This dessert honors America's oldest fruit tree, a pear tree brought from Europe around 1630 and planted in Massachusetts. Here, we poached Bosc pears in a Tennessee whiskey-spiked liquid perfumed with vanilla bean and orange zest.
Core pears from bottoms, using a small melon baller to scoop out seeds. Cut a round of parchment to the diameter of a pot just large enough to fit pears on their sides in a single layer.
Bring sugar and 4 cups water to a boil in pot, stirring until sugar is dissolved. Add 2 cups whiskey, vanilla bean and seeds, and orange zest. Nestle pears into liquid, laying them on their sides (if not fully submerged, add more water). Bring to a boil, then reduce heat to medium-low and place parchment round on top. Gently simmer until pears are just knife-tender, about 20 minutes.
Carefully transfer pears to a plate with a slotted spoon. Return poaching liquid to a boil and continue boiling until reduced to 4 cups, about 10 minutes. Strain liquid through a fine-mesh sieve into a large bowl. Stir in remaining 1/4 cup whiskey; let cool completely. Place pears in liquid. Cover and refrigerate until cold, at least 8 hours and up to 1 day. Halve pears lengthwise and serve chilled, with scoops of ice cream drizzled with molasses.