“How we doin’ today?” a voice calls out from the back.
“I am well.” I reply as I get my first glimpse of the person whose voice I heard.
From behind a case full of Padrons rambles a man with white hair and beard, a bow-tie, suspenders, aided by a walking stick. “Have you been here before?” he asks.
“Yeah, once. Last year.” I answered.
Without missing a beat, he retorts, “Well, stop being such a stranger and come in more often!”
I respond with “I would, but it’d be a heckuva commute. I’m not exactly from around here.”
“Where ya from?” he asked.
I tell him I hail from the Midwest and he immediately guesses Wisconsin, and when I said Minnesota he replied with something like “Well, neighbors then.”
He goes on to tell me that he had a gent in the shop last week from my cheesy neighbor state to the east and how this particular gentleman is a Winston Churchill impersonator; he travels the country doing speaking engagements as Winston Churchill. My bearded host proclaims that “there must be a god” because our World War II-era English Prime Minister impersonator gets to write off all of his cigar purchases. I chuckle and agree.
This was my first two minutes inside Federal Cigar in Portsmouth, New Hampshire, the third oldest city in the United States. The tobacco shop itself is not the largest I’ve ever visited; we’ll call it on the cozy side. Upon entering, there’s a cashier desk to the left and two long rows of cigar shelving. On the right wall, there is an assortment of pipes. As you make your way to the back, you’d notice a door leading to a downward staircase
and an exit door along the left wall. This is because the tobacco shop closes somewhat early (7 pm most nights) but the lounge stays open till 11 or later. If you were to wander outside the shop, which sits on the corner of Market and Ladd Streets, you would find a nondescript door which leads beneath the streets of Portsmouth into one of the coolest smoking lounges I’ve ever had the pleasure of visiting.
As you open the door and step into the lounge area, you will see a wall lined with plush leather booths and tables; the granite bar sits opposite these booths. Upon walking a little further, you’ll notice another room with a ‘Members Only’ sign hanging above it. There are lockers available for cigar storage and other typical member perks. The place was somewhat dimly lit, but that contributed to the overall vibe of the joint. There are a couple TVs behind the bar and if it weren’t for that and a few other modernizations, you’d think you were sitting in a speakeasy from the Prohibition era.
I ponied up to the bar and was greeted almost immediately. Having never smoked in this lounge, I took a minute to peruse the menu which contained a very impressive selection of whiskeys and cocktails. I made my choice, struck a match, and lit my cigar. It didn’t take me long to realize that every other person in the lounge was very much a regular visitor. The barkeep called everyone by name and knew their drink orders. I commented on this to the gentleman sitting nearest me and he solidified my notion that this was the place to smoke.
The fact that it was midweek and only 7 pm didn’t hurt. Apparently the lounge is very popular with out of town businessmen and vacationers and can be fairly packed most weekends. The bar area does have a smaller humidor with cigars available for purchase if you don’t make it to the store in time. However, the selection is quite a bit smaller. The lounge also boasts a terrific ventilation system. No low hanging clouds of smoke to cough your way through.
“How do you like that cigar?” I turn to see my bearded friend from the above retail space. He had introduced himself as OFWB (Old F*ck With Bowtie) AKA Gary but “nobody remembers the name Gary; they always remember the guy with the bowtie though.” I greet him by his ‘unmemorable’ name and tell him his cigar recommendation has been great. He joins me in sitting at the bar and, after receiving his pinot noir, we begin chatting about his decade in the cigar business and the history of this particular shop. He points to the beams in the ceiling and tells me to look closely so I could see the hand-hewn marks in the wood.
The building has been around for over 200 years. Nowhere else in the United States I can think of can you smoke in a building that old. The business itself will be celebrating it’s centennial in two years. That’s right, Federal Cigar was started in 1921 and has been in business ever since. Before that, a place called United Tobacco began in 1904 but was renamed Federal a year into Prohibition. Gary and I chat the rest of the way through his glass of red. We cover everything from exotic places we’ve visited to our mutual interest in World War II. It’s guys like Gary that make smoking in a lounge something you won’t forget. His knowledge of the product and his wit and dry sense of humor is something I appreciated a great deal.
I very much enjoyed my time at Federal Cigar. Whenever I find myself anywhere near this charming city on the east coast, I will definitely try to visit again.
(Multiple attempts were made by HBTC to contact the shop owners for permission to include pictures from their website. HBTC did not receive a response so we just published the pictures taken by Andrew during his visit. If we ever do receive permission from Federal Cigar ownership to use their photographs, we will add those to the article.)