Thinly slice the pears and figs. Heat a large skillet over medium-high heat.
Melt the butter and maple syrup together in the skillet. Use 1 tablespoon of butter and 1 tablespoon of maple syrup per quesadilla.
Place one tortilla into the skillet. Evenly top with ¼ of the sliced pears, ¼ of the sliced figs, ½ cup grated Gruyere, ½ cup grated mozzarella, and ½ cup baby arugula. Sprinkle with freshly cracked black pepper. Cover with a second tortilla.
Cook until the bottom tortilla is crisped and golden, about 2 minutes. Using a spatula on the bottom and your hand on the top, carefully flip the quesadilla. Cook another 2 minutes until the cheese is melted and the tortilla is evenly crisped.
Repeat for the remaining quesadillas. Slice and serve with Spiced Cherry Preserves, for dipping.
Spiced Cherry Preserves
Pit and stem the cherries, if using fresh cherries.
Combine the cherries, honey, balsamic vinegar, kosher salt, allspice, and cloves in a saucepan. Place over medium heat.
Cook over medium heat, stirring often, until the cherries are soft and the sauce is reduced, about 20-25 minutes.
Allow the preserves to cool. Using an immersion blender, traditional blender, or food processor, blend until smooth.