Penelope Cigar Sessions Chapter 01 Review

Distillery: Distilled in Lawrenceburg, Indiana—Presumably MGP

Proof: 101.0 (50.5% ABV)

Age: Six Years

Mashbill: 72% Corn, 15% Rye, 13% Malted Barley

MSRP: $80

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Focus.  Finess.  Familiar.

Penelope Bourbon has carved its niche in nontraditional blending—often combining whiskey types to go beyond the standard bourbon template.  Cigar Sessions Chapter 01 follows in that mindset, bringing together straight bourbon, American light whiskey and American single malt into a blend aimed squarely at, as the name suggests, cigar pairings. 

Chapter 01 marks the start of a new series from Penelope that leans into purpose-driven releases, using blending to tailor the drinking experience.  While it carries no age statement, the whiskey includes barrels aged up to six years.

While I’m not a cigar smoker myself, this release is reportedly engineered for those who are.  For whiskey drinkers, the real question is whether the blend delivers enough structure to stand on its own.  Let’s take a closer look.

Penelope Cigar Sessions Chapter 01 Review: Tasting Notes

Nose – 4.2/5

Milk chocolate.  Whoppers malted milk ball.  Nutmeg.  Red apple.
Strengths:  Creamy cocoa notes lead and is supported by rich confectionery-like sweetness.  Gentle spice.
Why It’s Not Higher:  Slight grainy or seemingly youthful note beneath the surface keeps it just shy of fully polished.
Rating Justification: Strong and inviting, though a bit restrained; a solid high-barrel strength nose.

Palate – 3.9/5

Chocolate.  Tobacco.  Honey.  Almond butter.  Cinnamon.
Strengths:  Deep cocoa foundation carries forward from the Nose.  Subtle savory tobacco.  Honey and nutty notes are nuanced.
Why It’s Not Higher:  The mid-Palate feels light and slightly grainy.  There is less weight than might be expected at its proof and age.
Rating Justification:  Pleasing complex.  A controlled sweetness that’s enjoyable.  Lacks in the mid-Palate.

Finish – 4/5

Light oak.   Honey Nut Cheerios.  Graham cracker.  Light cinnamon heat.
Strengths:  Long, evolving Finish.  Toasted confectionary notes linger pleasantly.  An embrace from the warmth of the proof.
Why It’s Not Higher:  Flavor fades a bit too quickly mid-Finish before warmth returns.
Rating Justification:  Finish redeems the Palate.  Richness that does what it aims to do–cigar-pairing-friendly.

Value – 4.8/5

Strengths:  Blending that achieves the cigar-friendly profile.  Emphasizes chocolate, mild spice, and toasted sweetness.  Inclusion of American light whiskey and single malt sets it apart from traditional bourbon blends.

Why It’s Not Higher:  At $80, the complexity falls slightly short of similarly priced whiskeys.  Mid-Palate lacks some depth.  Finish—while pleasant—is not especially long or layered.  As a standalone pour, it doesn’t quite match the richness or structure of other whiskeys in this price point.

Rating Justification:  The Value here comes from concept and intention more than age or proof.  For those seeking a more traditional bourbon profile, it may feel slightly overpriced.

Penelope Cigar Sessions Chapter 01 Review: The Verdict

Penelope Cigar Sessions Chapter 01 succeeds in its aim:  offer a whiskey that complements a cigar without overwhelming the experience.  

What stands out here isn’t the age or high proof—it’s the intentionality of the blend.  For fans of Penelope’s blending style, this delivers a very good pour.  But for those evaluating purely on impact per dollar, the lighter structure and shorter Finish almost holds it back from Gold-tier territory.

Verdict – 4.1/5

We score each bourbon based on nose, palate, finish, and value.

Scoring System:

• Platinum – 4.5 – 5
• Gold – 4 – 4.5
• Silver – 3 – 4
• Bronze – <3