This cocktail recipe calls for cinnamon simple syrup (recipe below), but if you don't have time to make a simple syrup, there are other options.
If you choose to forego the simple syrup, you can simply break up cinnamon sticks in a shaker glass and muddle them with regular simple syrup and fresh orange juice. However, if you choose to prepare your Whiskey Smash this way, you will need to double strain your cocktail into your glass to avoid small bits of cinnamon getting into your drink. If you look at the photo above, that's what happened. However, when we used the cinnamon simple syrup instead (not pictured), this cocktail seemed to be more balanced with better cinnamon flavor.
So how do you make a cinnamon simple syrup?
It's actually quite easy. Combine equal parts water and sugar in a medium saucepan and heat until all of the sugar has been dissolved, stirring occasionally. Once the sugar has dissolved, add cinnamon sticks. Turn heat to low and allow the cinnamon sticks to soak in the simple syrup until your desired flavor is achieved.
We used 1/2 cup water, 1/2 cup sugar and 5 cinnamon sticks for about 10 minutes. If you prefer a little less cinnamon flavor, you can either reduce the number of cinnamon sticks or the time in which they soak.
Once you have achieved your desired flavor, allow the cinnamon simple syrup to cool and then strain it into a glass. This will keep in the fridge for about 14 days.
Combine all ingredients into a cocktail shaker. Add ice and shake vigorously. Strain into rocks glass over fresh ice. Garnish with a cinnamon stick and orange twists or orange slices.