Where to Smoke: The Owl Shop, New Haven, Connecticut

Where to Smoke: The Owl Shop, New Haven, Connecticut
The Owl Shop has been serving tobacco products since 1937.

Walk into The Owl Shop in New Haven and smile: Inside is everything you want in a cigar bar.

Cigar selection? The walls to your right are lined with all manner of precious goods, from Padrón Family Reserve 50 Years to the latest La Aroma de Cuba from the folks at Ashton. Spirits? The long bar to your left overflows with booze, from Scotch to Bourbon to Cognac and rye. Setting? Comfy leather chairs in the back, cocktail seating in the front, tin ceiling above.

I sit in the front at a table custom made for cigar smokers. An elongated, ultra-wide, silver-hued ashtray rests into an opening cut into the table, with multiple rests ready to hold your cigar. I take out my cigar case, removing an ultra-fat torpedo squared off in a pristine trunk pressing. I order a High West Rye Manhattan, up, and when my server brings the icy cocktail to my table she eyes the cigar with a knowing look.

"Is that the Eye of the Shark?" she inquires. She is correct. The rare Fuente smoke is not yet in stock at the Owl, but she has been reading up on new releases and was eager to discuss the smoke.


The Owl Shop would be golden even without the added bonus of such well-informed servers. It has been serving tobacco products on College Street since 1937. Originally owned by the St. John family, in 1998 it was acquired by Glen Greenberg. Greenberg turned the cigar shop into a full-fledged cigar bar, acquiring a liquor license and changing the look from rustic to luxurious. When Connecticut instituted a smoking ban in 2004, the Owl had something others could not replicate—serving drinks and allowing cigar smoking under the same roof. The Owl was grandfathered in as a true cigar bar.

The Owl lost a fixture in February when Joe Lentine died. Lentine, who was 70, had worked at the shop since the 1960s, spending some five decades behind the counter. His specialty was mixing custom blends of pipe tobacco. Today, there's a photograph of Lentine across from the bar so he can still spend time in the shop he so adored.

The Owl Shop is located near the grounds of Yale University, in the heart of New Haven. Theaters, fine restaurants and hotels are only steps away. The sidewalks are often busy with foot traffic: students walking between classes, professors ambling, tourists seeking out the latest place to dine. For those in the know, the Owl is a superb place to end or begin your night in New Haven with a fine cigar and a proper cocktail.

The Owl Shop
268 College Street
New Haven, Connecticut 06510
(203) 624-3250

Monday: 10 a.m. to 1 a.m.
Tuesday through Thursday: 10 a.m. to 1 a.m.
Friday & Satuday: 10 a.m. to 2 a.m.
Sunday: Noon to 1 a.m.


"Quite a change from the Owl Shop I visited to buy a pipe back in 1969. I love what it looks like and offers now. Next time I come to Connecticut to visit my family, I will have to take time to see the new Owl Shop - and probably have a drink and a cigar. Wayne Freeman" —March 8, 2016 16:45 PM