I live almost 20 miles away, and so generally haven't the foggiest what the town's sights actually look like, so my chances of winning usually hover around nil. In theory.
Two weeks ago, they gave a clue consisting of the latitude & longitude coordinates of the location; I dumped them into Google Local to get the location pinpointed on a satellite image with streets marked, guessed the only village landmark I know of in that area of town--a half-scale replica of the Leaning Tower of Pisa--and thereby got in the first correct guess and won a box of chocolate truffles.
This week's was another one that required a clue to get a winner; this time the clue was simply a recropped picture. I had absolutely no idea, and on a lark put in this as my guess: "It's next to a big rock, on a brick walkway, probably in a park somewhere."
Much to my surprise, my name turned up on the list of runners-up, and so I got a Hershey bar.
Moral of the story: When in doubt, make the judges laugh.
(The location turned out to be small boulder that holds a memorial plaque--and is about 20 feet from the library's front door.)
Feudalism: Serf & Turf