I don't really know what you're trying to do, but if it's a DIP and the boards are drilled, use a wire-wrap socket placed through drilled pads in the riser to provide pins into the pads on the host board? Those milled legs can be pretty sturdy.
Looking at DIP IDC connectors might give you other ideas;
this company got creative with single-row pin headers, which seems to work. Of course if you need to clip over a PLCC or something, you'd need something ridiculous like
this.
