
To rim the glasses, spread the crushed graham crackers onto a small plate. Pour a little maple syrup on a second plate. Gently run the edge of the rim around in the maple syrup, then in the crumbs so they adhere.
Fill a cocktail shaker with ice. Add the vodka, half-and-half, pumpkin, maple syrup, pumpkin pie spice, and vanilla. Shake for a solid 30 seconds to vigorously to combine and dilute (it's longer than you think!).
Strain into the glasses. Garnish with a cinnamon stick.