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Top Five Cocktails for the Kentucky Derby

The Kentucky Derby, which has its major showdown at Churchill Downs on Saturday, is the prime opportunity for us all to step into the role of Southern gentry for an afternoon. The ideal derby celebration involves seersucker and bowties, wrap dresses and hats with feathers – and maybe something about a horse race. But by far the most important aspect is the booze. Here's a list of cocktails around town that will make you feel like the mannered class we know you are:

1. The Concord Grape Mint Julep at Tipsy Parson Rule: Any self-respecting Derby reveler needs to consume at least one julep during festivities. While the classic Mint Julep combines Kentucky’s finest – bourbon (always bourbon) - with muddled mint and simple syrup, you can try a whimsical variation at Chelsea’s Tipsy Parson. The concord grape adds a tangy note, and there’s no arguing that it’s one of the prettiest cocktails in creation -- it even made the cover of the venerable Garden and Gun magazine.

2. The Bourbon Bloody Mary at Char No. 4 In general, the signal you send with any Bloody Mary in your hand is that of sophisticated abandon -- “I’m drinking when I could be sleeping.” At Char No. 4, the Carroll Gardens temple to pork and brown liquor, they give their vegetable juice a distinctly sweet flavor of the South.

Bourbon Bloody Mary

3. The Pimm's Cup at Schiller’s Liquor Bar Bourbon is the de facto Derby liquor, but we’ll make an exception for this little goblet of springtime. At Schiller's Liquor Bar, they make their cups with a pour of Pimm's -- a fruity gin liquor -- along with a veritable garden of cucumbers and citrus. Pimms Cups are a traditionally British drink, so they’re perfect for drinking barefoot on a lawn.

Pimm's Cup

4. The Back Forty at Back Forty The third bourbon option on our list is the simplest: Bourbon, citrus, maple syrup. The Back 40 is served at this East Village gem, which is named after the number of seats in its garden backyard. It’s made for luxuriating in a backyard, and it has the perfect degree of complexity for serving in batches.

The Back Forty

5. Matt’s Ginger Old-Fashioned at Brooklyn Social If the amount of fruits and vegetables presented in the previous slides is a little too precious for you, dear drinker, you can always embrace an old friend. This bourbon drink is an updated classic – it’s got bourbon, ginger, sugar, cherries, orange, bitters and soda. A standard with gentility.

Matt's Ginger Old-Fashioned