The Dempsey cocktail is one of those timeless drinks that always feels a little special. Bright, fruity, and just the right amount of bold, it mixes classic ingredients with a touch of old-school charm. With gin, applejack, lemon juice, and grenadine, this cocktail strikes a balance between tart and sweet—perfect for warm evenings or whenever you’re in the mood for something a little fancy without the fuss.
Dempsey
This has been my go-to cocktail for summer nights on the porch, and after making it countless times, I’ve picked up a few tricks to get it just right.
What You’ll Need
Prep Time: 5 minutes
Servings: 1 cocktail
Glassware: Cocktail glass or martini glass
Ingredients
– 1 oz (30 ml) gin
– 1 oz (30 ml) applejack (or Calvados for a smoother apple flavor)
– 1 oz (30 ml) freshly squeezed lemon juice
– ½ oz (15 ml) grenadine (or pomegranate syrup for a less sweet option)
– Ice
Method
- Start by chilling your cocktail glass. Pop it in the freezer or fill it with ice water while you prep the drink.
- In a cocktail shaker, add:
- 1 oz (30 ml) gin
- 1 oz (30 ml) applejack
- 1 oz (30 ml) lemon juice (fresh is best—it gives the drink a bright, zesty kick)
- ½ oz (15 ml) grenadine
- Fill the shaker with ice and shake well—about 15 seconds or until the shaker feels frosty.
- Dump the ice from your glass (if you used any to chill it), then strain the cocktail into the glass.
Tips & Tricks
– Fresh lemon juice really makes a difference. Bottled just doesn’t have the same brightness.
– If you’re not into overly sweet drinks, start with a little less grenadine. You can always add more.
– Try using a good-quality pomegranate syrup as a more natural alternative to grenadine. It gives you that beautiful color and a deeper flavor.
– Don’t skip chilling your glass—it helps keep the drink crisp and cool longer.
– Want to make this for a group? Just multiply the recipe and mix in a large pitcher. Stir well with ice and strain into glasses when ready to serve.
Make-Ahead Notes
You can mix the gin, applejack, and grenadine ahead of time and store it in the fridge for up to 24 hours. Just add fresh lemon juice and ice when you’re ready to shake and serve.
Storage
Once mixed, the Dempsey is best enjoyed immediately. If you do have leftovers (unlikely!), store them in a sealed jar in the fridge and give it a quick shake with fresh ice before serving again.
Serving Suggestions
A simple lemon twist or a maraschino cherry makes a lovely garnish. The lemon adds a bit more citrus aroma, and the cherry plays up the drink’s fruity side.
I thought I’d share one of my favorite after-dinner pairings too—this cocktail alongside a square of dark chocolate is absolutely dreamy.
What It Tastes Like
The Dempsey has a layered flavor: crisp gin, mellow applejack, tart lemon, and a hint of sweetness from the grenadine. It’s fruity without being sugary, with a gentle bite that gives it a grown-up edge.
Food Pairings
Spicy Starters: The sweet-tart combo cuts right through heat. Try it with buffalo wings, spicy hummus, or jalapeño poppers.
Grilled Seafood: Lemon juice in the drink pairs beautifully with grilled shrimp or scallops. The acidity lifts the smoky flavors.
Chocolate Desserts: The fruity notes in the Dempsey balance out rich chocolate—think flourless chocolate cake or dark chocolate mousse.
Recipe Variations
Winter Dempsey
– Swap lemon juice for orange juice
– Add a pinch of ground cinnamon before shaking
– Warmer, cozier flavor—perfect for colder months
Tropical Dempsey
– Replace grenadine with ½ oz (15 ml) pineapple juice
– Add ¼ oz (7 ml) coconut milk
– Garnish with a pineapple wedge for a beachy twist
Herbal Dempsey
– Muddle a small sprig of rosemary with the lemon juice before adding other ingredients
– Replace applejack with an herbal liqueur like Chartreuse for an earthy spin
Virgin Dempsey (Mocktail)
– 1 oz (30 ml) apple juice
– 1 oz (30 ml) lemon juice
– ½ oz (15 ml) grenadine or pomegranate syrup
– Shake with ice and strain into a chilled glass
Substitution Options
– Applejack: Calvados for a smoother apple flavor, or try brandy or bourbon for a richer twist
– Gin: Vodka works if you want a more neutral base
– Grenadine: Pomegranate syrup, raspberry syrup, or even a touch of honey mixed with warm water
Common Mistakes to Avoid
– Using bottled lemon juice—it dulls the whole drink
– Overdoing the grenadine—it can overpower the balance
– Not shaking long enough—undermixes the flavors and leaves the drink too warm
Q&A
Can I make a batch for a party?
Absolutely! Just multiply the ingredients and mix in a large pitcher. Add ice when serving to keep it chilled.
What’s the best garnish?
A lemon twist or cherry works great. They look pretty and add a little extra flavor.
Can I tone down the sweetness?
Yes—cut back on grenadine or swap it for pomegranate syrup or a splash of unsweetened juice.
Can I make it ahead?
Yes, but leave out the lemon juice until serving time for the freshest flavor.
What’s a good time to serve it?
It’s great for cocktail hour, dinner parties, or even brunch if you’re feeling fancy.
The Dempsey is one of those cocktails that looks beautiful, tastes balanced, and always impresses without being complicated. Whether you’re new to mixing drinks or a seasoned home bartender, this one’s worth keeping in your back pocket.
