Chocolate and Cinnamon? Absolutely! The combination of chocolate and warm autumn spices make an irresistible bite...and a surprising sandwich cookie. When I gave a plate of these Chocolate-Filled Pumpkin Cookies to a friend, she expected my tried-and-true vanilla bean cookie filled with dark chocolate ganache. She was pleasantly surprised by the cinnamon-sugar coating and the pumpkin spices in the cookie itself and how well these flavors complemented the chocolate. In between bites, she mused on whether she would share a few with her family or keep them all for herself. I’ll never tell!
“With no little kids to entertain for this holiday, I’ve left our pumpkins intact and decided to make edible Jack-o’-lanterns instead. Good choice!” Kasha
These chocolate-filled cookies are a great kick-off to the holiday season. The combination of cinnamon, ginger and nutmeg give them a cozy flavor and using brown sugar instead of granulated sugar makes them soft and chewy. I made several batches of these pumpkins and then decided to make another few dozen in the shape of leaves. No matter what shape they are, they’re really yummy and the perfect autumn treat.
Cookie specifics
Chocolate-Filled Pumpkin Cookies. These cookies were inspired by Half Baked Harvest’s recipe for “Milk Chocolate Stuffed Jack-O’-Lantern Cookies.” Tieghan recommended milk chocolate for the filling. When I’m making someone else’s recipes I always following their instructions the first time around.
I’m not a fan of milk chocolate, though, so after making the first batch as written, I made subsequent batches using semisweet chocolate and also a batch using white chocolate ganache for the filling because my sister is allergic to chocolate, but is able to tolerate white chocolate.
If you want to try this recipe for yourself, I recommend that you use the kind of chocolate you like to eat: milk, semisweet, dark, or white. Can’t go wrong with that approach! P.S. I really liked Tieghan’s method for the cinnamon-sugar coating. She brushes the cookie top with brown butter before sprinkling on the cinnamon-sugar, which adds a lovely caramel-y flavor to the cookie ... brilliant.
Shapes
pumpkin cutter, tiny triangle, tiny bat
Sizes
2½-inch pumpkin cutter, with a tiny ½-inch triangle cutter for the eyes and a tiny ⅞-inch-wide bat-shaped cutter for the mouth. See the slideshow above.
Dough Thickness
Since these are sandwich cookies, I rolled the bottom cookie ⅜ inch and the top cookie ⅛ inch. I think this gives the perfect ratio of cookie to filling in sandwich cookies.
Cookie Recipe from This Talented Cookie Artist
Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Original recipe from Halfbaked Harvest.
My tweaks: In the dough, I used European butter, added ¼ cup (38 grams) more all-purpose flour, omitted the baking soda so the cookies wouldn’t spread, and doubled the spices. In the cinnamon-sugar coating, I trippled the amount of cinnamon. In the filling, I replaced milk chocolate with semisweet chocolate. I also rolled the dough thinner: ⅜ inch for the bottom cookie and ⅛ inch for the top cookie. The dough is quite soft, so I cut out the shapes but before I moved them to the baking sheets, I popped the rolled-out dough in the freezer for 15 minutes. It makes it much easier to remove the cutout cookies from the dough.
To make it easier to remove the cutout pumpkins from the soft dough, place the rolled-out dough (with cutouts still in place) in the freezer for 15 minutes.
My Family Recipes
Semisweet Chocolate Ganache for Filling is a recipe I’ve developed over the years to make a ganache that is easy to spread and pipe onto cookies, and that will set up hard enough to stay in place, but not as dry as straight chocolate. It’s all about proportions! I use a 2:1 ratio of chocolate to cream (or water...yes, water!). Use a good quality baking chocolate that you like to eat out-of-hand. Make ganache filling a few hours before you’ll need it because it takes that long to set up and thicken.
White Chocolate Ganache for Filling. Because white chocolate isn’t really chocolate, making a ganache that is spreadable is a little bit tricker. Most of the time, I use a 3:1 ratio of white chocolate to cream (or water). But the weather makes a huge difference with white chocolate, so it has to be tweaked depending on whether my kitchen is cold or hot and whether the day is humid or dry. As with semisweet or dark chocolate ganache, use a quality baking chocolate. White chocolate ganache also takes longer to set up, so I usually make it the day ahead and let it sit covered, at room temperature until I use it.
Cookies
Chocolate-Filled Jack-O’-Lantern Sandwich Cookies: butter, light brown sugar, vanilla extract, egg, flour, cinnamon, ginger, nutmeg, salt
Fillings
Semisweet Chocolate Ganache Filling: semisweet chocolate, cream or water
White Chocolate Ganache Filling: white chocolate, cream or water
Coating
Cinnamon-sugar coathing: brown butter, cinnamon, sugar
Plate, Box or Bag?
Paper Plate. I made several dozens of these chocolate-filled sandwich cookies and man of them were delivered on a sturdy Chinet paper plate, wrapped in clear plastic wrap. This is a safe way to get them from my house to my neighbor’s house!
Box. My favorite way to transport my cookies is to package them in a cardboard bakery box with a clear window on top that makes the contents visible to anyone who wants to peek. These cookies were very cute smiling up through the window of the box!
Bags. I usually wrap most of the cookies individually in clear, food-safe bags, secured with a twist tie. This also makes the cookies stackable without causing damage to the decorations. And it protects them from germs when they're handed out to guests at an event. I”m always surprized at how many people take my cookies home to share with family and friends.
Mailing. For Halloween, packaged the cookies that I intended to mail to my family and friends throughout the U.S. in sturdy cardboard boxes. I always send them Priority Mail through the U.S. Post Office and frequently use the boxes provided by the Post Office... and lots of bubble wrap. In almost all cases, the cookies arrive undamaged. I know the packages are appreciated when they arrive because of the texts I get with all those smiling emojis.
What I’ve learned...
These cookies were made with the best ingredients I could find and baked in a small batch of two dozen. I’ve experimented with less expensive ingredients, but have come to the conclusion that flavor is best when I use the best. Why spend all this time baking and decorating if taste and texture are just so-so? Decorating the cookies takes time, but it’s an enjoyable process for me and I know that those who receive them appreciate that. Life is just better when you can share something you love with someone you love. Don’t you agree?
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