Maple Frostbite

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1. 1
   Blend ½ cup granulated sugar, 1 oz. amontillado sherry or ½ tsp. vanilla extract (if using), and ½ cup water in a blender on medium speed until sugar is dissolved, 30 seconds–1 minute; there should be no grit left. Pour into a resealable container and add ½ vanilla bean, split lengthwise. Let sit at room temperature at least 4 hours or up to overnight.
2. 2
   Strain sugar mixture through a fine-mesh sieve into another airtight container (you should have about 1¾ cups). Cover and chill until ready to use. Do ahead: Vanilla syrup can be made 1 month ahead. Keep chilled.
3. 3
   Run 1 orange slice around half of the rim of a frappe glass. Lightly dip rim into powdered sugar to create a frosted appearance.
4. 4
   Combine 1 oz. fresh lemon juice, 1 oz. maple syrup, and ½ oz. vanilla syrup (or ½ oz. simple syrup plus ¼ tsp. vanilla extract) in a cocktail shaker. Fill shaker with ice, cover, and shake about 10 seconds, until just chilled.
5. 5
   Pour into prepared glass. Add 1 scoop (about ¾ cup) crushed ice. Fill glass to the top with chilled soda water (about 4 oz.), gently stir to combine, and garnish with orange half-moon (if using).