The Monterey Pub is one of the few pubs in Pittsburgh that really deserves the name. It's a friendly neighborhood place that places as much importance on good food and conversation as on drinking.
The menu here is fantastic, with a tendency towards Irish food with a slight twist. The Guinness pot roast is always good, and I'm partial to the ploughman's lunch (although the ploughman's is not the real thing -- it's missing the Branston Pickle!). The beer selection isn't as great, tending towards macro brews. Finally, the atmosphere is fantastic -- a great place to have dinner with some friends, in the middle of the beautiful woodwork and nice decorations. This isn't the place to go watch a game, though -- there are a couple TVs mounted above the bar, but it's really more of a place for dinner and chatting than Steelers-ogling.