Here are a few challenging word problems from Singapore:
I did fine on the 3rd-grade problems, but I stumbled a bit on the 4/5th-grade “How much sugar…” problem. The toy cars were tricky, but manageable. I misread the problem with the chocolate and sweets at first — I think of chocolates as a sub-category of sweets, but in this problem they are totally different. (Perhaps “sweets” are what I would call “hard candy”?) Finally, I had to resort to algebra for the last two Grade 6 questions.
How many can you solve?
Denise Gaskins' Let's Play Math 