Porchside Pairing: H. Upmann 1844 Añejo with Old Elk Cigar Cut

Another evening of beautiful weather meant another sit on the porch. With no other plans, I dug into the humidor for something on the larger side and landed on the H. Upmann 1844 Añejo Toro. At 6 x 54, it promised a solid couple of hours of enjoyment.

The cigar wears a smooth, oily Ecuadorian Habano wrapper that shimmered in the fading sunlight. Construction was excellent — an even, seamless roll. Beneath the wrapper, a Pennsylvania Broadleaf binder holds filler tobaccos from the Dominican Republic, Honduras, and Nicaragua. This blend, aged for at least five years (as suggested by the name Añejo — Spanish for “old” or “vintage”), promises depth and complexity. Mine had been resting in the humidor about nine weeks, part of the June COTM shipment from Cigar and Pipes.

The smoke opens with rich notes of cocoa, coffee, and mild pepper spice, soon joined by hints of caramel sweetness and a sturdy woodiness. Cedar and pepper weave in and out throughout the long burn, but the profile stays balanced — complex yet approachable, with a satisfying full body. Construction was spot-on, delivering a steady burn and clouds of creamy smoke.

I was so caught up in the cigar that I nearly neglected the pour at my side: Old Elk Cigar Cut bourbon. Typically a celebratory pour for me, it felt right for this leisurely evening.

This bottling was the first “cigar blend” release from Old Elk Distillery in Fort Collins, Colorado. Built on six-year-old bourbons further finished in Sherry, Armagnac, Port, and Cognac casks, it’s bottled at 110.6 proof. On the nose, caramel, vanilla, toasted oak, and spiced fruit draw you in. The palate reveals layers of dark chocolate, toffee, and baking spice, with faint notes of tobacco and leather lingering in the long, warming finish.

Like the cigar, the bourbon is layered and complex. I’ve always found port- and sherry-finished bourbons to pair beautifully with cigars, and the additional cask influences here add even more depth. It remains one of my favorite pours to enjoy with a full-bodied smoke — though it has become increasingly elusive on shelves. Old Elk has also released a Cigar Cut Island Blend, but that one still eludes me.

What more could I ask for? A bold, flavorful cigar, an exceptional pour, the setting sun, and blues floating from the outdoor speaker. A perfect evening.

Cheers!