When I first started doing media outreach for Rocky, it meant finding a reason a show was a special event (as opposed to "that thing we do every week" - not newsworthy), calling the local newspapers and maybe writing a press release.
In college the special event was usually a once-a-year college show in October; I'd call the local papers and usually get an interview (maybe even a photographer) from the campus paper, for whom the hook was "local college students do [insert activity here]". We were in college; we had funny costumes; and we had a couple of talking points about the history of Rocky, how much fun it was, and that people should come see the show. If we were really on the ball, we'd contact the local community calendar, brand ourselves as an "amateur theatrical group" (true, if perhaps not quite what they were thinking) and plug our college show there. This was supplemented with getting paper flyers approved for campus posting (as a college-based amateur theatrical group) and also leaving them in the usual likely locations - bars and other college hangouts.
Once I was out in the world, the college papers were no longer interested. However, the same basic formula applied. A cast I was with was doing a charity event, so I looked up the local papers, called them, and found out where to email a press release. Which was easier now as I could find examples on-line instead of having to look up how to write a press release in a book. I'm still using the press release I wrote for that event as my basic template.
It was a relief to realize recently that press releases still work; the local papers appear to be mostly on-line now, but a recent special event (another charity event) got play on-line, anyway, and netted us the #1 or #2 spot for Google search "Rocky Horror" + charity.
Whether or not our target audience reads the papers is another matter entirely. But I'm not writing about how to set up your Twitter/Facebook/webpage; I'm hoping you have that (and flyering) covered. So here's how this works. I'm not including how to contact local radio or TV stations - I've never tried it, though I probably should (maybe next year).
1) Write your press release. I'm not going to go into detail about that; you can Google how to write one (though if you'd like a sample of one that worked for me, I'd be happy to share).
2) Find some places to send it. We used to get a local free community weekly; I'd have submitted the release there, but they got bought by the Chicago Tribune (not local). A quick search led me to http://www.usnpl.com/ilnews.php . This lists all the newspapers in Illinois (and the other 50 states), with phone, Twitter, Facebook and webpage information. From there it was fairly easy to find out where to submit items (look at the bottom of the webpage, generally) and who to call (with questions about where to send a press release, and to ask about submitting photos).
Patch.com is also helpful; they're not in all the states yet, but they're in about half of them. Patch features local news and lets you (after creating an account) upload local news. That #2 result on Google is due to an article I posted on Patch.
3) If you can submit articles (aka provide the newspaper with free content), do so. Distill down the who/what/when/where from your press release and upload a photo. Hit up Patch or other local sites as well.
4) Contact the papers and talk with a real human being if you can. (If you can talk with the Local News or Features editor, do so. If not, ask who that person would be and get the name/contact info for them.) If you send your press release to a person instead of a generic email address, your chances of getting picked up are better.
5) Consider providing photos. A story with photos will get more traction.
It's still not easy to get a photographer. If you can, or if they offer and you can make it happen, go for it - they probably have a better camera than you do. But it's pretty easy to take at least passable photos these days, and sending digital photos is easy. Shoot in high resolution and keep photos at least 300 dpi. These guidelines are from my old print days - the newspapers just said "so long as they're big, and appropriate for a family paper." This is easier the second year - most of our photos were from the previous year's event.
As far as timing, the local papers tend to work on a weekly schedule. They weren't really interested in us until about 2-3 weeks before the event.
We got great Google placement from Patch (which we then were able to plug on Facebook and Twitter); an interview with a local paper, printed with a photo we provided (that we're not sure anybody read on paper, but it showed up on their on-line version); and placement on a "Fitness events" calendar (since our event was a charity walk), printed with a big photo from the photo shoot that we put together 3 weeks before our event.