Friday Happy Hour: Winter Cobbler

Last March, we first introduced the Cobbler: a concoction of booze, sugar, and lots and lots of fruit that was once one of the most popular drinks in America. Just because that was a century and a half ago doesn’t mean you shouldn’t try one today. And just because the Cobbler is traditionally one of the most perfect summer drinks doesn’t mean you can’t enjoy one in winter. You just need to balance some winter fruit with some heartier, winter appropriate spirits to produce a rich and tart but sweet Winter Cobbler. – Andrew



Illustration by Shauna Lynn for Oh So Beautiful Paper

The Winter Cobbler

2 oz Bourbon
1 oz Dry Sherry
2 oz Cooked Cranberries
1 oz Cranberry Simple Syrup
Orange and Lemon Slices

Combine a cup of cranberries and a cup of simple syrup (1:1 sugar melted in water) in a saucepan and gently simmer until the cranberries start to pop or burst apart. Strain out the cranberries and reserve the rest of the cranberry syrup.


Combine the Bourbon, Sherry, cooked cranberries, cranberry syrup, and a handful of orange and lemon slices in a cobbler shaker with lots of ice. Shake vigorously. Pour everything, fruit and ice and all, into a glass. Garnish, if you need one at all, with some fresh cranberries. Enjoy!



The Bourbon provides a solid base of oak and vanilla, while the Sherry adds just enough nutty richness. The cranberries and lemon introduce plenty of tartness, balanced by the sweetness of the Sherry, simple syrup, and orange slices. There’s a lot going on in this glass. Comparisons to traditional holiday cranberry sauce, with all that tart but sweet and citrusy fruit, are not entirely out of place – but this shouldn’t be a boozy cranberry sauce in a glass. The fruit and sugar should complement the spirits and wine, not overwhelm them.


I love this drink in part because it reveals the enormous potential of classic drinks like the Cobbler. Once you’ve understood the basics of a drink like this, a mess of fruit and liquor in a glass, you’re free to play around with combinations that can suit any season or mood. There’s a reason the Cobbler used to be enormously popular. I just don’t understand why it ever stopped.

Photo Credits: Nole Garey for Oh So Beautiful Paper

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