Step back in time at the Nat Sherman Townhouse, the family-owned business where big shots like Frank Sinatra and Rudy Giuliani have gotten their cigars for decades


cigarettes, cigars, smoke shop, Nat Sherman 2444

Sarah Jacobs

Nat Sherman is celebrating its 85th anniversary this year.


In the midst of Midtown Manhattan's modern hubbub, you might stumble upon a place that's a step back to an entirely different time. It's the Nat Sherman Townhouse - just a few blocks from Grand Central Terminal - and it harkens back to an era when tobacco was king, business was conducted over an ashtray, and everyone wore a suit.

Celebrating 85 years in operation this year, the family-owned-and-operated Nat Sherman brand has weathered the trends of decades to remain the preeminent American brand of cigars. The townhouse itself has been a favorite hangout of everyone from Frank Sinatra to former mayor Rudy Giuliani.

Inside the smoke-filled parlor, you'll find an eclectic mix of patrons, antiques, and distinctive tobacco products. Take a tour back in time with us, below.