I like to push the envelope a bit with my desserts. The classics are delicious, and it is important to have good recipes for all the basics, but sometimes it is fun to push the desserts a bit further. That is exactly what I did with these cookies. Dreidel sugar cookies would be a welcome addition at any Hanukkah gathering (or you could try making them with gingerbread instead) but when people see an iced sugar cookie it isn’t necessarily a conversation starter. These cookies, however, are sure to be the talk of the party. They combine the classic combination of dreidels and gelt in a fun package. On the surface they look like tall sugar cookies, but break them open and out fall a bunch of chocolate gelt.

The gelt-filled  cookies are inspired by these filled piñata cookies I saw a while back. Those cookies are shaped like piñatas and when you break them open candy falls out. They are unbelievably cute, but I had no need for piñata cookies so I made these gelt-filled dreidels using the same basic method. They are a bit of work to make, but I thought the end result was worth it.

For these cookies I decided to try a new sugar cookie recipe. I figured since I have recipes I like that use margarine and coconut oil I should try a shortening recipe to see how it came out. This recipe is from the uber talented Melissa at Lil Miss Cakes. She makes such beautiful decorated cookies (and even more impressive cakes) so I figured she probably knows a thing or two about sugar cookie dough, and she sure does. These cookies are not only delicious, the dough is truly a pleasure to work with. If your shortening isn’t too warm the dough doesn’t even need chilling before rolling it out and the cookies don’t spread much at all when they are baked.

I also really love that this recipe uses shortening. I have been using shortening more lately with great results. It’s kind of funny, when people hear shortening they immediately think “unhealthy” and that is no longer true necessarily true. I use Spectrum Organic Shortening which is completely non-hydrogenated and natural. As far as I know there are no parve, non-hydrogenated margarines that are unsalted. That means that unless the recipe you use them in has enough salt to compensate for the difference the end result comes out a bit too salty. Using shortening is a great alternative. One of the downsides of shortening is that it is not particularly flavorful, but this recipe compensates by adding orange juice which gives it a nice subtle flavor. I will definitely be making these again.

If you want to make the gelt-filled cookies gluten-free follow the same instructions for cutting and baking using this gluten-free recipe instead. The gluten-free cookies do spread a bit while baking so as soon as you remove them from the oven (while they are still hot) recut them using the same cookie cutter.