Prepare the fruit: Wash all the fruit thoroughly. Core and slice the apples and pear into thin wedges (leave the skin on for color and texture). Slice the orange into thin rounds, then halve those rounds.
Combine the base ingredients: In a large pitcher, pour in the red wine, bourbon, apple cider, and maple syrup. Stir gently with a wooden spoon until the maple syrup is fully incorporated.
Add the fruit and spices: Add the sliced apples, pear, orange, cinnamon sticks, and cloves to the pitcher. Gently press the fruit with your spoon to release some juice but be careful not to mash them.
Allow flavors to infuse: Cover the pitcher and refrigerate for at least 2 hours, but preferably overnight (up to 24 hours) to allow the flavors to fully meld together. The longer it sits, the more pronounced the flavors will become.
Serve with care: When ready to serve, give the sangria a gentle stir. Fill glasses halfway with ice if desired, then pour the sangria over, making sure to include some of the soaked fruit in each glass.
Add the finishing touch: Top each glass with a splash of club soda or ginger beer for a slight effervescence. Garnish with a fresh cinnamon stick and an apple slice.