Cigar Buying Guides

5 Great Cigars to Pair with Your Favorite Halloween Candy


Updated October 2022

BOO! IT’S THAT TIME OF YEAR again when children dress-up in every manner of Halloween scary to collect bags of free candy. It’s a fun holiday, and I always look forward to seeing what costumes the kids come up with every year. Yet, what I look forward to most is the leftover Halloween candy. And have you noticed how the candy gets smaller every year? What’s up with that?

Come to think of it, what if in some bizarre parallel universe adults prowled their neighborhoods on Halloween night for cigars? Wouldn’t that be a sight. Can you imagine seeing people dressed like Carlito Fuente in full guayabera regalia, or Jonathan Drew in Hip Hop chic, the late Avo Uvezian in his classic white linen suit and Stetson, or even someone sauntering down the street on a horse as Litto Gomez? I’ve got others, but…

Before I digress too far, there is one thing Halloween and premium cigars actually do have in common—the candy angle. Yes, candy and cigars share a number of similar flavors, depending on the blend of course. I’m not talking chocolate or berry flavored infused cigars, I’m talking about traditional, premium hand rolled cigars made with tobaccos that naturally evoke notes of chocolate, nuts, fruit, cinnamon and other candy-like notes. So, what follows are five wickedly luscious cigars. Even if they don’t taste like some of the popular Halloween candies note-for-note, they will certainly complement them. So, pair ‘em up!

Montecristo Espada Ricasso

Espada by Montecristo is the first of three blends all crafted by the famed Grupo de Maestros with Plasencia-grown Nicaraguan tobaccos. The 5”x54 Montecristo Espada Ricasso is a medium-full puro with fillers from Jalapa, Ometepe, and Condega surrounded by a flawless 2010-vintage Jalapa wrapper. Creamy flavors of sweet cedar, cocoa, coffee, nuts, cinnamon, and more make this cigar a flavor bomb of delectable assets. For the wide berth of flavors in this cigar, Reese’s Peanut Butter Cups® would make an excellent pairing with this cigar.

Padrón 1964 Anniversary Imperial

Padrón Cigars have often been described as having base notes of coffee and cocoa. If you’re a regular Padrón smoker, surely you’ve noticed this by now. Their 1964 Anniversary line serves up a more refined course and the 93-rated, 6”x54 Imperial is a great example. Blended with their most prized Nicaraguan tobaccos, leather, coffee bean, cocoa and mocha are just some of the more standout flavors in this perfectly-balanced medium-bodied cigar. With its mocha and chocolate flavors, a Kit Kat Duo® would be a nice match for this classic.

Plasencia Cosecha 149 Azacualpa

Like the Montecristo Espada above, Plasencia-grown tobaccos make this latest Cosecha a sweet sensation. However, this puro is all-Honduran starring an Olancho San Agustín wrapper, Jamastran binder, and Jamastran, Olancho, and Talanga fillers. The 6”x52, Cosecha 149 Azacualpa (ah-zah-kwal-pah)—say that five times fast—is medium full in body and loaded with well-balanced goodies. Light pepper simmers on the sidelines while cream, leather, wood, baking spices, and dark chocolate melt on your palate. A Milky Way Midnight Dark® will definitely do nicely with this toothsome Toro.

Sancho Panza Double Maduro Robusto

Sancho Panza is one of those brands that seems to fly under the radar. Yet, the re-blending the brand got this year, which included input from Room 101’s Matt Booth, should get some long overdue attention. A sun grown Ecuadorian Sumatra wrapper, Nicaraguan Esteli binder, and Dominican and Nicaraguan fillers set the table for this smooth, medium-bodied smoke. Opening with notes of espresso, the smoke leisurely transitions to leather and nutmeg, culminating in semi-sweet chocolate. Hard to put down, I think a Mounds® bar would easily complement this uber-sweet tobacco treat.

Dunbarton Tobacco & Trust Sobremesa Brulee Toro

About as smooth, creamy, and luxurious as it gets. This mellow to medium line extension from Dunbarton Tobacco & Trust is among my personal favorites for its uber creamy and naturally sweet smoke. Even the aroma is sweet. A bitter-free Ecuador Connecticut wrapper, bale-aged for three years, sits atop a naturally sweet Mexican San Andres Negro binder over Nicaraguan fillers. Cedar, caramel, coffee, and a spot of cream and sugar make up the base notes for this Toro, while flourishes of vanilla and hazelnut occasionally wind their way into the mix. For its outstanding creaminess, a 3 Musketeers® bar would be my best-bet for pairing in this case.

Bonus Track: Drew Estate Tabak Especial Dulce Lonsdale

You’ve just witnessed five almost candy-like cigars, all of which are made traditionally with non-flavored or infused tobaccos. So, for those of you who really do like “flavored” cigars, I’m adding this 6¾” x 44 Tabak Dulce Lonsdale. As someone who prefers coffee-infused smokes, I feel this particular vitola is among the best out there. The blend consists of a creamy Connecticut wrapper, Sumatra binder, and rich Nicaraguan fillers infused with top-grade Nicaraguan coffee for “the perfect nuance of luscious espresso.” Since coffee flavor is the main ingredient, a Snickers® bar will add some nice peanut, caramel, and chocolate to this espresso laced Lonsdale.

I hope you found these Halloween candy pairings worthwhile and discovered some excellent cigars you may have missed. For those who have a sweet tooth some of them might be a bit over the top. However, when you think about it, just about any sweet treat goes well with a fine premium cigar. I sometimes prefer almonds and dark chocolate with my cigars. If you’ve got some additional pairings, please leave a comment.

Milky Way, 3 Musketeers, and Snickers are registered trademarks of Mars Inc.Mounds and Reese’s Peanut Butter Cups are registered trademarks of Hershey Chocolate & Confectionery LLC.