The classic Rob Roy (sweet vermouth, scotch, a dash of bitters and a maraschino cherry) is pretty delicious on its own. The sweetness of the vermouth cuts smoky intensity of neat scotch. But for holiday's sake, a twist: replace the maraschino cherry with tart cranberries and add simple syrup flavored with cranberries, orange, vanilla and brown sugar. —Freckle & Fair
Boil ingredients for simple syrup on low heat until cranberries burst and cook down. Be patient — this process might take a while! If you cook the cranberries on too high of heat, the might explode a bit wildly and spray you.
Once the cranberries have cooked down into a smooth, sauce-like consistency (yes! this process is not unlike making cranberry sauce) remove from heat and strain remaining fruit pieces out using a mesh strainer.
Cool simple syrup to room temperature until you're ready to use it. I always speed this process up with the freezer because I'm impatient for cocktail time.
Add ice to a cocktail shaker with 1 ounce simple syrup, 1 ounce sweet vermouth and 2 ounces scotch. Garnish with a few fresh cranberries for extra tartness and color, and add a dash of bitters.