Cigar and Bourbon Pairing Guide: Louisville’s Best Combinations

Louisville calls itself Bourbonville for a reason, and here in Jeffersonville — just a mile across the river — we’ve spent years figuring out which cigars actually stand up to a proper pour. Pairing isn’t about matching strength for strength; it’s about finding flavors that lift each other.

Padron 1964 Anniversario + Elijah Craig 12 Year

The Padron’s cocoa and leather notes meet the Elijah Craig’s vanilla and oak. Neither overpowers the other — this is the pairing we recommend most to first-timers.

Arturo Fuente Hemingway + Woodford Reserve Double Oaked

A milder cigar deserves a gentler bourbon. The Double Oaked’s caramel sweetness complements the Hemingway’s cedar and cream without fighting for attention.

Drew Estate Liga Privada #9 + Four Roses Small Batch

Liga Privada is a full-bodied, earthy smoke — it needs a bourbon with some spice to match it. Four Roses Small Batch brings just enough heat to keep pace.

RoMa Craft Cro-Magnon + Buffalo Trace

A classic, no-frills pairing. Cro-Magnon’s pepper and char sit well against Buffalo Trace’s caramel backbone — simple, dependable, always good.

Come try any of these pairings in person at Riverside Cigar Shop & Lounge — we pour the bourbon, you bring the conversation. Not sure where to start? Ask any of our staff; that’s what we’re here for.