Leaf by Oscar

Leaf by Oscar has been part of the Pittsburgh cigar scene since 2003, and the word around town is that this is one of the better spots in the city to sit down with a good smoke. The cigar selection draws the most praise, from the shop's own Leaf by Oscar sticks to Island Jim and Big Johnny. Locals will tell you the Leaf by Oscar Maduro and the Corojo leaf-wrapped cigars are the ones to try first. One regular called his an easy pull, long lasting, and smooth with a hint of sweetness, the kind of stick that turns a single purchase into a whole pack.

Ask anyone who hangs out here and the atmosphere comes up fast. People love the decor, the live music that turns an evening into something worth sticking around for, and the coffee, which folks rave about nearly as much as the cigars. The staff has a reputation for being fun and genuinely helpful, so if you are new to the shop or just looking for a recommendation, you will not be left standing around guessing. The reach of this place is bigger than you would expect.

We have heard from people who tracked down Leaf by Oscar cigars as far away as Asheville and even Australia and Canada, then came looking for the source. That kind of word of mouth says a lot. Along with the cigars, they carry smoking accessories to round things out. Not every experience has been flawless.

One person came away disappointed after a cigar that wouldn't stay lit, but that's the exception among a run of high praise. If you are in Pittsburgh and want a cigar shop with real character, easy company, and a strong local following, Leaf by Oscar is well worth a stop.