste like? Imagine a delicate sugar cookie with a gooey pumpkin butter-brown sugar center and a melt-in-your mouth caramel glaze. One cookie in and you’ll already be dreaming about your next two.

These aren’t your delicate tea time, laugh with your mouth closed and legs crossed type of cookie. They’re more of a full fat chocolate milk from the can “eat like a trucker while grunting ‘yeeeee haw'” type of cookie. Get the picture? Yeah…good.

Plate and cooling rack with a batch of our Pumpkin Cinnamon Roll Cookies recipe

Dipping a Pumpkin Cinnamon Roll Cookie into a glass of milk

Pumpkin Cinnamon Roll Cookies

Delicate sugar cookies prepared in one bowl with a pumpkin butter-brown sugar center and topped with a rich caramel glaze.
Author Minimalist Baker
Print
Dipping a Pumpkin Cinnamon Roll Cookie into a glass of dairy-free milk
4.86 from 14 votes
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings 24 (cookies)
Course Dessert
Cuisine Vegetarian
Freezer Friendly 1 Month (cookies only)
Does it keep? 2-3 Days

Ingredients

DOUGH

  • 1 stick butter (slightly softened)
  • 1/2 cup sugar
  • 1/2 cup brown sugar
  • 1 large egg
  • 2 cups all-purpose flour
  • 1 cup whole-wheat pastry flour
  • 2 tsp baking powder
  • 1/2 cup milk
  • 1 tsp vanilla extract
  • 1/4 tsp salt
  • 1 tsp cinnamon
  • 4 Tbsp pumpkin butter

FILLING

  • 1 tsp each cinnamon and pumpkin pie spice
  • 4 Tbsp brown sugar
  • 4 Tbsp butter (slightly softened)

Instructions

  • Preheat oven to 375 degrees F (190 C).
  • Cream sugars and butter with mixer; add egg and beat until combined.
  • Add dry ingredients to a sifter. Alternate adding milk and dry ingredients to the butter mixture while mixing. Then add vanilla and stir.
  • Chill for 30 minutes before rolling out. Roll out into a rectangle on floured surface, spread with butter, pumpkin butter and top with brown sugar, cinnamon and pumpkin pie spice.
  • Carefully and tightly roll into a log, then use floss or a serrated knife to cut into equally thin slices.
  • Transfer to a baking sheet (they won't spread much) and bake for 14-15 minutes, being careful not to over-bake. They will be a little tender looking, but take them out, let them rest for 3-4 minutes on the baking sheet, and then transfer them to a cooling rack.

Notes

*Nutrition information is a rough estimate.

Nutrition (1 of 24 servings)

Serving: 1 cookies Calories: 145 Carbohydrates: 20 g Protein: 2 g Fat: 6 g Saturated Fat: 3 g Sodium: 71 mg Fiber: 1 g Sugar: 8.5 g

Pumpkin Cinnamon Roll Cookie Glaze

A rich 4-ingredient "caramel" glaze that comes together in minutes and tops these cookies (or actual cinnamon rolls) perfectly.
Author Minimalist Baker
Print
Stirring a pot of Caramel Cinnamon Roll Glaze
4.86 from 14 votes
Cook Time 5 minutes
Total Time 5 minutes
Servings 24 (cookies)
Course Dessert
Cuisine Gluten-Free, Vegetarian
Freezer Friendly No
Does it keep? 3 Days

Ingredients

  • 4 Tbsp butter
  • 1/2 cup brown sugar
  • 2 cups powdered sugar
  • 1 splash milk

Instructions

  • Melt butter in a saucepan over medium-low heat.
  • Add brown sugar and stir. Simmer the mixture while stirring frequently for 2-3 minutes.
  • Remove from heat and add powdered sugar and milk and stir. If you desire a thicker or thinner frosting, compensate with more milk or powdered sugar.
  • Spread or pour the glaze over the cookies (I used a spoon), sprinkle with more cinnamon or pumpkin pie spice (optional) and enjoy!
  • Store in an air-tight container at room temperature to keep fresh for at least 3 days.

Notes

*Nutrition information is a rough estimate.

Nutrition (1 of 24 servings)

Serving: 1 cookies Calories: 67 Carbohydrates: 0 g Protein: 0 g Fat: 1.9 g Saturated Fat: 0 g Polyunsaturated Fat: 0 g Monounsaturated Fat: 0 g Trans Fat: 0 g Cholesterol: 0 mg Sodium: 0 mg Potassium: 0 mg Fiber: 0 g Sugar: 12 g Vitamin A: 0 IU Vitamin C: 0 mg Calcium: 0 mg Iron: 0 mg

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  1. Hannah says

    These were so good! Definitely make the glaze as they are dry on their own but I gave them to people who normally dislike pumpkin and even they liked these! Definitely worth making!

  2. Ana Houghton says

    this recipe didn’t work for me – can you be more explicit with the steps – I feel like it would be tasty but … my first attempt was a catastrophy

    • Avatar for Dana @ Minimalist BakerDana @ Minimalist Baker says

      Hi Ana! Sorry you had trouble. I haven’t made this recipe in such a long time, but will review the steps to see if I can make it more clear!

  3. Nosizwe says

    They are absolutely deiicious! Confession: I know why the dough is extra soft – my half cup measure wasn’t. It was a third cup measure – hahaha! That’s what comes of rushing! I used baked mashed pumpkin and preserved ginger with lots of cinammon and mixed spice. SOOOOO good! Thank you.

  4. Nosizwe says

    Just made these coz they look yum. Substituted various things as can’t get pumpkin pie spice or pumpkin butter – not serious as I’ve made cinammon rolls before. Thought this would be an easier dough to work with. However, that’s not the case – the individual rolls have melded into one in the oven – the dough was too soft to start with I think. I’m sure they’ll taste good though.

    • Avatar for Dana @ Minimalist BakerDana @ Minimalist Baker says

      Yes, the dough is soft but if you just throw it in the fridge for a few minutes before cutting them into individual cookies they should be fine. Hope they still turned out OK!

  5. Iris says

    I just made these and they taste AMAZING! The caramel icing really adds a whole new element (because duh, I tried a cookie straight out of the oven AND one with icing for a taste test). My only question is: how did you get yours shaped so well? For some reason I found my dough melted quickly enough so that despite a super floured surface it still stuck to my board and was really difficult to roll? Any suggestions?

  6. Kathleen @ KatsHealthCorner says

    You are an absolute GENIUS, Dana!!! :D Those are so cute — what a great treat for the holidays (or any other time of year period!)! :D

  7. Lauren says

    these look GREAT! I’ve been looking for a yummy fall cookie to make. Just wondering, how did the texture turn out on these? are they crunchy? Chewy? Thanks!

    • Avatar for Dana @ Minimalist BakerDana @ Minimalist Baker says

      Thanks Lauren! The texture was still soft, not really crunchy or chewy. More like a traditional soft sugar cookie with a gooey center and decadent glaze!

  8. lw says

    I have the same thing for cinnamon rolls too, actually anything with cinnamon just feels so comforting somehow, especially in a chilly weather. its nearly getting warmer here where I live, but I’ll definitely give this recipe a go sometime. It just looks amazing!

  9. Veronica says

    I love this! I’ve made plain ones (cinnamon roll sugar cookies) but I love your healthier pumpkin take here…and the caramel icing is just the icing on the … cookie. :)

  10. Averie @ Averie Cooks says

    you are quite the pumpkin-recipe making machine :)

    love the roll-up nature of these cookies and that they’re cinn rolls!! and the icing – everything about it is just awesome!