T he door opens on a dark, wood-paneled room. What seems like a thousand liquor bottles neatly line the shelves behind the bartender. Smiling patrons relax with cigars in leather chairs or chat with one another over tumblers of whiskey at the bar. In the back, a blues band wails, the singer only a few feet from those who have moved in close and are rocking in time to the music.
This is not the beginning of a 1940s-era movie. This is just a common scene at New Haven bar the Owl Shop. But the establishment’s nostalgic feel is no mistake; it comes from a long history in the Elm City, and its owner’s work to keep that history alive.
Greek immigrant Joseph St. John opened the Owl Shop in 1934. Back then it existed as a bookshop, but beyond the world of literature, St. John had another hobby: mixing and selling tobacco, which he began doing right there in the shop.
Little did he know that his love of tobacco would persist for decades and, eventually, make the Owl Shop a truly unique spot to relax. The bar, acquired by present owner Glen Greenberg in 1998, is one of the only public venues in the state where a person can both smoke and drink.
Because it was historically a tobacco shop, and because Greenberg kept that part of the business intact when he renovated to add a full bar, the Owl Shop wasn’t affected by the smoking ban (enacted in 2004). Under the law, individuals can still smoke in tobacco shops.
So, while other establishments have been smoke-free for eight years now, large ceramic ashtrays—like vestiges from the past—line the bar at the Owl Shop. The air is often hazy with the smoke and mingling aromas from fine cigars and custom-blended pipe tobacco, mixed by in-house tobacconist Joe Lentine. He’s had the job for an incredible 48 years, and makes some of the same tobacco recipes used in St. John’s day.
The atmosphere may turn some newcomers off, especially now that people are used to smoke-free air while imbibing. Yet it’s also the primary reason many newcomers visit the bar in the first place, and why many become regulars—not to mention the 400-square-foot humidor for true aficionados.
“We get people from all different walks of life,” says Greenberg. “The common denominator is the smoking. No egos. They’re just enjoying a cigar and a cocktail and relaxing.”
The non-smoking crowd need not be left out. The Owl Shop is about so much more than tobacco. Their wide range of upscale liquor includes over 150 types of whiskey, a collection Greenberg has personally enjoyed cultivating over the years. Or customers might choose a drink from the rotating wine and craft beer list. Ask a bartender for advice: Greenberg’s staff knows what they’re talking about and their cocktail recommendation (try the Sazerac, trust me) could become your new favorite.
The idea is to offer only “high-end quality products,” says Greenberg, and that idea extends to all aspects of service at the Owl Shop. The menu includes several small plates, all from restaurant and cheese shop Caseus, while bread is from the Chabaso bakery. So when you order an assortment of cured meats, the mixed olive bowl or the brie, pesto and apple Panini, you know it’s going to be local and you know it’s going to be good.
The bar boasts one more, perhaps unexpected, strength: the coffee. Like a true European bar, the Owl Shop offers drinks like the Ristretto (espresso “short and strong”), Cortadito (espresso cut with a splash of steamed milk and micro foam) and the Con Panna (espresso marked with whipped cream).
“My philosophy is, if we’re going to do it, let’s do it right,” says Greenberg. No doubt his clientele are attracted to that philosophy, whether they come in for a cappuccino and cigar at 11 a.m. on a Thursday or lounge late into the night listening to the live blues and jazz music every Tuesday and Wednesday night.
The Owl Shop is capable of being many things to many people, whether they’re looking for a calm café or raucous bar; whether they’re a group of Yale undergrads looking for something new, or clients who’ve been buying their tobacco at the Owl Shop for years and years.
Lentine says he’s had some of the same customers for his entire 48-year stretch, and that their loyalty—and his—is in part due to Greenberg’s efforts to keep the place close to its roots.
Which is to say, it’s still a good place to enjoy a guilty pleasure guiltlessly. And that is a truly old-fashioned feature, a welcome escape from the modern mindset.
The Owl Shop
268 College St, New Haven (map)
Mon-Thurs 10am-1am, Fri-Sat 10am-2am, Sun 12pm-1am
(203) 624-3250 | firstname.lastname@example.org
Written and photographed by Cara McDonough.