Begin by preparing your martini glass. Rim the edge with maple syrup and then dip it into graham cracker crumbs until well-coated. I've found that chilling the glass in the freezer beforehand helps the crumbs adhere better and gives an extra crispness to the drinking experience.
In a cocktail shaker, combine the vodka, pumpkin puree, heavy cream, pumpkin pie spice, maple syrup, and vanilla extract. The key here is to use pure pumpkin puree for its concentrated flavor, the pie filling varieties often come with added sugars and spices that can throw off the delicate balance of the drink.
Add a generous amount of ice to the shaker. The ice does more than just chill the drink; it dilutes the cocktail ever so slightly as it shakes, which is essential for softening the edges of the vodka and melding the flavors seamlessly.
Shake vigorously for about 30 seconds. You're looking for the shaker to become frosty on the outside, which is a telltale sign that the martini is well-chilled and properly aerated. The first time I made this, I under-shook, and the flavors hadn't fully married, the difference a good shake makes is remarkable.
Strain the mixture into the prepared martini glass. The straining is crucial as it leaves behind any unincorporated bits of pumpkin or spice, ensuring a smooth drinking experience.
If desired, top the martini with a dollop of whipped cream. This optional step adds a touch of decadence and visually mimics the classic pumpkin pie. I've always been apprehensive about garnishes, but in this case, it truly completes the cocktail.
Garnish with a cinnamon stick. Not only does it look elegant, but it also imparts a subtle aroma that enhances the pumpkin pie illusion. A dear friend, who's a mixologist, once suggested this garnish, and it's been a staple ever since.