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A legitimate contest is almost always free to enter. There are a few legitimate contests with fees, but most of these are professional-level. Read carefully to find out who the sponsor of the contest is, and do some research if needed to find out if it's a real organization. To name two which sponsor contests for calendar photos, Amtrak and Union Pacific are clearly legitimate. So are contests from established publishers such as Kalmbach.
If you've not heard of the place, and can't find out about it, it could be a certificate mill (like a diploma mill, a place where you just pay to get a meaningless piece of paper). Remember that anyone can call anything "prestigious" or "famous," even if the status only exists in their own mind. Don't be taken in by names. I once crossed paths with a man who talked about how his photos were on display in a certain gallery, and the name sounded important. But I'd never heard of the gallery - it turns out that it was the name he affixed to his studio wall. Beyond his attempt to inflate his prices, he wasn't ripping anyone off, but not everyone is so innocuous.
Identity theft schemes abound, and caution should be used when responding to contests, as is the case with any solicitation. A less-than-honest contest could be a ploy to steal your photo (check the fine print, if sign over the copyright by entering, it's no longer yours, no matter what) or an effort to gain information to steal your identity, or maybe both. You should only have to submit name, contact information, and something about the photo or your status as a photographer. If you win, it's legitimate for the sponsor to ask for a tax identification (such as your social security number)--a good reason to make sure that the sponsor is legitimate.
It's important to look at the fine print and see what rights the sponsor wants to use your photo. It is common for a contest to require that you allow the sponsor to use your photo if it wins - in effect, the prize is your payment. Fair enough, but some sponsors want exclusive and unlimited use forever, so that you can't even print a copy yourself! Others will pay for use beyond the direct purpose of the contest. Be careful of contests which claim the right to unlimited use of any photo submitted, without paying you at all - even if you don't win. These are becoming more common as companies look for cheap images for their advertising. Note that usage policy is not the same as the policy on returning your photos. Returning the mountain of submissions is a major pain; this is covered in more detail below.
Don't send originals (unless later requested for verification). Many contests do not return entries, as it's just too time-consuming. Some will return entries if you include either mailing materials and postage or a fee (which, if reasonable, is of course legitimate, so long as the actually follow through). It is much safer, and usually cheaper, to send copies if a print or slide is requested, and let the sponsor keep your entry, especially if they will consider it for later use (and compensation) if you do.
It would seem obvious that you should submit your photo in the requested format - except that, in nearly every contest I've judged, several entrants do not! You won't get anywhere if you don't follow the rules. The first step is submit the requested format, and follow the instructions to the letter.
Right behind that, and so important that it isn't even "number two," is to make sure your photo is technically well-done. These first steps will help to insure that your entry survives the first round, where unsuitable entries are weeded out.
However you may feel about a photo, perhaps because of the subject or the trip you were on, you need to look at it carefully. It might help to get a friend to help. Pictures that are blurred, out of focus, badly exposed, and so on, will not make it past the first round. If you deliberately intented to do something along those lines, such as a pan shot, selective focus on an unusual feature, or a silhouette, make sure it's clear from the picture itself what you are doing. Other flaws are a tilted horizon, a background that distracts from the photo -- like a pole growing out of an odd place, a cluttered foreground, the subject too small (or cut off).
After that point, the more serious discussions begin. Although there are many guides and "rules" of composition and technique available, judges are looking for something that stands out, and just what that means cannot be defined easily. A good photo tells a story about itself, and will often have some display of technique or composition that sets it apart. Some of it is also personal taste.
You shouldn't take it hard if you don't win, because judges may be looking for something else: a favorite road of their own if you've entered a rail photo contest, or a car instead of a train if you've entered a more general contest. For all the bad photographers out there, there are also a lot of fairly decent ones, so the competition is stiff.
