I’ve been obsessed with classic cocktails lately, and there’s one quietly charming drink I can’t stop coming back to: the Up to Date. It’s that sweet spot between the laid-back Old Fashioned and the brooding Manhattan – complex, but not intimidating.
I still remember my first Up to Date. It was a blustery night in Chicago at one of those half-hidden speakeasy spots. The bartender, all suspenders and wry smiles, described it as “whiskey-forward, but with some real conversation going on underneath.” He couldn’t have put it better – every sip felt like unfolding a secret.
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This cocktail has some serious history, dating back to Prohibition-era bartenders who had to get creative with what they had on hand. Back then, calling something “Up to Date” wasn’t ironic – it was actually smack in the center of what was stylish and new. For years it faded into obscurity, but now, with the craft cocktail revival, it’s enjoying a well-deserved comeback. Honestly, after my first taste, I wondered how it ever slipped off the radar.
What keeps me coming back is the way spicy rye whiskey sets the scene – bold and a little peppery – then in comes the sherry, adding this delicate, nutty depth that you just won’t find in most whiskey drinks. Grand Marnier sneaks in a warm, citrusy sweetness, tying it all together without stealing the spotlight.
Here’s my go-to recipe:
- 1.5 ounces rye whiskey (Rittenhouse is my current favorite – big flavor, stands up to the other ingredients)
- 0.5 ounces Amontillado sherry (its subtle nuttiness is unbeatable)
- 0.5 ounces Grand Marnier
- 2 dashes Angostura bitters
- Lemon peel, for garnish
I always reach for a coupe glass for this one – the broad rim lets the aromas really open up, and let’s be honest, it just feels festive. But if I’m short on coupes, a trusty martini glass works just fine.
How I make it:
- Fill a mixing glass with big, cold ice cubes.
- Pour in the rye and sherry.
- Add Grand Marnier and the bitters.
- Stir for a good half-minute. You want it chilly, a little watered down, but not overdone.
- Strain into that pre-chilled coupe.
- Twist a strip of lemon peel over the drink to release the oils, run it around the rim, then drop it in.
A few times, I’ve mixed up a non-alcoholic version for friends – apple juice for whiskey, orange juice for Grand Marnier, and a couple dashes of non-alcoholic bitters. Admittedly, it’s its own thing, but weirdly, it still captures the essence – layers, aromas, a little mystery.
Food-wise, the Up to Date is a natural with a salty charcuterie board. Savory meats and cheeses love the cocktail’s spicy, sweet, and nutty notes. Sometimes I break out some dark chocolate alongside – those bitter, rich flavors work magic with the drink’s orange and sherry. When I’m feeling extra, I’ll grill a few veggies; their smokiness just sings with the cocktail.
Last weekend, just to shake things up, I swapped in bourbon for the rye. The result? Softer, smoother, a touch sweeter, which made my bourbon-loving friend grin ear to ear. One sunny afternoon, I topped an Up to Date with a splash of club soda – suddenly it was the perfect, bubbly patio sipper.
If you want to stretch your cocktail repertoire without wandering too far afield, the Up to Date is a no-brainer. It’s approachable but rewarding, and equally at home at a dinner party or sneaked into your own quiet evening routine.
One last tip: use a sherry you’d actually want to sip on its own, not the dusty bottle in the back of the pantry. And never skip chilling your glass – seriously, it’s a small detail that makes every sip brighter and better.
Give the Up to Date a try. With a little care and a couple of good ingredients, you’ll have a new favorite classic on your hands.
