Fourth season, second to last or last episode. You may as well jump in now, it's still worth it, as The Wire is the best show on television today, and possibly the best show ever.
However, you need HBO to do so. If you do, it's on whatever your primetime HBO channel is at 10:00 PM EST, and it totally kicks ass.
If you have on demand, watch it in the premium channels-->HBO-->Series--->The Wire section from start to finish.
If you have money, order the first 3 seasons on DVD, or borrow them or something.
If you don't, find some other way.
Apparently, it'll be hopping over to BET, airing from episode 1, January 2007 - which I think will also be the first time an HBO series makes it into syndication on a public channel (not counting sex and the city - I was thinking mainly of good shows). Providing they don't change it or clip anything else, everyone should tune in. I will beat you over the head with a crowbar through the computer if you don't.
EDIT-And the folks at BET deserve some serious props, cuz they clearly have some balls to put it on. The Wire's done fairly poor in terms of viewer numbers despite rave reviews, though those who watch it almost invariably love it. So for a very public and commercial station to take the risk is no little thing. That being said, they may've done it in concert with the possible success in the near future of various bmore rappers like bossman who've been influenced by the show; no idea.