Orange Butter Cookies with Chocolate Ganache

These simple orange butter cookies are flecked with orange zest, filled with smooth chocolate ganache, and taste identical to Pepperidge Farm Milano cookies. We absolutely devoured these buttery cookies and I know you’ll love the flavors!

orange butter cookies with chocolate ganache filling

Let’s Make Orange Butter Cookies!

Earlier this week I baked a batch of orange scented butter cookies and stuffed them with smooth chocolate ganache. This cookie recipe is straight from my dear friend Rebecca Firth’s new cookbook, The Cookie Book. Rebecca runs the blog Displaced Housewife. Her stunning photography and food styling is GOALS; I’m inspired every time I click over. Her new cookie cookbook, packed with 75 decadent and unique cookie recipes, is equally awesome. This fully photographed cookbook is made for all of us: cookie lovers and beautiful food enthusiasts!

Rebecca is gracious enough to let me share a cookie recipe with you and when deciding which recipe to publish, I found myself in a delicious dilemma. My eyes (and stomach) were immediately drawn to the Old Fashioned Iced Oatmeal Cookies. Then the Carrot Cake Bars and Red Velvet Madeleines and Pecan Brittle Bark Cookies and oh yeah, the Cold Brew Cookies. I finally decided on a shortbread-style cookie flecked with orange zest and filled with chocolate ganache. They’re sophisticated, simple, soft, and buttery and… best of all… they taste EXACTLY like Pepperidge Farm Milano cookies.

These orange butter cookies were supposed to be for the weekend but they never made it past Wednesday night. I know you’ll love them too!

the cookie book cookbook by Rebecca Firth

orange butter cookies with chocolate ganache filling

What Do They Taste Like?

Pepperidge Farm Milano cookies!

This cookie recipe begins a very familiar way: buttery cookie dough. You need butter, confectioners’ sugar, egg, an additional egg yolk for flavor, orange zest, vanilla extract, salt, and flour. If cut thick enough, these cookies are incredibly soft. Unlike sugar cookies which are typically crisp on the edges, these orange butter cookies are crumbly on the edges– very similar to shortbread. The orange gives the cookies a fresh flavor twist and is the perfect pair for that dark decadent chocolate ganache. Confectioners’ sugar, as opposed to granulated sugar, keeps the cookie thick and smooth. It also takes the place of some of the flour in the recipe, so these aren’t particularly dry like most butter cookies you’re used to. Rebecca, you’ve truly worked your magic.


Roll Out the Cookie Dough

After you prepare the dough, roll it out as if you were making my sugar cookies. This is a unique method that promises success, so follow the recipe closely.

  1. Divide dough in two pieces
  2. Roll out cookie dough on silicone baking mats or parchment paper
  3. Chill rolled out cookie dough for 1 hour
  4. Cut into shapes before baking

Notice that you roll out the dough BEFORE chilling it in the refrigerator.

  • Why before? The dough is so much easier to roll out before it’s chilled.
  • Why are we chilling it? So the cookies keep their shape when baked.
  • Why divide in 2? Because it’s difficult to roll out a huge mass of dough. Dividing into smaller sections makes rolling out more manageable.
  • Why on a silicone baking mat? Because you have to chill the rolled out dough in the refrigerator and you can’t really pick up a mass of dough you rolled out on the counter. Nor can you cut into shapes when the dough is this warm. So, roll the dough out on a nonstick surface that you can literally pick up, put on a baking sheet, and place in the fridge.

KitchenAid Misty Blue Stand Mixer

orange butter cookie dough rolled out before shaping

orange butter cookies cookie cutters

butter cookies on baking sheet

How to Shape Orange Butter Cookies

The only way to guarantee soft and thick orange butter cookies is to roll out the cookie dough to about 1/4-inch thickness. Rebecca uses an adorable fluted edge square cookie cutter in her cookbook, but I reached for my fluted edge circle cookie cutter. You can use any shape cookie cutter you’d like. Since you’re eating two cookies at a time sandwich-style, I suggest using a small cookie cutter to make petite sandwiches.

I used the 1.5 inch size from this cookie cutter set.

Cut the cookie dough after it’s chilled. I pressed some coarse sugar into the tops of each orange scented cookie before baking. This is optional, but adds a little crunch and sparkle.

Since we chilled the cookie dough, the cookies will hold their beautiful shape as they bake. Bake until very lightly browned on the edges. So delightful even without the chocolate ganache! I literally want to throw a tea party just to serve these orange butter cookies.

orange butter cookies

assembling orange butter cookies with chocolate ganache filling

Chocolate Ganache

Let’s sandwich them! Did you know you only need 2 ingredients for chocolate ganache? Chocolate ganache is made from warm cream and chopped chocolate. Make sure you let it cool and thicken before sandwiching in the cookies. Time saving tip: prepare the ganache as the cookies bake so it can cool down as the cookies cool.

After a couple hours, the ganache will set so you can stack and store the cookies. By day 2, the ganache will have softened the two cookies surrounding it AND that delicious orange flavor will be stronger. Each bite tastes like those orange flavored chocolate Milano cookies we all know and love!

orange butter cookies with chocolate ganache filling

Let’s give Rebecca a huge THANK YOU for these incredible cookies!

Print
butter cookie sandwiches with chocolate ganache filling

Butter Cookies with Orange & Chocolate Ganache

  • Author: Sally
  • Prep Time: 1 hour, 30 minutes
  • Cook Time: 10 minutes
  • Total Time: 2 hours
  • Yield: 20-24 sandwiches
  • Category: Cookies
  • Method: Baking
  • Cuisine: American

Description

Shortbread-style cookies flecked with orange zest and filled with thickened ganache. They’re sophisticated, simple, soft, and buttery!


Ingredients

  • 1 cup (2 sticks; 230g) unsalted butter, softened to room temperature
  • 3/4 cup (90g) confectioners’ sugar
  • 1 and 1/2 Tablespoons orange zest (about 1 orange)
  • 1 large egg, at room temperature
  • 1 large egg yolk, at room temperature
  • 1 and 1/2 teaspoons pure vanilla extract
  • 1/4 teaspoon salt
  • 2 cups (250g) all-purpose flour, plus more as needed for rolling
  • optional: coarse sugar for topping

Chocolate Ganache

  • 1/2 cup (120ml) heavy cream
  • 4-ounce semi-sweet chocolate bar (113g), finely chopped

Instructions

  1. Preliminary note: The chocolate ganache requires at least 30 minutes to thicken before it can be used in the cookie sandwiches. I recommend starting the ganache as the cookies bake!
  2. In a large bowl using a hand-held or stand mixer fitted with a paddle attachment, beat the butter on medium high speed until completely smooth and creamy, about 2 minutes. Add the confectioners’ sugar and orange zest, then beat until combined, about 1 minute. Next, add the egg, egg yolk, vanilla extract, and salt. Beat on high speed until combined, scraping down the sides and up the bottom of the bowl as needed. Finally, beat in the flour on low speed until combined. The cookie dough will be soft.
  3. Lightly flour your hands, work surface, and rolling pin. Divide the dough into 2 equal parts. Roll each portion out onto a piece of parchment paper or a lightly floured silicone baking mat (I prefer the nonstick silicone mat) to about 1/4-inch thickness. The rolled-out dough can be any shape, as long as it is evenly 1/4-inch thick.
  4. Stack the pieces, with parchment paper between the two, onto a baking sheet and refrigerate for at least 1 hour and up to 2 days. If chilling for more than a couple hours, cover the top dough piece with a single piece of parchment paper.
  5. Once chilled, preheat oven to 350°F (177°C). Line 2 large baking sheets with parchment paper or silicone baking mats. Remove one of the dough pieces from the refrigerator and, using a 1.5-inch cookie cutter, cut into shapes. I used the 1.5 inch fluted round cookie cutter from this adorable set. Re-roll the remaining dough and continue cutting until all is used. Repeat with 2nd dough piece. Arrange cookies on baking sheets 2 inches apart. If desired, sprinkle + press some coarse sugar into the tops.
  6. Bake cookies for 9-10 minutes until very lightly browned around the edges. Make sure you rotate the baking sheet halfway through bake time. Allow cookies to cool on the baking sheet for 5 minutes then transfer to a wire rack to cool completely before decorating.
  7. Make the ganache: Place chopped chocolate in a bowl. Heat the cream in a small saucepan until it begins to gently simmer. (Do not let it come to a rapid boil– that’s too hot!) Pour over chocolate and let it sit for 2-3 minutes to gently soften the chocolate. Slowly stir until completely combined and chocolate has melted. Allow to cool and thicken for at least 30 minutes or until spreadable consistency.
  8. Spread the ganache onto the flat side of one cookie and sandwich with the other. Repeat with remaining.
  9. Cookies will stay fresh covered at room temperature for 3 days or in the refrigerator for 1 week.

Notes

  1. Make Ahead Instructions: Chocolate ganache can be prepared, covered, and refrigerated for up to 3 days before using. Let it sit at room temperature to soften or microwave for 5-10 seconds before using. Plain (un-sandwiched) cookies freeze well up to 3 months. Thaw overnight in the refrigerator. You can chill the rolled-out cookie dough in the refrigerator for up to 2 days (step 4). You can also freeze the cookie dough, before rolling out in step 3, for up to 3 months. Then allow to thaw overnight in the refrigerator and bring to room temperature before rolling out. Chill for only 30 minutes in step 4 as opposed to 1 hour.
  2. Special Tools: KitchenAid Stand Mixer | Glass Mixing Bowls | Rolling Pin | Fluted Edge Round Cookie Cutters | Silpat Baking Mat | Baking Sheet | Cooling Rack | The Cookie Book
  3. Be sure to check out my top 5 cookie baking tips AND these are my 10 must-have cookie baking tools.

Oh and instead of chocolate ganache, try filling with salted caramel. Let the caramel cool for 15 minutes before sandwiching!

Flecked with orange zest and filled with caramel, these shortbread cookie sandwiches are simple and sophisticated all in one! Recipe on sallysbakingaddiction.com

95 Comments

  1. These look so good Sally!!! Orange is my favourite fruit and I LOVE it in cookies!! Could I make the ganache with sweeter chocolate instead?

  2. Yum! These look delightful! My stomach is growling already haha. But is it possible to remove the orange flavour completely? Not a fan of orange…

  3. Oh my gosh, my mother and I LOVE milano cookies… I think I just found my weekend baking goal!! Seneca Lake is wonderful, I hope you have a great trip! Living in northeast PA, I’ve been up there plenty of times. I recommend brunch at the Belhurst on Sunday (SO GOOD), and I do remember seeing plenty of little kids there when I went, so I’m sure it’d be fine with the babies! We also had lunch at The Weinery on the west side of the lake, and it was fantastic. I got chorizo sausage and peppers with some fancy additions. And also if the men of the group are looking for beer, the Climbing Bines Brewery was a fun change from all the delicious wine. That’s on the west side of Seneca too. Okay, I’ll stop now haha… have fun!

    1. I live in the area – you are in for a treat.
      FLX Table in Geneva was voted the best new restaurant in America by the USA Today a year or two ago. And I LOVE Kindred Fare in Geneva. So GOOD! There is an authentic German place in Canandaigua (Rheinblick) that’s a blast. Also in Canandaigua is the NYS wine and culinary center. I hope you stop – it’s wonderful! The wineries are all fun and great – especially if you like Riesling. But I prefer Keuka to Seneca.
      Have a great trip! Upstate NY / finger lakes region is a jewel☺️

  4. YUM I love orange and chocolate together- and is it just me or are these not the PERFECT Halloween treat?? The slight orange color in the cookie from the zest + Dark chocolate ganache- I think these would be so cool on a Halloween dessert tray! Enjoy the weekend! I’ve never been up there but would love to go. Please do share with us any cool spots you find! 🙂

    1. Hi Megan! Heavy cream is what will set up the ganache. You need all that fat + thickness. Full fat coconut milk works instead if you have that around!

  5. I’m looking for cookies for holiday gift plates. Can these sit out for several days safely? Are they sturdy enough to be stacked and nestled in among other types of cookies? Thank you – these look amazing!

    1. Yes and yes! I kept these out at room temperature for several days and they were still fantastic– even softer and more flavorful. They stack easily once that ganache is set.

      1. Reporting back 🙂 These butter cookies are incredible! I used ganache and they sure did taste like milano cookies. Thanks again, Sally!

  6. Wow! These are gorgeous! I didn’t know how much I needed these cookies! Thank you, Sally, for sharing another delicious recipe.

  7. LOVE the idea of orange and chocolate together! I haven’t made butter cookies in ages; can’t wait to make these!

  8. My suggestion for your trip… Dano’s Heuriger On Seneca for a lunch or brunch on the east side of Seneca Lake, about halfway down. Bring your Viennese appetite!

  9. Sally this is a gorgeous post!! Your photography is so beautiful and I love all of your Cookie detail!! I’ve always been such a fan of your work but I am just blown away by your kindness and support — you are truly a gem!!! So much love + gratitude to you!!!! xox

  10. And I forgot to add:
    Thank you so much for all your wonderful recipes! Your site is a refreshing change from so many of the other food and recipe sites. You are a gem!

  11. Milano cookies are my son’s favorite! I will for sure make these for him for his birthday next month. Trader Joe’s used to have a knock off Milano cookie that was better than the original, but I think Nabisco (or whoever makes Milanos) sued them. Then it took 2 years, they repackaged them, had them in stores about 2 weeks, and then poof– gone again!! So—now I will just have to make them myself! Thank you!

  12. AHHHHH!!! Sally, you must have been reading my mind!!! I am OBSESSED with the chocolate orange Milano cookies, but I can never find them any more in any local stores. You have answered my prayers!! Lol. Can’t wait to try this recipe!!

  13. We went to the Finger Lakes 21 years ago. So sorry, but I cannot remember any place to recommend. We mainly stayed in the house we were all renting and took turns cooking. We had 5 couples and 2 toddlers…and one of the ladies was newly pregnant with twins! Hope your time there is more relaxing. The cookies look super yummy and will be added to my cookie list!

  14. My current “must do’s” in the Finger Lakes:

    Ithaca Farmer’s Market
    Hazelnut Kitchen (restaurant in Trumansburg – totally amazing; local food)
    Moosewood Restaurant in Ithaca (the original!)
    Sapsucker Woods Sanctuary or Taughannock Falls State Park for some beautiful trails and scenery

  15. The restaurant at Glenora winery on Seneca lake is wonderful. Not sure if it will be warm enough, but their outside deck is beautiful too! http://www.glenora.com/Restaurant/Veraisons-Restaurant

    1. Thank you so much for the suggestion Jen! We didn’t get a chance to go there, but the weather was beautiful and we plan to visit again.

  16. Sally, I just have to tell you how much I enjoy your posts. I have been there as you’ve grown and today I can tell you that I consider ou the best all around blogger on baking. And all that with a one year old!
    Your instructions are clear, you tell why you go it, how you do it, remind us of tips you’ve given, and I have never had a bad recipe from you. You are so thorough and thoughtful. I never hesitate to print out and make your recipes for the first time to take somewhere and always get so many compliments. I commend you on your success and wish you even more. I know this must sound gushy but I am sincere about every word. Thank you!

  17. Sally,
    The cookies look great- but my hubbie and I have spent the last 8 labor day weekends in Seneca lake at a fabulous b&b in Geneva (named after a flower) and love our time there. I hope you are enjoying your time as well- and the Riesling!

  18. Hi, We make an annual Mid September trip to the Finger Lakes, re-visiting some
    Wineries & adding a couple new ones each year. Favorites are: on west side of Seneca Lake: Fulkerson Winery: very nice folks & we love a lot of their wines. Their delicious Brandywine apples may be available in tasting room/ gift shop near check out counter. They also have fresh grape juice available sometimes during harvest. On the east side of Seneca Lake our favorite is Wagner Winery. Again, great folks & we enjoy their wines. They also have a Brewery as well as a restaurant(that we’ve yet to try). Both of these wineries ship to us in Maine throughout the year. We like both of their wine clubs. Have a wonderful time exploring the beautiful Finger Lakes !

  19. Hi, again! Re: Seneca Lake: CHEESE !
    This September trip we discovered: Shtayburne Farm in Rock Stream NY. website: fingerlakesdairyfarm.com
    If u r familiar with Cheese Curds, theirs r exactly like those we lovein Canada: I’ve always called them “squeaky cheese” because the best types “squeak” when u eat them ( That’s me, I’m easily amused in life. ) We enjoyed a lot of their cheeses. Last year, our first-ever Seneca Lake cheese stop was Muranda Cheese Company in Waterloo, NY up near north end of lake. They have a variety of aged cheeses. If u like Blue cheese, I happen to love theirs! Their cheeses are in tightly sealed packages of varying weights & keep well.
    Friends, babies, wine, cheese in Autumn in the Finger Lakes: I’d say that’s spectacular! By the way,I love your site/blog. All the best for continued success,

    1. Appreciate all the cheese recs! We didn’t have the chance to stop at Muranda Cheese Company, but there’s always next time. And I LOVE blue cheese!

  20. I made them in a flower design, sooo cute! I posted on FB, I don’t do Instagram.
    However, I would like them to be sweeter. any suggestions?

    1. I bet they are so pretty! Did you post in my Facebook group? Sorry if I missed it, I was traveling this weekend. 🙂 Butter cookies aren’t very sweet, but you could try replacing some of the flour with confectioners’ sugar. I fear they will spread a bit more, but it’s worth a shot!

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