Cheese with Rum
Rum--it's not just for sloshing into Coke.
Good rum can be aged for 10+ years and is smooth and complex enough for savoring straight. While the diversity of flavors is huge, I expect warm spice (clove, allspice, cinnamon, licorice) and roasted or toasted undertones (tobacco, roasted chestnuts, butterscotch, brown butter).
I love the irony of the best rums hailing from the Caribbean while drinking them makes me think of mulled cider during New England fall.
On an accordingly gingerbread-y tip, try pairing with fat, whippy bloomy rinded cheeses: triple cremes like St. Nuage (exclusive to Whole Foods and aged by French affineur Herve Mons), Brillat Savarin or Cowgirl Creamery Mt. Tam all fill the "icing" slot.
For an entirely different approach, Alpine cheeses that are themselves heavy on roasty, toasty nuttiness amplify those qualities in your swallow of rum. Avoid mountain cheeses that are super washed as their caramel onion flavors can distract and compete. The classic go-to would be an aged Gruyere, but seek out the more exotic Bavarian Adelegger, Wisconsin's Pleasant Ridge Reserve or a really fine, 2 year aged summer-made Comte.