Place sugar in heavy 12-inch skillet and set over medium heat. Cook, without stirring, until sugar begins to melt; then stir until sugar is completely melted. Add pears (caramel will harden). Allow mixture to cook without stirring for 5 minutes. Cook until pears are crisp-tender, stirring occasionally, about 3 minutes longer.
Using slotted spoon, transfer pears to medium bowl. Add apple cider, dried cherries, lemon juice and cinnamon stick to caramel mixture in skillet. Simmer until any hardened caramel has melted, about 15 minutes. Remove from heat, discard cinnamon stick. Stir in brandy.
Preheat oven to 350ºF.
Lightly butter 13 x 10 x 2-inch baking dish. Spoon 3 tablespoons filling onto center of spotted side of 1 crepe. Spread filling to within 1 inch of edge of crepe. Roll crepe up from bottom. Place filled crepe, seam side down, in prepared dish. Repeat with remaining crepes and filling. Brush crepes lightly with melted butter. Cover dish with foil.
DO-AHEAD TIP: Crepes can be prepared 1 day ahead. Cover crepes and remaining sauce separately and chill.
Bake crepes, covered, until heated through, about 25 minutes. Rewarm sauce in heavy small saucepan over medium heat. Place 2 crepes on each of 8 dessert plates. Pour warm sauce over crepes. Serve with vanilla ice cream.
TENDER DESSERT CREPES: Whisk flour, sugar and salt in large bowl to blend. Whisk eggs, milk, water and 6 tablespoons melted butter in medium bowl. Pour egg mixture into flour in slow stream, whisking to remove any lumps. Strain batter into 4-cup glass measuring cup. Cover and refrigerate batter at least 1 hour.
For crepes, have following items by stove-top: crepe batter, melted butter, pastry brush, cake rack, 7- to 8-inch-diameter crepe pan, and 1/3-cup measuring cup.
Heat crepe pan over medium-high heat until very hot. Brush with some of remaining melted butter. Whisk batter, then pour 1/3 cup batter into pan, swirling batter around by tilting pan to fully coat bottom. Cook until golden brown on bottom, about 1 minute. Flip crepe over with large flat spatula and cook second until browned in spots, about 40 seconds. Transfer crepe to rack to cool. Brush skillet with butter (each time) and repeat process with remaining batter. (Make sure to whisk batter every few crepes.)
Once crepe has cooled, place it on sheet of wax paper. Pile crepes on top of each other with wax paper between each. Place stack of crepes in plastic bag and refrigerate or freeze until ready to use. (If frozen, thaw in refrigerator before filling.)