Ricks & Sticks Pairing Session:

Penelope 10 Year Bourbon × My Father Connecticut

Sometimes a pairing is about interplay — where both elements push and pull against each other to reveal flavors that neither shows on its own. Today’s Ricks & Sticks session brought that dynamic front and center with Penelope 10 Year Bourbon and the My Father Connecticut.

The Bourbon: Penelope 10 Year

Penelope 10 Year opens with a firm oak presence, a touch of char, and a light dried-fruit sweetness reminiscent of raisin. The mid-palate settles into a soft warmth of baking spices, leaving a finish that is structured, calm, and mature.

This bourbon is confident but not loud. Each sip is steady — oak forward, spice-supported, with a subtle sweetness that’s there if you look for it.

The Cigar: My Father Connecticut

Don’t let the Connecticut wrapper fool you. this cigar has My Father depth behind it.

• First third: Heavy cedar up front
• A slow shift into sweet hay and creamy texture

• Light pepper only on the retrohale, staying refined and clean

It’s balanced and composed right from the start.

The Pairing Journey

First Third + Initial Sips

Beginning with the cigar, the cedar is bold. After a sip of Penelope:

• The bourbon’s oak softens noticeably.
• A lighter, sweeter oak tone emerges.
• Even a hint of caramel begins to shine through.

Returning to the cigar, the sweet hay now feels like vanilla, layered into that creamy texture. This is where the pairing sings early: the bourbon gives the cigar a new dimension without overwhelming it.

Second Third

As the cigar transitions, the profile shifts:

• The vanilla/hay fades.
• Earthiness develops more strongly.
• A roasted nuttiness comes through on the retrohale.

Going back to the bourbon now:

• Some of the oak returns to prominence, but
• The baking spices on the finish are more defined and noticeable.

The back-and-forth at this stage becomes more grounding and savory.

Final Third

The cigar loops back, bringing:

• A touch of sweet hay again
• Slight cedar returning on the retrohale

The bourbon remains steady, sweet oak & baking spices, consistent from mid-session onward.

Final Thoughts

This is one of those pairings where the bourbon has a greater influence on the cigar than the cigar has on the bourbon — especially in the first third, where the Penelope introduced that vanilla-cream note into the My Father Connecticut that isn’t typically present on its own.

The cigar changed noticeably across the pairing; the bourbon remained more constant, only shifting in emphasis rather than character.

Overall, this pairing works, not because it’s perfectly balanced, but because it evolves. If you enjoy a pairing where the cigar learns something new from the bourbon, rather than a perfect 50/50 match, this one belongs in your rotation.