Around here, the LBSs start putting the previous years and any older stock on clearance in late August, usually. I got about 25% off by watching those sales. My LBS also has a week-long late-August sale with 20% off everything but bikes. This is great for getting all the little bits you might want, like a pump, CO2 inflators, seat bag, spare tubes, patch kit, shoes & pedals, jersey, shorts, etc.

Of course, I'm in Florida and we don't have an off-season.