Pumpkin pie is central to my Thanksgiving celebration, and it's the one thing that I tend to sneak downstairs late at night to snack on before anyone else gets the chance. Recipes certainly vary, but pumpkin pie leans towards the savory side of desserts, which is the trick in terms of wine pairing. A medium-sweet wine with herbal or nutty flavors plays especially well with the nutmeg and ginger in a classic pie.
Dessert wines that have been exposed to oxygen have a more caramelized and savory flavor that marries well with pumpkin. Those from Rivesaltes, a region in the Roussillon in southern France, are made by stopping fermentation midway with the addition of a spirit, resulting in residual sugar and higher alcohol levels. There are many styles, but those labeled "Ambré" are made from white grapes like Macabeu and Grenache Blanc, and are exposed to oxidation as they age. For pumpkin pie, 2003 Domaine Singla Rivesaltes Ambré 'Héritage du Temps' is an ideal companion, and has plenty of acid and minerality to temper the sugar.
Sherry from Spain is another great option to complement the earthiness of pumpkin pie. The Amontillado style of sherry starts its life under flor, the local yeasts that grow on top of the wine and protect it from oxygen, resulting in complex and salty flavors. In Amontillados the flor dies, and the wine is subsequently exposed to oxygen, adding that nutty quality that pumpkin pie loves. Most are dry, but some have a small amount of Pedro Ximénez (a sweeter style of Sherry) blended in, resulting in a particularly dessert-friendly Amontillado. We love the easy-to-drink Valdespino 'Contrabandista'—each sip is all sugared hazelnuts and salted raisins.