Slice your apple and lemon into thin wheels (about 1/8-inch thickness) and set them aside on a small plate. This prep work ensures your garnishes are ready when you need them and prevents a soggy presentation. While you're prepping, I like to use this time to select your glassware—a rocks glass works perfectly for this drink and can be chilled in the freezer while you work.
Pour the bourbon, apple cider, freshly squeezed lemon juice, and pure maple syrup into a cocktail shaker. Add a dash of freshly ground cinnamon and allspice, then finish with a dash of orange bitters. The spices and bitters distribute better when added to liquid, which ensures even flavor throughout your drink. Stir gently to combine the ingredients before shaking.
Fill your cocktail shaker with ice until about three-quarters full, then seal and shake vigorously for 10-15 seconds. You'll know it's ready when the outside of the shaker becomes frosty and cold to the touch. I always shake a bit longer with apple cider drinks because the natural sugars need extra time to chill properly and meld with the other flavors.
Fill your rocks glass generously with fresh ice cubes, then strain the shaken mixture from the cocktail shaker into the glass. The fresh ice in the glass (rather than using the shaking ice) prevents over-dilution as you continue to serve the drink. Aim for about 3-4 ounces of liquid in your glass.
Top the drink with club soda to taste—start with about 1-2 ounces and adjust based on how bubbly you like your drink, or use ginger ale if you prefer a spicier variation. Carefully arrange your prepared apple and lemon slices on the rim or float them in the glass for a beautiful presentation. Give the drink a gentle stir to incorporate the soda, and serve immediately.