Whiskey Sours are a serious tradition in my family. For as long as I can remember, my grandfather would make these classic drinks for every holiday or get together we’d have. I’m reasonably certain it was the first cocktail I ever tried, likely given to me when I hit an age where I felt too old for Shirley Temples (little did I know there is no such thing). The drink was handed to me full of bright red maraschino cherries and giant wedges of orange, and was quite likely heavily diluted. It was delicious and citrusy and sweet.
When my now-husband Sam came his first holiday with our family some years ago, he was introduced to this tradition. Always the solicitous host, my grandfather offered him wine or one of his famous Whiskey Sours. Sam accepted the mixed drink, and (while he didn’t drink much) he too was hooked. Nowadays, it’s one of the very few cocktails he’ll order on a regular basis.
We even served Whiskey Sours as our signature drink at our wedding a couple years ago. By sheer coincidence, it was a perfect fit for our 1930’s travel, jazz (and actually Indiana Jones) inspired wedding – but that’s a story for another day.
As time has passed, I’ve dutifully taken over my grandfather’s task of making large batches of Whiskey Sours for our family. A traditional Whiskey Sour is easy to make – simple syrup, lemon juice, Cointreau (or triple sec), and whiskey. My grandfather made them with these little packets of powdered mix – just add water and whiskey. As I try to err towards more homemade ingredients, I sought a homemade recipe that would still meet family approval.
Just multiplying a standard recipe can get pricey, so to make a large batch that is a little more drinkable and a little less expensive, I followed Martha Stewart’s example and made a punch-like version that includes orange juice. This satisfies the sugar fix the artificial packets can carry, and the lemon juice adds the tart. It’s rounded out with homemade simple syrup, orange liquor (I’m partial to Cointreau), and the whiskey.
Oh, and of course, you can’t forget some absolutely delicious maraschino cocktail cherries.
Due to the sheer amount I end up making (and the number of flavors), I usually use a bottle of “the cheap stuff” (as my grandfather always insists on) for the whiskey portion. Feel free to elevate yours with a better label if you feel so inclined. So far, I haven’t gotten any complaints regarding the switch to real simple syrup and fresh juices, though. The recipe has even earned my grandfather’s high seal of approval, which is notoriously rare in our family.
I fall back on this recipe for all sorts of casual events. I love bringing a pitcher to picnics and recently made it for our Super Bowl party last month. The Whiskey Sours come together quickly and are always a crowd-pleaser. The punch travels well if kept in a well-sealed container (just give it a quick stir or shake if the ingredients start to separate). Just make sure you load up the glasses with maraschino cherries and piles of oranges, and you’ll be on the track to being a surrogate member of the family!
Large Batch Whiskey Sours
Adapted from Martha Stewart
- 4 cups orange juice I use store-bought Tropicana, but I’m sure fresh squeezed would be delicious
- 1 cup lemon juice
- 1 cup Cointreau or other orange liquor
- 2 1/2 cups whiskey
- 1/2 cup simple syrup, plus more to taste
- Splash of cherry syrup or grenadine to each glass
- Maraschino cherries and orange slices, to garnish
Combine all ingredients through the simple syrup in a large pitcher. Stir to combine. Serve each individual cocktail over ice with a splash of cherry syrup or real grenadine. Garnish each glass with one cherry (or more, I won’t judge!) and an orange wedge.
I like adding the cherry syrup (or real grenadine) to each glass to taste, and the recipe reflects this. If you'd rather not add it individually, you can instead stir a half cup (8 tablespoons) of cherry syrup or real grenadine into the pitcher to make it easier!