Cigar Shenanigans Cigar & Cocktail Lounge — Attraction in Conway

There's something deeply American about driving through New Hampshire's White Mountains to find yourself in a place that shouldn't exist—yet absolutely must. Cigar Shenanigans occupies that strange territory between guilty pleasure and genuine craft, where a college professor and a Culinary Institute chef have created something that defies every preconception about what a cigar lounge should be.

The first contradiction hits immediately: this is a temple to tobacco wrapped in the aesthetic of your buddy's finished basement. Knotty pine everywhere, leather recliners that have seen some life, and a wall-to-wall collage of cigar bands that looks like the world's most expensive decoupage project. It should feel ridiculous. Instead, it feels honest.

Penny Piva, the professor-turned-proprietor, greets newcomers with the enthusiasm of someone genuinely thrilled you've wandered into her living room. She'll walk you through their humidor—20,000 cigars maintained with Swiss precision—explaining the difference between a Sobremesa Brulee and a Liga Privada with the same passion she once brought to lecture halls. This isn't performance; it's evangelism.

The second paradox is more troubling: how do you reconcile genuine hospitality with an industry built on products that will, quite literally, kill you? Here's a place where the ventilation system works so well that your non-smoking companion won't leave reeking of tobacco, where every detail screams "we care about your comfort"—while you're engaged in an activity that definitively doesn't care about your health.

Yet watching a regular select an Herrera Esteli with chess master deliberation, sipping Woodford Reserve while discussing Dostoyevsky—there's something undeniably civilized about the ritual. The harm is acknowledged, weighed against pleasure, and consciously accepted. It's refreshingly adult in an increasingly infantilized culture.

The third tension is perhaps most fascinating: gender dynamics in America's most masculine leisure pursuit. Traditional cigar culture reeks of exclusion—leather-bound boys' clubs where women exist only in oil paintings. Cigar Shenanigans flips this script without fanfare. Female staff navigate the humidor with expert authority, couples share selection advice, and nothing screams "we're breaking barriers." Expertise and hospitality trump machismo.

Perhaps that's the real magic trick Penny and Valentino have pulled off. In an era when authenticity is increasingly manufactured, they've created something genuinely unpretentious. The $879,000 annual revenue suggests others agree. The regular who brings his German Rottweiler (yes, they're pet-friendly) for Sunday sessions isn't performing wealth—he's just enjoying excellent tobacco and honest conversation.

This is comfort food for the soul, if comfort food came wrapped in Connecticut Broadleaf and paired with small-batch bourbon. The contradictions should collapse under their own weight. Instead, they create something rare: a place that respects both tradition and evolution, acknowledges vice while celebrating craft, welcomes everyone while maintaining standards.

In New Hampshire's Live Free or Die landscape, Cigar Shenanigans offers a third option: live consciously, with genuine pleasure and honest company. Sometimes that's...

First time....Service at the bar was just barely ok, if I return will be much more descerning with gratuity commenserate with the level and the delivery of customer service. Bourbon and Brandy selection needs a definite upgrade... a dial down on the bartender surliness its not a good look. Was apparent the job of bar-tender and "tending to" wasn't occuring during my patronage of the establishment. Seeing other customers wondering when the sole bartenders social hour will end to "get around to" seeing if anyone...other than their friends need anything.... bar was basically empty... so not an arduous task by any means. Not a big ask when that's the job. Having patronized some pretty classy cigar bars around the world that didn't have an eighth of the superiority complex I ran into. It's a turn off, not the "vibe" you want to project. It's just cigars, the service before, during, and after gives the swagger, the key with swagger is not the choke your patrons with it. Might want to dial it back and be more aware how you're coming off too customers... we dont know you; you dont know us. Patrons keep the lights on. That was my take away impression/experience as a first time patron. Selection of cigars was very nice. The only bright spot... the young man assisting me with my selection, he was nice, personable, friendly, knowledgeable and, professional. Sadly, It went downhill from there. A better review would have happened if I exited afterward....I didn't. The other areas where people linger in, to hang out, and spend more money in and enjoy their cigar needs "adjusting". It's a business and service needs some polish so its less abrasive. Cigars get them in the door, the experience you walk away with after defines the odds of a walking back in again. Something...

TLDR: Fantastic. A must visit for your trip to North Conway.

Owners Penny and Tino make this lounge a wonderful and welcoming place to visit. A massive collection of cigars and great drinks to pair with them. Relaxing environment with top of the line air filtration, so no smokey clouds looming over the guests. Lounge in comfort in one of several seating areas or at the bar. Shawn, usually found at the bar can make all manner of drinks from mixes to espresso. The espresso martini is especially good. A members club offers several packages for the cigar fan. Either get the monthly sampler with 4-7 cigars wonderfully selected by Penny and sent to you home or saved for you at the lounge. Or maybe you are a local and would like your own personal humidor locker to keep you cigars fresh and at the ready each visit. The back area sports a fireplace and patio deck. A cabinet of board and card games is available along with card tables and chips to keep you entertained. Several TVs at different locations with the customer able to choose the show. I make a point to visit Cigar Shenanigans every time I'm in North Conway. It feels like home every time I walk in the door. I invite anyone looking to relax your day away to visit here. Open 7 days a week and as late as 1:00 am. One last thing, this Lounge is dog friendly. If you have the family pup, don't leave him in the car, have him come in...