When I moved to Pittsburgh from out of state a few years ago, I did so with some trepidation. Let's just say the Steel City's reputation for substandard restaurants precedes it, and living under the totalitarian thumb of the commonwealth's infamous Liquor Control Board does nothing to dispel that image. I was pretty sure I was moving to one of the most food-and-wine-challenged cities in the country.
Happily, I can say that the restaurant scene is far better than reported — certainly not outstanding, but decent, earnest and improving, with some real gems scattered around, like Legume and Alla Famiglia (both, not coincidentally, BYOB establishments). I can't say the same for wine lists around the city, most of which are grossly overpriced (thanks in large part to an onerous state and local tax system) and pretty uninspired to boot — even in some of the city's more esteemed restaurants. And actual proper wine service ... is exceedingly rare.
A few places that are fighting the good fight — and feel free to add to this, fellow 'burghers:
Mio in Aspinwall. Terrific list, terrific menu, terrific service. And, brother, do you pay for it. Still, if you're looking to impress someone visiting from San Francisco or NYC, Mio sets the standard.
Enrico's in Shadyside. The food here I've found to be somewhat inconsistent, but the all-Italian varietal list (where else can you get a Gattinara or Cannonau by the glass?) is always a pleasure with a nice balance between by-the-glass and by-the-bottle offerings. (Also a good grappa selection.) Eric, the bar manager/sommelier is very knowledgeable and gregarious.
Silk Elephant in Squirrel Hill. Again, the food at this Thai-tapas fusion joint is hit or miss, but the wine list is expansive, innovative (Petit Verdot with that lamb curry? Absolutely.) and refreshingly QPR-focused. Their sommelier, Jamie (as far as I know, Pittsburgh's only female som), is a terrific asset: knowledgeable, friendly and down-to-earth.
I'll add more as I encounter them, but in the meantime, I hope other Pittsburgh chowhounds do the same. What restaurants have your favorite wine lists in the 'burgh?