nb: for my sober folks, this is easily turned into a warming cider drink by halving the lemon juice and subbing in apple cider, orange pekoe tea (like Constant Comment), or a combination of the two for the whiskey. Serve iced or hot.
Oh, and none of the links are affiliate. I’m just sharing what I use because I like you.

It’s my favorite season! Though I am an unapologetic oenophile, it can’t always be French Riesling and Nebbiolo. Santé!
Ingredients:
Whiskey- I use Bulleit or Mine Hill (a local distillery) bourbon
Lemon juice, not from concentrate
Brown sugar simple syrup
Cherries: I like the freeze-dried tart ones from TJ’s or for a splurge, Amarena from Italy
Mulling spices, or at the very least, cinnamon
Method:
Make a spiced brown sugar simple syrup by dissolving equal parts dark brown sugar and water in a saucepan and add in spices to taste. I use this simple syrup in everything, from coffee to dessert to cocktails, so I make it in big batches: a few cups of water and a few cups of sugar and a few tablespoons of mulling spices. Sometimes I’ll throw in some star anise for fun. Don’t let the mixture boil; just dissolve it and stir until it’s clear, then store in the fridge. I use these bottles when I make a lot or these when I make less.
Add equal parts whiskey, lemon juice, and spiced brown sugar simple syrup to whatever vessel you’ve got going. Pour it over a bunch of ice, or one giant ice cube or sphere. When I entertain I use these or these. Smash a couple of freeze dried cherries and throw the dust on top. Garnish with more cherries. I am a libertine, so I add too many (probably). By the end of the drink, they’re nearly rehydrated like plump, sweet-tangy bombs.