Pumpkin Milano Cookies

Pumpkin Milano Cookies

Let’s talk pumpkin and chocolate, shall we?

Honestly, until this year, I hadn’t ever tried anything pumpkin and chocolate. I really thought the combination sounded terrible. Well, if you’re like me and have yet to give into this delightful combination, you’re missing out. I finally gave in and tried it and let me tell you it’s amazing. Still not quite up there with peanut butter and chocolate, but hey, what else is? The answer is nothing.

So anyway, as usual, the other night I was lying in bed and recipe ideas were swimming through my brain. Then, the greatest idea bubbled to the surface: PUMPKIN MILANOS! Hello?! Why haven’t I thought of this before?? I immediately grabbed my iPhone, pulled up my Evernote app and added it to my recipe ideas. By the way, it drives my husband crazy that I constantly light up our room like the 4th of July in the middle of the night to note my recipe ideas.

Pumpkin Milano Cookies

The next morning I begrudgingly pulled Google up and typed in “pumpkin Milano cookies.” It never fails that whenever I think I’ve got the most original, out-of-this-world recipe idea, it already exists. Like my brilliant idea to make a wine cake? Yeah, been done a thousand times. Or the time I developed a “crepe casserole” in my mind? Turns out it’s called a crepe cake.

But this time was different. Nothing! Ah ha! I was so excited, you should have seen me. I had no idea how to create a Milano cookie from scratch though; I mean that sounds nearly impossible otherwise why would I spend $5.00 on a bag of 4 cookies from Pepperidge Farm? Well, as luck would have it there are a couple homemade Milano cookie recipes out there! I just had to figure out how to add the pumpkin and spices. Let me tell you, these cookies are sooo yummy. I dare you to make them and try to eat just one. Double dog dare you. I will say that the texture isn’t really like a Milano cookie. Unfortunately, they don’t have a crisp, airy texture. It’s more soft and chewy, but that’s okay. Try it for yourself!

Pumpkin Milano Cookies

Pumpkin Milano Cookies

Serves 14
Meal type Dessert
Pumpkin milano cookies with fall inspired spices


  • 1 1/4 cup flour
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter (room temperature)
  • 2/3 cups sugar
  • 1/2 cup pumpkin puree
  • 1 egg (room temperature)
  • 1/2 teaspoon vanilla extract
  • 1/2 teaspoon ground cinnamon
  • 1/2 teaspoon ground nutmeg
  • 4oz semisweet chocolate


1. In a bowl, whisk flour and salt together.
2. In a stand mixer, beat butter and sugar together until light and fluffy. Add pumpkin, egg, vanilla and spices and mix on high until combined. On low speed, add flour mixture and stir until just combined.
3. Transfer the dough to a pastry bag with a tip (I used Ateco 804) or use a Ziploc bag with the end cut off. Line a baking sheet with parchment paper or heavily grease a baking sheet. Pipe 3/4 x 2 inch cookies onto the baking sheet, about 1/2 an inch apart.
4. Chill in the refrigerator 20 minutes or until firm.
5. Preheat oven to 325 degrees. Bake cookies about 15-17 minutes or until the edges brown slightly. Transfer to wire rack and cool.
6. Melt chocolate in microwave, stirring every 30 seconds. Spread chocolate on one half of a cookie and sandwich the cookie halves together.
7. Put back into refrigerator and allow chocolate to set.


Adapted from Try It You Might Like It

Store in airtight container


  1. 1

    Milanos were my all time favorite as a kid! And I love pumpkin and chocolate together!! Yumm! You are a genius, and you should tell your husband to chill about the midnight fireworks. It’s totally worth it : )
    Lisa recently posted..It’s Friday! Cheers! {Virtual Ribbon Cutting}My Profile

  2. 2

    Purty pictures! impressed with your recipe. I haven’t tried pumpkin and chocolate yet together. Hmmmm.
    Shiloh Barkley recently posted..Apple Cider Muffin TopsMy Profile

  3. 3

    I LOVE milanos – and these looks amazing
    this year was the first time I combined the two as well
    it works:)
    Heather recently posted..Peanut Butter Cup no-bake Granola BarsMy Profile

  4. 4

    These are Great! Love them!
    Karyn – Pint Sized Baker recently posted..How to make Tie-Dyed Cake PopsMy Profile

  5. 5

    Gah! These look awesome! I loved Milanos when I was younger. Must try these soon…

  6. 6

    OMG YOU ARE BRILLIANT!!!!!!! These look amaaaaazing. I love milanos and I’ve been loving pumpkin and chocolate lately :) Also, I love thinking of something that no one else has ever done (or at least posted about!) Such a good feeling–congrats :) Pinning now and cannot WAIT to make them!
    Erika recently posted..Pancake Fridays: Whole Wheat Pear and Chocolate PancakesMy Profile

  7. 7

    These look and sound amazing! Thanks for sharing :)

  8. 8

    My boyfriend and you’re husband would have something to gripe about then because I always light up our bedroom like the fourth of july when a recipe idea hits me. These pumpkin milano cookies though are proof that the best recipe idea’s happen at 1 am. YUM!
    Nicole recently posted..Gingerbread Caramel CornMy Profile

  9. 9

    Don’t you love it when you come up with something original?! It seriously is one of the best feelings. Only food bloggers will understand, but I’m right there with you. And this is a brilliant idea! I’m a sucker for anything pumpkin, so these look delicious. Pretty presentation too-perfect for a Thanksgiving party or get-together. :)
    Elaine recently posted..S’mores TrufflesMy Profile

  10. 10

    I absolutely love milano cookies. Your pumpkin milano cookies with semi-sweet chocolate look so good!!
    petit4chocolatier recently posted..Wickedly Chocolate Devilish Food Cupcakes & Chocolate Butter-cream Frosting topped with a Wisp of Fluffiness, Crushed Pecans and Dark Chocolate Covered CherriesMy Profile


  1. [...] really something and the recipes will get your sweet tooth kicking. These recipes look extra good: Pumpkin Milano Cookies, Polka Dot Cheesecake Brownies, Chocolate Pound Cake Cookies, Reese’s Chocolate Shortbread [...]

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