Cigar Reviews

Olde Penn by Drew Estate, a Famous Smoke Shop Exclusive

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In the summer of 2016, Famous Smoke Shop announced Olde Penn by Drew Estate. Olde Penn pays homage to the old school attitude of “grit and determination” that built Pennsylvania into the state it is today. A little history lesson was given in the press release:

Life in Olde Penn was anything but pedestrian. Its people worked hard, played fair and stood up for what they believed in. When they met adversity face-to-face, they gave it a wry look and spit in its eye. Pennsylvanians business was building America. They followed their fathers into the coal mines, forged America’s railways in their steel mills, tamed the Great Lakes, and 4,600 cigar factories (more than any other state in the Union), plus myriad Keystone State tobacco farms, satisfied the nation’s appetite for a good smoke.

Suffice it to say, Pennsylvania’s roots run deep, hold fast, and remain strong. And it’s in this unanimous, spirited and determined tradition that Olde Penn cigars were forged with the same grit and determination that’s been coursing through Pennsylvanians veins since 1682.

Drew Etsate Olde Penn

Manufactured at La Gran Fabrica Drew Estate in Esteli, Nicaragua, Olde Penn is available in five vitolas: Small Corona (4 1/2 by 33), Robusto (5 by 50), Toro (6 by 52), Lonsdale (7 by 46), and Gordito (6 by 60). The cigar, running between $6 and $7.50 per single, features a Connecticut seed wrapper grown in Ecuador over Nicaraguan binder and filler tobaccos. You can purchase Olde Penn cigars from our good friends over at Famous Smoke Shop HERE.

Drew Etsate Olde Penn



Price: $7.25
Vitola: Toro
Size: 6 by 52
Wrapper: Ecuadorian Connecticut
Binder: Nicaraguan
Filler: Nicaraguan
Smoke Time: 1 Hour and 25 Minutes


Olde Penn by Drew Estate wears a golden tan Ecuadorian Connecticut Shade wrapper. There are mostly small veins to be found on the leaf and a couple of medium sized, stitch-like veins. The light color does little to hide the stretch marks and bumps.

Drew Etsate Olde Penn

A mild aroma of graham cracker and cardboard is found on the wrapper, while big cinnamon and chocolate notes come across on the foot. There is a void in the filler tobaccos near the band and the foot appears under-filled. A shallow, quick cut through the double cap opens up an easy draw. A cinnamon spice instantly warms my palate followed by cedar.

Drew Etsate Olde Penn


Out of the gate, Olde Penn starts with solid mediums flavors. That common Connecticut shade bitterness is being contrasted by a natural tobacco sweetness.  Trailing behind these upfront flavors are earth and a generic woodsiness. As the cigar progresses, a sweet fruit flavors joins in. A significant section of the wrapper is struggling to keep up with the rest of the burn as a dark gray, flaky ash forms. But within no time, the burn has self-corrected 

Drew Etsate Olde Penn


The sweetness has evolved to more caramel-like, making the overall profile richer and there is now a nuttiness to the smoke. The sweetness is keeping the bitterness and earthier flavors at bay. There seems to be a hint of cinnamon spice flavor going in the background as the Olde Penn warms my palate nicely.

Drew Etsate Olde Penn


As I pull into the last third of the Olde Penn Toro, a tear forms in the wrapper as a result of a little too much glue on the band. I can now easily see how thin and delicate this wrapper is. Even with the hole in the wrapper, the cigar is still pumping out smoke and it doesn’t seem to be hindering anything. The central sweetness of the flavors continues to hold strong as a charred wood flavor arrives. The cinnamon spice has departed and the spice at this point is more of the typical black pepper.

Drew Etsate Olde Penn


I have never been a huge fan of Connecticut shade cigars. There are a few out their that get me going, but, overall, they just don’t suit my palate. But when Drew Estate releases a Connecticut shade cigar, I know it is worth a try. I really like the branding and story behind Olde Penn, but more importantly I enjoyed the cigar itself. Olde Penn delivered medium flavors highlighted by a Connecticut shade bitterness and evolving sweetness. This would be a great cigar to pair with a cup of coffee in the morning, but it would also hold its own later in the day on a fresh palate. A couple of construction issues were encountered with the burn and delicate wrapper, but not enough to concern me. There are some great deals on the five-packs over at Famous Smoke Shop and I recommend you grab yourself a couple.

Jeremy Hensley is a bean counter for a non-profit in El Paso, Texas. He is married to the most understanding wife (he still can’t figure out how she puts up with his cigar smoking hobby), and blessed with two beautiful children. When he is not acting like a kid, he enjoys everything outdoors, especially fishing with his dad in the Great Lakes. Also, he meets the criteria of being a Casa Fumando reviewer: being a hockey fan. Feel free to contact Jeremy anytime via email (jmhensley13[at]gmail[dot]com). And make sure to follow him on twitter

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