The Kentucky Derby: A Cigar Guide

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The Kentucky Derby: Our Essential Cigar Guide 

Sharing the Heritage and Legacy of Pappy Van Winkle

The Kentucky Derby is a celebration of all that represents and honors Kentucky. A horse race full of spectacle and splendor. An event equally as recognized for the event itself as it's signature cocktail - the Mint Julep (made of course, with the next thing that is equally as  synonymous to Kentucky itself as the Derby - bourbon). A months long celebration dedicated to tradition and legacy. Naturally, this is one of our favorite Holidays. 

The Derby is an invitation to enjoy tradition - to celebrate legacy - and to simply celebrate. These are not only our very favorite things - they are what we created Pappy & Company to honor and continue. Of course, we have the food, the drinks and the entertaining down (learn more here), but we also have an equally important component to partaking in this spectacularly iconic event - cigars!

Cigars were enjoyed by our great-grandfather Pappy Van Winkle, so much so that his enduring legacy captured in this image pictures him with a beloved cigar and a drink - understanding the connection between the two to highlight and complement each other and to encourage enjoyment. Naturally, we were compelled to craft a line of signature Pappy Van Winkle cigars in his honor.

The Kentucky Derby happens to be the ideal time to enjoy these two together. Whether you are headed to Churchill Downs or simply relaxing at home to watch who wins the Run for the Roses - we have the ideal cigar to enjoy the occasion. Featuring some of our favorite premium cigars from our core collection, in both barrel-fermented and tradition blends. 

Our Blends: Pappy Van Winkle Barrel-Fermented & Tradition 
Our Pappy Van Winkle Barrel-Fermented cigars are aged in retired Pappy Van Winkle bourbon barrels, infused with signature Pappy Van Winkle flavor notes of chocolate, coffee, cedar and charred wood with an overall smoky sweetness. Our Pappy Van Winkle Barrel-Fermented offerings feature Kentucky Fire-Cured and Nicaraguan filler and a Tapa-Negra-style Kentucky Fire-Cured and barrel-aged wrapper over a base of Mexican San Andres.
Our Pappy Van Winkle inspired Tradition blend, was hand selected by Julian Van Winkle to pair well with your favorite bourbon, with a woody and spicy flavor with notes of ground black pepper, cinnamon and cedar. They feature Dominican Republic and Nicaraguan filler with Ecuadorian Habano Oscuro wrapper.

Both blends are considered medium body and are offered in a variety of vitolas, and a few special limited-releases throughout the year. 

Our Partner: Drew Estate All of our cigars are made in small batches and hand rolled by our partners, master cigar makers, Drew Estate, in Estelí, Nicaragua. Globally recognized for their passion and innovation, they are equally as dedicated to quality and promising a cigar that lives up to both the Pappy Van Winkle and Drew Estate name. 

Kentucky Derby Cigar Guide

Aptly Named: The Churchill

Since sometimes it really is all in the name, or perhaps you are someone who makes their bets based on the name of the horse that they like best. Either way, the moniker of this particular cigar is not only perfect for the occasion, it happens to be a perfectly suited cigar for the occasion. At 7 inches, the Churchill (offered in our Barrel-Fermented and Tradition Blends) the Pappy Van Winkle Barrel-Fermented or Tradition Churchill offers one of the longest smoke times at 60 - 90 minutes, making it an ideal backyard cigar - especially if you are manning the grill for your own Derby brunch or gathering. 

Minutes to Post: The Pappy Van Winkle Barrel-Fermented Robusto

With a smoke time of 45 minutes , the 52 x 5 1/4 Pappy Van Winkle Barrel-Fermented Robusto covers the time between the betting window and waiting to hear those three little words, "and they're off!" As it is light enough for a post lunch smoke, the Robusto is an ideal day time offering for optimal track side enjoyment. Whether that means you are sipping on an ice cold Mint Julep, waiting to see if your long shot bet holds, or just enjoying the spectacle, sights and sounds of Derby Day - the Robusto is the ideal cigar companion. One of our shorter vitolas, it is not lacking in the complexity of smooth flavor. 

Just Here for the Party: Tradition Robusto

Robusto's happen to be the most popular type of cigar worldwide, so we happen to think that makes it a crowd pleaser. Whether you are partaking of the festivities at home, at Churchill Downs, or celebrating with friends - grab a box of our Tradition Robustos to share as you simply enjoy the sights, sounds and flavors of Derby Day. With a 45 minute smoke time, clocking in at 54 x 51/2, the Robusto is an approachable and manageable size to enjoy wherever your Derby festivities take you. While short in stature, it is full of complex flavor. 

The Thrill of Victory OR the Agony of Defeat: Pappy Van Winkle Barrel-Fermented Toro

Turning in a winning ticket or hit an impossibly rare superfecta or trifecta? Or did you only win in the beer line? Either way, the Pappy Van Winkle Barrel-Fermented Toro is considered an all-day cigar - meaning you can enjoy it regardless of your luck at the betting window. at 6 x 52, it promising 45-60 minutes of enjoyment, for beginner to intermediate smokers, enjoyed alongside your favorite celebratory cocktail. It especially pairs nicely with a spicier spirit, such as rye. 

Across the Board: The Tradition Toro

A cigar that is easy to enjoy and is an approachable cigar for beginners to seasoned cigar smokers, the Tradition Toro is an ideal cigar for casual enjoyment. Just like the Across the Board bet that covers your options, the Tradition Toro is a great back-pocket-cigar to enjoy with anyone on Derby Day for 45-60 minutes of relaxed, Pappy Hour style enjoyment. Designed to be savored slowly, the Toro makes an excellent cigar for a Kentucky Derby celebration that will last all day long.